In this episode of Think Like an Owner, host Alex Bridgeman sits down with John Peterson for a wide-ranging conversation on entrepreneurship, adaptability, and building a service business from the ground up. John traces his path from professional golf—where he saw firsthand the parallels between sports and entrepreneurship—to flipping houses during COVID and ultimately founding Westoplex Garage, a garage door and epoxy floor company based in Fort Worth, Texas. With honest pricing and a service-first mentality, John shares how he grew the business from a two-man team in his garage to a multi-division operation poised for expansion into new markets.

We discuss:

• How John's early golf career shaped his entrepreneurial mindset and approach to financial risk

• Why a $2,200 garage door quote sparked the idea for a new business

• The importance of interpersonal skills over technical experience in hiring technicians

• Lessons learned from starting a service company from scratch versus acquiring an existing one

• The strategic decision to expand into Baton Rouge and the advantages of using private aviation for business

A must-listen for operators and builders interested in the intersection of blue-collar service and entrepreneurial scale.

Follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

John on X

Alex on X

Westoplex Garage

Topics:

(00:00:00) - Intro
(00:01:10) - John's career as a pro golfer
(00:14:53) - Pivoting into the garage door business
(00:23:48) - Epoxy vs. concrete floors
(00:25:36) - Latest tech innovations in garages
(00:27:53) - The self-storage market
(00:33:05) - Building a new customer funnel
(00:36:48) - Training new technicians
(00:37:55) - Recruiting talent
(00:40:31) - What to look for in hires
(00:43:38) - Why people leave the industry
(00:48:02) - Opening a Baton Rouge office
(00:52:35) - Growing pains
(00:55:17) - What are you most excited about in the next year?

Alex (@Aebridgeman) is joined by Richard Emery (@Richardemery2).

In this episode, my guest is Richard Emery, who has held various notable positions in business aviation sales at brands like Canadair, Bombardier, Gulfstream, and Hawker Beechcraft.

Richard shares his experiences in different sales cultures, managing high-performing teams, and participating in brand turnarounds. The discussion covers his leadership style, team management, and the skills relevant to CEOs.

Additionally, the episode includes entertaining stories about selling aircraft to unique clients, making it an engaging listen for anyone interested in business aviation and sales.

Links:

Richard on LinkedIn

Topics:

(00:00:00) - Intro

(00:01:31) - Richard's career and background

(00:04:41) - How do you organize a high-performing sales team?

(00:14:00) - Identifying ideal customer profiles

(00:23:49) - Developing a customer outreach team

(00:27:44) - Having discipline and focus on a sales team

(00:38:28) - Leadership philosophies

(00:50:08) - What can CEOs do to make their sales teams more effective?

Watch the full episode here: https://youtu.be/UTNl0xeSgZY

Ep.177: Alex Bridgeman (@aebridgeman) is joined by Sieva Kozinsky (@sievakozinsky).

My guest on this episode is Sieva Kozinsky, co-founder of Enduring Ventures, a holding company founded in 2019 with 17 acquisitions to date. Sieva and I met at a dinner following the Berkshire Hathaway meeting in Omaha, his first time attending the meeting. A theme from our first conversations in Omaha that continues through this episode is long-term thinking being a huge advantage, and that compounding happens everywhere. Reputation, lessons, and learning - well beyond capital alone.

We talk about Sieva's background as a founder and how it impacts his role at Enduring Ventures, how he discovered he is a better buyer than a builder, great companies and founders he's studied and taken lessons from, and much more. Enjoy!

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Sieva on LinkedIn

Sieva on Twitter

Enduring Ventures

Founders Podcast

Titan: The Life of John D. Rockefeller by Ron Chernow

The Gambler: How Penniless Kirk Kerkorian Became the Greatest Deal Maker in Capitalist History by William Rempel

Timestamps:

(00:03:53) Belief Documents

(00:08:39) Long-termism trends

(00:11:22) Takeaways from the Berkshire Event

(00:20:02) Helping employees & executives think and behave like an owner

(00:25:44) Being a Buyer vs. Builder

(00:32:36) Culture Index

(00:35:24) The importance of having experience as a founder/operator to succeed at Enduring

(00:44:18) Pareto Prinicples

(00:53:45) Habits, tactics, and learnings from biographies on great founders and companies

(01:08:14) What strongly held belief have you changed your mind on?

(01:09:34) What's the best business you've ever seen?

Ep.177: Alex (@aebridgeman) is joined by Mark Stiving (@Stiving).

My guest on this episode is Mark Stiving. Mark is a pricing expert and consults with companies on developing stronger pricing and product positioning strategies. Our discussion today on pricing is wide-ranging from the purposes of pricing, value-based pricing, segmentation, and who's responsibility pricing is in an organization. What I loved about this episode is getting a distilled view on pricing based on hundreds of case studies over decades of work, giving tons of great lessons for the CEO listener.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links

Mark Stiving on LinkedIn

Impact Pricing LLC

Books by Mark Stiving

Never Split the Difference by Chris Voss

Invest Like the Best: Henry Schuck - Building Zoominfo

Van Westendorp's Price Sensitivity Meter

Timestamps

(00:03:07) Mark's early career in pricing

(00:11:09) The fundamental purposes of pricing

(00:16:06) How to evaluate your product pricing, the CEOs role, and incentivizing Sales

(00:26:12) Tools for Salespeople

(00:28:14) Teaching Behavior in Sales

(00:30:25) Practices for communicating with customers

(00:36:44) The scientific process for determining the price of something

(00:40:57) When to segment customers

(00:48:30) Positioning plans for pricing within websites and calls

(00:51:59) Companies that have stellar segmentation and pricing pages

(00:53:56) Luxury Pricing

(00:56:12) How to raise prices

(00:59:33) SaaS Contracts

(01:03:49) AI in Pricing

(01:06:18) What strongly held belief have you changed your mind on?

(01:07:39) What's the best business you've ever seen?

Ep.175: Alex (@aebridgeman) is joined by Philip Hussey (@philipdhussey).

My guest on this episode is Philip Hussey, CEO of Outerland, a landscape maintenance, new build, and snow removal business in Cape Cod, owned by Chenmark. Philip took the CEO role through Chenmark's GVP program in January 2022. A concept he spends a lot of time thinking about that we discuss in detail is their focus on their internal customer, i.e., the Outerland team.

They believe by serving and delighting their internal customers, they will do the same towards their external customers. I love the concept and think CEOs of any business can benefit from hearing their philosophy. We also talk about being the high-end service provider and what that looks like, recruiting for high-end and customer service-oriented companies that Phillip admires.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Outerland

Chenmark

Philip on LinkedIn

Timestamps

(00:03:44) Outerland and executing a rebrand

(00:08:11) Describing the ideal Outerland customer

(00:09:58) How Outerland differentiates themselves

(00:12:26) Building trust with customers

(00:16:37) Recruiting talent

(00:22:16) Internal customers

(00:26:10) Off-season opportunities

(00:28:58) Upsell strategies

(00:32:05) Studying other companies that create "Wow" moments

(00:43:28) Making sure Management gives a damn

(00:46:20) What strongly held belief have you changed your mind on?

(00:48:05) What's the best business you've ever seen?

I want to tell you about our audience survey we are currently running. These surveys help us create the best content for listeners and better understand your needs and interests. Thank you in advance for sharing your feedback, we greatly appreciate it. After 30 days we are giving $250 cash to 4 survey responders, just add your email at the end of the survey.

Take the survey here: https://bit.ly/3QLBB1N

Ep.174: Alex (@Aebridgeman) is joined by Alex Thinath (@Alex-Thinath) and Nikita Sunilkumar (@Nikita-Sunilkumar).

This episode is the second in our Launch Series, a partnered series with Pacific Lake Partners and Trilogy Search Partners, focused on starting a search. We walk through the various phases before and after the search begins, with key questions and best practices on how to approach each phase. I'm joined by Alex Thinath, a current searcher backed by both Pacific Lake and Trilogy, and Nikita Sunilkumar, an entrepreneur in residence at Trilogy. In our discussion, we also discuss differentiation as a searcher, choosing investors, key KPIs and metrics to watch, and measuring success.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Trilogy Search Partners

Pacific Lake Partners

Timestamps

(00:02:22) Introducing Nikita and Alex

(00:04:54) Activities and questions in the 3-12 months leading up to the Search

(00:10:35) Industry research 

(00:14:35) Cap table and investor selections

(00:22:53) Drafting a PPM

(00:32:34) Daily activities and tools to use one month into a Search

(00:41:55) How Searchers should pitch themselves

(00:47:42) Getting into your groove: 6 months into a Search

(00:54:12) KPIs and benchmarks to hit during Search

(00:59:50) Utilizing interns and VAs

(01:05:59) Final thoughts

Ep. 173 Alex Bridgeman (@Aebridgeman) is joined by Clayton Collins (@ClaytonACollins).

Today's episode was recorded live in late April 2023 at SMBash in Austin, Texas, with my boss, Clayton Collins, CEO of HW Media. We opened up talking about how the role came together, but for a short preview, I took a Chief of Staff role with HW Media in March 2022 to help build a media and data company in the housing industry.

It's been an exciting journey with a steep learning curve that I'm thoroughly enjoying. In the episode, we talk about acquiring within your industry, the acquisition journey at HW Media, the case for acquisitions as a compliment to organic growth, what a bad acquisition looks like, and so much more. This event is fantastic for all those looking to pursue entrepreneurship through acquiring a company, and I hope to see you all at next year's event.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

HW Media

Clayton on Twitter

SMBash

Timestamps

(00:03:56) Introducing Clayton 

(00:05:36) The Chief of Staff role

(00:08:26) Growth through Acquisition

(00:11:15) HW Media's 3 acquisitions

(00:14:53) What Clayton looks for in potential acquisitions

(00:18:47) Evaluating a team inside a company being acquired

(00:20:33) Building relationships in an industry

(00:22:00) Avoiding train wreck acquisitions

(00:26:13) Debt

(00:27:24) Advice for CEOs wanting to build a repeatable acquisition process

#172: Alex (@aebridgeman) is joined by Doug Cook (@DougCook).

This episode was a live recording at a joint event in Chicago between the Booth and Kellogg Business Schools. My guest was Doug Cook, Chairman of several companies throughout Illinois in windows and siding, chimney care, garages, elevators, and more; With windows and siding being his most notable business in Feldco. Doug gives a deeper walkthrough of his very impressive and entrepreneurial career at the start of our conversation. We also talk deeply about empathy and how to develop it as a skill, empathy when building a team and selling to customers, trust and respect as a CEO, lessons that are the hardest to be taught, and much more. Doug is a fantastic person, I think that will come through loud and clear throughout the episode.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links

Doug on LinkedIn

Feldco

Jack Welch Books

YPO

Timestamps

(00:04:47) Doug's background and career

(00:12:10) Lessons Learned: Less is more

(00:16:50) Common Skillsets in CEOs

(00:28:09) Developing empathy as a skill

(00:34:30) Finding the line between becoming too friendly with employees

(00:35:14) Developing empathy with customers

(00:37:10) The CEO's role with customers

(00:40:37) Refining a Product line

(00:47:49) Difficulties in Growth through Acquisition

(00:50:37) Building Trust and Respect with Employees

(00:56:33) Are there any CEOs you admire?

(00:58:32) What's a strongly held belief you've changed your mind on?

(00:59:49) What's the best business you've ever seen?

Ep. 171: Alex (@aebridgeman) is joined by Justin Nassiri (@JustinNassiri).

My guest today is Justin Nassiri, founder and CEO of Executive Presence, a managed social media service for ambitious CEOs, with a focus on LinkedIn today. We talk about why CEOs should care and focus on building a social media following, and how CEOs can optimize their social presence, including a walkthrough of the most important things to optimize on your LinkedIn profile. We also compare the top platforms for CEOs, LinkedIn and Twitter, and the pros/cons of each and where to start.

Justin also draws on his experience being a founder of two prior companies, Captivate and StoryBox, to be a more effective and balanced CEO in his current business. He has a lot of lessons learned and advice for CEOs looking to expand their reach and improve individual performance. This episode was super interesting and rich with actionable ideas and I think you'll come away with a lot to apply to your own company.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Justin on LinkedIn

Executive Presence

Beyond the Uniform Podcast

Thumbtack

SmartShoot

Timestamps

(00:04:05) Justin's career prior to Executive Presence

(00:09:47) Capturing authenticity in a client

(00:15:04) Thoughts on different Social Media platforms for CEOs

(00:19:06) How to use LinkedIn in a more optimized fashion

(00:23:15) Growth pattern differences between Twitter & LinkedIn

(00:24:58) How to optimize your profile

(00:36:51) How CEOs can benefit from an increased presence on LinkedIn?

(00:41:32) Being Transparent on Social Media

(00:47:42) Lessons learned from founding 3 companies

(00:57:47) Finding work-life balance and creating high-quality work

(01:03:54) What's a strongly held belief you've changed your mind on?

(01:05:10) What's the best business you've ever seen?

I want to tell you about our audience survey we are currently running. These surveys help us create the best content for listeners and better understand your needs and interests. Thank you in advance for sharing your feedback, we greatly appreciate it. After 30 days we are giving $250 cash to 4 survey responders, just add your email at the end of the survey.

Take the survey here: https://bit.ly/3QLBB1N

Ep. 170: Alex (@Aebridgeman) is joined by Aaron Perrine (@AaronPerrine) and Kevin Oxendine (@KevinOxendine).

Today's episode is the first in our new seven-episode series titled Launch Series, in collaboration with Trilogy Search Partners and Pacific Lake Partners. This series is meant to be a guide to preparing a search entrepreneur for their upcoming CEO role, the next major step in their career. Our episodes will focus on topics such as starting up a search, deal structuring, seller relationships, first hundred days, governance, and much more.

This first episode focuses on conducting effective industry research with guests Aaron Perrine and Kevin Oxendine, Partners of Trilogy and Pacific Lake, respectively.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Aaron on LinkedIn

Kevin on LinkedIn

Trilogy Search Partners

Pacific Lake Partners

Grata

Listen to last year's Trilogy Search Series on Spotify

Timestamps:

(00:02:40) Kevin and Aaron's background and careers

(00:04:37) How Searchers are approaching Industry research and focus

(00:19:17) Evaluating M&A activity in an industry

(00:24:56) Characteristics or factors that remove industries from consideration for investment

(00:31:31) Finding Industry experts 

(00:36:54) How Searchers can best tell their own story

(00:42:09) The process of doing online research before getting on the phone with owners

(00:45:50) Writing a phenomenal PPM

(00:49:14) Tools for Searchers Doing Industry Research

(00:51:12) Different Levels of Industry Research

Ep 169: Alex (@aebridgeman) is joined by Amir Haboosheh (@amirhaboosheh)

My guest on this episode is Amir Haboosheh, Co-Founder and CEO of Snowball Industries, a home services holding company with 4 portfolio companies today. Their vision is to build a permanent, publicly traded home for these companies, and Amir and I talk extensively about what an IPO looks like and the benefits and tradeoffs it brings. 

We also talk a lot about empathy, a skill ambitious CEOs cannot get enough of, lessons from Amir's family on empathy, and how he coaches new managers on empathy and leadership. This conversation had a lot of depth and I think you'll be able to take away many of these lessons to your own company.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Snowball Industries

Amir on LinkedIn

Buffet: The Making of an American Capitalist by Roger Lowenstein

Berkshire Hathaway Shareholder Letters

$FIX - Comfort Systems

John Wilson on Think Like an Owner

Color Code

Timestamps:

(00:00:00) Intro

(00:03:45) Favorite Warren Buffet Lessons: Reputations

(00:07:28) Being flexible in purchase agreements

(00:09:31) Snowball's Origin and business strategy

(00:14:52) Home Services companies going Public

(00:16:48) Revenue required to go Public

(00:19:27) How the role of the CEO changes through company growth and Going Public

(00:25:45) The power and importance of Empathy

(00:41:28) Screening for empathy in candidates

(00:44:14) Color Code

(00:49:06) Giving feedback

(00:53:35) Leaning on a board for expertise

(00:57:29) What strongly held belief have you changed your mind on?

(01:00:01) What's the best business you've ever seen?

Ep. 168: Alex (@aebridgeman) is joined by Daniel Hudspeth (@danielhudspeth).

My guest today, Daniel Hudspeth, is the CEO of Discover Health, a concierge medical practice business with locations in California, Boston, and soon to be Seattle. During his search Daniel did extensive research on private pay healthcare and eventually developed a thesis to acquire multiple concierge practices across the country.

We talk about this pivot during his search, what the concierge model looks like for patients and doctors, why it's an attractive business as an investor and operator, and what growth could look like over the coming years. Given my mom is a family physician, this episode felt close to home and I enjoyed the chance to connect with an entrepreneur like Daniel who's looking to build a better model in patient healthcare.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Discover Health

Concierge Medicine Today

ROAMD

The Predictive Index

Founders Podcast - Yvon Chouinard: Patagonia's Founding Principles

Let My People Go Surfing by Yvon Chouinard

Topics:

(00:00:00) - Intro

(00:03:23) - Daniel's Search Journey

(00:14:31) - Investor hesitations force the Search to go longer

(00:17:28) - Recruiting Doctors to the Organization

(00:25:57) - Churn dynamics

(00:29:47) - Staffing requirements

(00:31:45) - Establishing a playbook for how these businesses are run

(00:35:18) - Concierge-centric Podcasts

(00:37:23) - Defining Executive roles

(00:40:09) - How the CEO role has changed

(00:43:06) - Utilizing peer networks

(00:46:05) - Tools for hiring and recruiting

(00:50:13) - What strongly held belief have you changed your mind on?

(00:52:47) - What's the best business you've ever seen?

In this episode of Think Like an Owner, I sit down with Hill Hamrick, Co-CEO of Central Storage & Warehouse, to explore how he and his team run a complex, high-volume cold storage business that ships hundreds of millions of frozen food products across North America every year.

We dive into how Hill and his co-CEO, Sam, transitioned from first-time owners into strategic leaders of a 24/6, labor-intensive operation. Hill shares how they learned the business from the ground up, why building trust with frontline employees was critical in the early days, and how his experience in the Marine Corps continues to shape his leadership approach.

We also get into:

• How EOS helps align a 200+ person team across multiple locations
• Why data is the backbone of operational decision-making
• Lessons in pushing ownership and problem-solving to the front lines
• The difference between wartime and peacetime CEO mindsets
• Strategies for scaling culture and priorities while still in motion

Hill also opens up about the challenges of system migrations, prioritizing as a CEO, and the discipline required to avoid shiny-object distractions when building long-term value. This episode is a masterclass in leading through complexity and creating alignment in fast-moving, blue-collar businesses.

Links:

Hill on LinkedIn - https://www.linkedin.com/in/hill-hamrick-094807a0/

Central Storage and Warehouse Co. - https://www.csw-wi.com/

Pacific Lake Partners - https://www.pacificlake.com/

Trilogy Search Partners - https://trilogy-search.com/

Topics:

(00:00:00) - Intro

(00:06:55) - Introducing CSW and Hill

(00:08:45) - Priorities Frameworks

(00:12:23) - Most Effective Ways to Build Trust with a Team

(00:18:52) - Challenges in Creating a Synchronous Team

(00:22:37) - Making System and Software Migrations

(00:27:04) - Moving Decision-Making Down the Org-Chart

(00:33:48) - Matching CEO Mindsets with Organizational Needs

(00:44:23) - Board Member Advice

(00:47:42) - Prioritization Evolutions

(01:02:10) - Lessons from the Military

Episode 167: Alex Bridgeman (@aebridgeman) is joined by Chris Hoffman (Chris-Hoffman).

My guest, Chris Hoffmann, is the President and CEO of Hoffmann Brothers, a home services business based in St. Louis. Hoffmann Brothers have scaled from $10 million in 2015 to over $100 million in revenue in 2023. We talk about how that journey happened, their experience building executive teams, investing in people through a training university they started for ongoing training, and investing activity for home services today.

We also talk about what perpetual non-private equity ownership enables them to do, including their unique strategy for managing cash investments and liquidity as a growing family office. This was a ton of fun for me and I hope you enjoy this conversation as well.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at www.AlexBridgeman.com

Links:

Chris on LinkedIn

Hoffmann Brothers

NexStar Network

Chapters:

(00:03:38) - Hoffman Training University & NexStar

(00:08:26) - Enabling scale and revenue growth

(00:10:55) - Differences in PE-backed company structures

(00:14:25) - Retention and morale-boosting tactics

(00:17:59) - Leadership team composition

(00:21:17)- Surfacing high-performers & evaluating management teams

(0:28:53) - Using Search Firms to find talent

(00:30:25) - Choosing an Executive Search firm

(00:33:30) - Financial sponsor interest in the HVAC and Home Services market

(00:36:15) - Reasons Consolidators are failing

(00:38:41) - Debt, Public Equity Strategies & Fund Investing

(00:48:00) - Goals for the family office

(00:49:47) - Building new locations from scratch vs. acquiring existing companies

(00:55:37) - Acquiring a school

(00:58:53) - Changing strongly held beliefs

(00:59:54) - Chris' favorite business

Episode 166: Alex (@aebridgeman) is joined by Ed Redden (@Edward-Redden).

Ed and his partner Justin Vogt are former podcast guests from episode 59 where we talked about starting Evermore Industries, an industrial services holding company. Last year they acquired AVUITY, based in Cincinnati, which sells physical commercial office sensors that detect motion, temperature, humidity, and more, along with a data and analytics subscription.

Ed and I talk about making the first acquisition in a holding company strategy, working at the intersection of hardware and software, talent planning and sales development, and life running a company while being a new parent. Enjoy!

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at www.AlexBridgeman.com

Links:

Ed on LinkedIn

AVUITY

Evermore Industries

Topics:

(00:00:00) - Intro

(00:03:23) - Acquiring AVUITY

(00:07:20) - Characteristics that make a great business to acquire

(00:11:38) - Competing with Venture-backed businesses

(00:13:34) - Advice from investors

(00:17:25) - Accelerating Revenue Growth

(00:22:44) - Measuring customer ROI

(00:25:09) - Data application between customers

(00:29:30) - Hiring plans

(00:36:33) - Growth pain points

(00:38:55) - Learning to sell

(00:40:26) - Life as a new parent & operator

This is the third and final episode in our three-part series on Chenmark, a highly successful small business holding company founded in 2015. Today they have acquired 11 operating companies, completed 30+ acquisitions when including add-ons, and have over 600 employees today.

This third episode takes a deep dive into their CEO recruiting function and what has to happen to keep Chenmark on its growth trajectory. We discuss their GVP program where they recruit young hungry leaders to eventually be placed in CEO roles, their GA program for associate-level recruiting, and earning the right to take risks and what that means for them today. I hope you enjoy this third part of the series with Trish Higgins and James Higgins.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Chenmark

Trish on LinkedIn

James on LinkedIn

Will Thorndike on Invest Like the Best

Legacy by James Kerr

Chenmark Series 1

Chenmark Series 2

Topics:

(00:04:51) Earning the right to take risks

(00:11:10) Accelerating acquisitions and faster processes

(00:13:04) Expanding capacity beyond headcount growth

(00:17:25) Reinvestment in current companies vs. new platforms

(00:22:08) Not having a full-time person searching for deals

(00:26:13) Chenmark's GVP Associate's Program

(00:36:31) Hiring CEOs and Operators

(01:04:16) How to make Chenmark be successful for another 20 years

(01:07:17) How to carry on a Newsletter long-term

Please take 2 minutes to complete this audience poll and give feedback on the podcast

This episode is the second in a three-part series we are running on Chenmark, a highly successful small business holding company founded in 2015. Today they have acquired 11 operating companies, completed 30+ acquisitions when including add-ons, and have over 600 employees today.

This second episode focuses on their operating ethos, culture, and incentive structures. We discuss meeting cadence and formats across the company, the use of debt, CEO incentive models, broad incentives beyond CEOs, and lessons learned from building and maintaining good cultures. I hope you enjoy this second part of the series with James Higgins and Palmer Higgins.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

James on LinkedIn

Palmer on LinkedIn

Chenmark

The Weekly Thoughts Newsletter

Listen to Part 1 of this series here

Topics:

(4:26) - How do your core values extend to your portfolio companies?

(6:13) - What are some ways you learn about the culture and core values of a company you acquire?

(8:32) - Is there a wide range in terms of how quickly teams can adapt to these new core values? 

(10:52) - How do you assess the willingness to change the culture in new ownership?

(13:57) - Are there a set of recurring meetings you have in the early days of ownership?

(20:02) - Is there an ideal set of principles and tools you're looking to reach internally for portfolio companies?

(21:26) - Is there a way you're storing past decisions in a database?

(27:43) - What's the next piece of the communication cadence journey for you?

(29:00) - How many acquisitions are you making per year?

(32:34) - Are there any other flywheels you didn't anticipate coming to fruition?

(35:14) - What's been the evolution of CEO incentives?

(38:53) - Chenmark's stock purchase program

(42:54) - What companies do you look to for inspiration on compensation plans?

(44:30) - Does the incentive plan change across roles?

(47:06) - Are there any negative consequences of a Free Cash Flow Compensation plan?

(51:51) - What's the philosophy behind the FCF compensation plan?

(55:18) - Are there any other common principles around compensation or budgets that don't fit with what you want to do?

Please take 2 minutes to complete this audience poll and give feedback on the podcast

This episode is the first in a three-part series we are running on Chenmark, one of the most well-known and studied holding companies in the entrepreneurship through acquisition world. And for good reason! Since its founding in 2015 they have acquired 11 operating companies, completed 30+ acquisitions when including add-ons, and has over 600 employees today.

This series is not meant to be a one-stop-shop for everything Chenmark. The Higgins' have appeared on Invest Like the Best, there is a fantastic case study by A.J. Wasserstein about them, and they share their thoughts every week through their Weekly Thoughts newsletter, which is one of my favorites. Instead, this series is meant to dive into topic gaps, where I am most personally curious, and areas of change for Chenmark.

For this first episode, we cover the risk/reward of their path early on, founding ideals, and various pivots and challenges in starting Chenmark. The second episode focuses on their operating ethos, culture, and incentive structures. The third and final episode takes a deep dive on their CEO recruiting function and what has to happen to keep Chenmark on their growth trajectory. I hope you enjoy the series, please enjoy this first episode with Trish Higgins and Palmer Higgins.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Trish on LinkedIn

Palmer on LinkedIn

Chenmark

Trish and James Higgins on Invest Like the Best

The Weekly Thoughts Newsletter

Topics:

(5:11) - How did you come up with the core values for Chenmark?

(12:58) - Has establishing these values made it easier to communicate change?

(14:06) - How did you each consider pursuing the path of SMB?

(20:57) - How has your thinking evolved since running Chenmark?

(22:09) - Have you found that having competition encourages you that you can build something really successful in this industry?

(24:45) - What skills translated over best from Finance to SMB?

(28:07) - How did your prioritization of tasks change when you made this jump?

(33:00) - What are some ways you make health a priority?

(42:01) - What were some process improvements you made in your first 3 acquisitions?

(46:39) - What have been some helpful tools for evaluating CEOs?

(49:22) - How does performance factor into evaluations?

(51:05) - In the Search world, what changes have you observed the most strongly over the past few years?

(54:42) - Are you enjoying yourself?

(57:26) - What do you like and dislike about your roles?

Please take 2 minutes to complete this audience poll and give feedback on the podcast

My guests on this episode are Jalen Ross and Orlando Remak, cofounders of CAM Collective, a holding company for association management companies like HOAs founded in April 2022. Today they have four member companies. I was lucky enough to meet Orlando during a trip to Ohio two years ago before he had started CAM Collective and have thoroughly enjoyed getting to know him and Jalen.

We talk about being intentionally decentralized while remaining focused on one industry and business model, focusing on growing revenue vs achieving cost savings, looking for ways to automate processes, hiring at a holding company level, and creating a partnership vs. being solo entrepreneurs.

I'm sure you'll be able to tell very quickly, but Jalen and Orlando beyond being partners are also clearly great friends and are very fun to chat with. I hope you enjoy this episode with Jalen and Orlando.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

The CAM Collective

Orlando on LinkedIn

Jalen on LinkedIn

Topics:

(4:22) - What is the CAM Collective?

(5:09) - What kind of content would you make around CAM?

(6:41) - What are some crazy HOA Management stories?

(11:47) - Why were HOAs interesting to you?

(15:48) - What level of churn do you see in your business?

(17:27) - What are some keys to maintaining HOA relationships?

(20:58) - How does pricing power work in HOA Management?

(22:16) - How have you approached the decentralized nature of the company?

(25:36) - What value propositions did you see were missing in this market?

(31:19) - How do you maintain such a high level of care?

(33:04) - What are some revenue lines and growth opportunities you seen with HOA Management companies?

(37:13) - What are some no-code or automation tools you've found to be effective?

(40:55) - What's the philosophy around having smaller teams?

(50:31) - What are the pros and cons of doing this as a partnership?

(53:55) - Were there any exercises you did on trying to find a career you would enjoy and feel fulfilled in?

(1:02:51) - What are some strongly held beliefs that you've changed your mind on?

(1:06:36) - What's the best business you've ever seen?

(1:10:52) - More on CAM Collective

Please take 2 minutes to complete this audience poll and give feedback on the podcast

Daniel Reese is my final guest on the CEO series with early career CEOs. Daniel acquired IntellaTriage in November 2019 after a military career and searching with a distinct thesis. IntellaTriage handles after-hours calls for providers, senior living businesses, and others with a remote nursing team.

Daniel and I talk about growing a business that felt very much like a startup early on, advice for new CEOs, scaling teams, and finding a balance in his life as CEO. We also talk about working on submarines, which could be an entire podcast in its own right.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Daniel on LinkedIn

IntellaTriage

Traction by Gino Wickman

Scaling Up by Verne Harnish

Carl Streck on Think Like an Owner

Topics:

(4:09) - Daniel's Military career

(6:57) - What was the thesis behind your Search?

(8:49) - What was the state of the business when you took over and what did your first 6 months look like?

(10:47) - How was management structured upon acquisition and how did you adjust it?

(12:01) - How did you prioritize hiring for management positions?

(13:19) - What do you feel went well in the first 2 years of ownership and what went poorly?

(15:08) - What did you need to do to enable revenue growth?

(16:34) - What decisions were made in the first 2 years to set up this growth you're having now?

(18:07) - Has client communication improved your customer churn?

(21:18) - Do you have any feedback mechanisms with customer communication?

(23:28) - How has your ability to focus on long-term projects changed?

(25:22) - How do you go about setting goals?

(26:45) - Has the business changed dramatically since your acquisition?

(28:04) - What needs to happen to scale the company?

(29:22) - How has your life changed since becoming CEO?

(31:31) - How do you approach the way you phrase things to your team as the CEO?

(36:35) - What advice do you offer early-career CEOs?

(38:36) - What do you consider when putting together a board?

(40:11) - What strongly held belief have you changed your mind on?

(41:38) - What's the best business you've ever seen?

Please take 2 minutes to complete this audience poll and give feedback on the podcast

This episode is the second in our CEO series with early career search CEOs in their companies. Today I'm joined by Adam Ilowite and Michael Upex, CEO and President of Axero Solutions, respectively. Axero is a digital workspace platform for internal communication, collaboration, and knowledge sharing that was acquired by Adam and Michael in July 2021.

We discuss the timing of making changes in the business, creating a budget from scratch, talent planning, and managing an incredibly steep learning curve, among various other operations topics.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Axero Solutions

Michael on LinkedIn

Adam on LinkedIn

Frank Slootman on Invest Like the Best

Topics:

(4:47) - What was your experience Searching and how were the first few months after the acquisition?

(7:14) - Were there any skills from your careers in Consulting or Investment Banking that played a role in your Search?

(8:55) - What advice did you get from investors or peers on how to handle your first year within the business?

(11:04) - Was there any challenge or learning curve that stands out from that first year?

(16:52) - How did you go about learning ideal process implementation?

(22:52) - What lessons on change management have you learned?

(23:51) - How has your mindset changed as you navigate your second year of ownership?

(26:51) - What are your top 3 priorities?

(28:07) - What's your philosophy for putting together budgets and hiring plans?

(29:44) - How do you decide on edge-case expenses when you're structuring a budget?

(31:49) - How did you think about what positions were needed when creating your hiring plan?

(34:38) - What are some common errors or omissions you've seen in budgets that you try to avoid?

(36:05) - What are your thoughts on filtering advice and who you should be listening to?

(38:18) - How does industry factor into the types of people you reach out to for advice?

(40:10) - Have you found value in going to industry conferences or trade publications?

(42:28) - What excites you the most about running this business in 2023?

(45:05) - What strongly held belief have you changed your mind on?

(48:33) - Are there any entrepreneurs or CEOs that you study and admire?

(49:49) - What's the best business you've ever seen?

My guest, Ryan Galea, is the first guest in a CEO series I'm doing with search CEOs who acquired their companies within the last 3 years and have early lessons and emotions in their very recent, or current, memory. The series aims to learn strategies and hear stories from early career CEOs about how to manage the first couple of years running a new company. 

Ryan acquired VoiceFriend in August of '21, a communications platform for nursing homes and senior living facilities. Then less than a year later acquired a second business Caremerge which offers engagement software for senior living. Ryan and I discuss managing people and tasks, internal communication, change management with an acquisition vs a merger, and what's gone differently than expected.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Ryan on LinkedIn

VoiceFriend (Now Icon)

Caremerge

Topics:

(4:25) - Ryan's career

(10:48) - How do you Prioritize tasks and which ones to delegate?

(11:59) - What's your process for training someone to do a task you've previously done yourself?

(13:56) - How do you think about the way you phrase things given your role as CEO?

(16:01) - What made you decide to get a law degree? 

(17:20) - Has your time horizon shifted as you've been able to delegate more of the business?

(18:37) - How has this shift affected your priorities?

(20:09) - Was there a critical point that allowed you to become more strategic as a CEO?

(22:09) - What are some of your biggest learnings in the process of integrating acquisitions?

(24:08) - What were some of the differences between the initial acquisition vs. the merger?

(28:46) - What strategies do you use to clear uncertainty?

(29:43) - What has been your best win and toughest loss during your first 2 years?

(31:33) - What kind of advice would you offer a first-year CEO?

(33:28) - In what ways has your life as CEO turned out differently than you thought it would?

(34:12) - What's a strongly held belief that you've changed your mind on?

(35:23) - What are some ways you try to identify really motivated people?

(36:23) - What's the best business you've ever seen? 

This is the last of a six-episode series with Trilogy Search Partners focused on Search, Search-backed acquisitions, and small business operations. Today we have a great conversation with Stijn Hendrikse, an operating partner at Trilogy.

As an author of T2D3.pro, serial entrepreneur, and marketing leader, Stijn has contributed to the success of 10+ startups as a C-level executive, including the Chief Revenue Officer of Acumatica and CEO of MightyCall, a SaaS contact center solution.

Stijn founded Kalungi - the global leading Growth-as-a-Service provider focused solely on B2B SaaS companies, and Amy.us, an AI-powered conversation platform that allows small business owners to service their customers better.

Before focusing on startups, Stijn led global SMB Marketing and B2B Product Marketing for Microsoft's Office platform.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Stijn on LinkedIn

Trilogy Search Partners

Browzwear

Topics:

(1:53) - Breaking down the SAAS business model

(4:22) - What are some of the SAAS companies and marketing teams you've been a part of over your career?

(7:20) - What led you to ultimately work with Search Funds?

(11:22) - What kinds of companies do you encourage Searchers to look for?

(13:50) - How do you value the effectiveness of a marketing function in a company?

(20:03) - Where can early CEOs improve on pricing?

(25:58) - Do you recommend any proactive communication cadence with customers?

(30:45) - How do you start developing a high-performing marketing function? 

(33:38) - When does bringing on a fractional CMO make sense?

(35:24) - What's the best mix long-term for in-house marketing vs. outsourcing?

(37:36) - How do you find the right person to grow within your marketing function

(42:17) - What strategies do successful CEOs use to help get teams behind their vision?

(43:49) - What's really important to know about the Ideal Customer Profile?

(48:25) - How do you develop an effective outbound campaign?

(57:36) - How incoming CEOs can add value

From Episode 262 of Think Like an Owner. Watch the full episode here.

Today's episode is a rerun with past guest Ross Brendel, a co-founder and the managing partner of Westerly Group alongside cofounder Rich Littlehale. Westerly Group invests in acquisition entrepreneurs with committed, permanent capital to pursue a specific industry thesis over an indefinite time horizon. They are investors in several of our podcast guests such as Justin Vogt and Ed Redden, Eric Factor, and Austin King, among others.

I wanted to bring this episode back to your attention as permanent capital and longer time horizons are becoming more talked about today and I think it's important to discuss the nuances of this approach, as Ross does in this episode.

In this conversation, Ross shares Westerly's permanent capital thesis and model, whether buying a business has become harder or easier, how to think about a purchase price with a longer-term view, and the nuanced advantages of committed capital in pursuing acquisitions.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Ross on LinkedIn

Westerly Group

Sylmar Group

Era Services Group

Evermore Industries

Northrim Horizon

Business Model Generation

Topics:

(3:32) - Ross' background & career

(6:39) - Why do you think interest in longer-term hold vehicles has increased in the past few years?

(9:33) - Should entrepreneurs be less price-sensitive when looking to buy a business?

(11:36) - How do you find entrepreneurs with the right mindset when buying a business?

(13:42) - Do you think buying a business has gotten harder over the past 5-10 years?

(18:46) - What are some of the unique ways you've seen Searchers find companies to buy?

(20:25) - Can you tell us about some of the teams you've backed?

(23:19) - Can you talk through some of the advantages of committed capital structures?

(28:06) - Was it intentional to take a generalist approach to your work?

(31:53)- What happens if an entrepreneur you back loses desire for the industry they initially start Searching in?

(33:51) - Does your Zero Horizon Investor idea give you more flexibility in terms of the business models you go after?

(37:18) - Are there any other models in Search that are interesting to you?

(39:36) - How do you think you'll continue to find entrepreneurs and teams? Do you have a formulaic approach?

(42:10) - What college class would you teach if it could be about anything?

(44:12) - What's a strongly held belief you've changed your mind on?

(45:33) - What's the best business you've ever seen?

My guest on this episode is Sandy Paige. Sandy has been an operator several times over his career, including being a general manager at a Maine paper mill, a director of The Jackson Laboratory, and others which gave him a wide range of experience to use in growing the company he acquired as a searcher, Explora BioLabs.

He's also an outlier in being one of, if not the, oldest searchers. But his results speak for themselves: Sandy grew Explora BioLabs over the course of 4 years starting in May 2018 to sell for $295 million in April 2022.

Sandy and I talk about the importance of communication as a CEO and his philosophy behind it, how he sought and hired managers who could grow with the company, early career CEO mistakes to avoid, communicating with your board, and his priorities and focus in the CEO role.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Check out this podcast for a deeper dive into Sandy's background

The Jackson Laboratory 

Explora BioLabs

Sandy on LinkedIn

Topics:

(2:58) - Can you give us your background and career to this point?

(6:36) - How did the paper mill experience influence your management style?

(10:45) - What were some of the characteristics of bosses you worked for that you tried to emulate?

(12:43) - Are there skills that helped you refine your best qualities as a manager?

(15:30) - What do you look for when hiring?

(18:54) - What do you think early career CEOs often miss in management hires?

(21:56) - Are there questions or techniques you use to inform you the hire is a hard worker?

(24:14) - What started to happen after those hires?  

(27:41) - As your company grew, how did your team structures have to change?   

(33:45) - How do you position a company so that it increases enterprise value?

(35:39) - What made it so different for you?

(37:52) - Did you find it challenging to run the business while going through diligence?

(40:08) - What was your set of responsibilities and priorities as a CEO?

(42:03) - What kind of communication cadence did you have with your board?

(45:08) - How do you ask good questions to your board?

(46:34) - Is there any advice you often give to early career CEOs?

(48:21) - What strongly held belief have you changed your mind on?

(49:48) - What's the best business you've ever seen?

My guest on this episode is Michael Coscetta. Michael has held several high-level sales roles at companies like Square, Compass, his own company, and his current role as CRO of Paxos, and through it all has become an expert in designing and managing sales teams.

This was a fantastic conversation about all things sales and building sales teams and is one I will be re-listening to several times over the coming years. While a large portion of Michael's time has been spent in very large sales organizations, the principles he talks about are still widely applicable in companies of any size, and all regular listeners to this podcast are in for a treat.

Michael and I talk about writing high-value sales contracts, the growing importance of high-performing sales operations, how sales have become data-driven and more quantitative, how to recruit for sales, and the leadership of sales.

One final note before the episode, I want to meet more sales professionals, especially in data and data software. If you, or someone you know, have expertise in data enterprise sales I would love the chance to connect. You can find me on my website alexbridgeman.com, LinkedIn, and Twitter, or send me an email directly at alex.e.bridgeman@gmail.com. Thank you, I look forward to chatting soon!

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Paxos

Michael on LinkedIn

Superhuman's Fundraising Playbook with CEO Rahul Vohra on the Acquired Podcast

On Revenue Quality with Bradley Roofner and Logan Brown - Ep.145 of TLAO

Topics:

(4:32) - Michael's background and career

(7:03) - Are there any common principles you've picked up over the course of these vastly different experiences?

(9:28) - What have learned about building valuable sales contracts?

(12:42) - What processes or strategies have you developed to find the right pricing matrix arrangement?

(15:49) - Are there any questions you ask customers to find optimum pricing?

(18:55) - Have you seen an evolution in how sales teams are viewed in companies?

(22:04) - Is there any data set that has the most impact on a sales team?

(24:37) - What are the differences between sales orgs of less than 50 people and larger ones?

(27:33) - How do you go about setting sales goals?

(30:38) - Do you have a sense for trigger points for when you separate different parts of the sales process into their own individual teams 

(32:42) - How do you view renewals or upsells for existing customers vs. new ones?

(33:57) - What personalities or characteristics work best for filling out different sales roles? 

(40:31) - Are there any helpful questions or interview styles to determine whether a candidate is a good fit?

(42:57) - What are some best practices for making sure sales and products are communicating effectively?

(45:57) - Are there any communications methods that work well with customers?

(48:51) - How does the product team decide what customer feedback is valid and what is noise?

(53:09) - In this environment, how do you continue to build and improve your sales team?

(55:54) - Can you expand on the concept of the sales org being the brains of a revenue organization?

(58:00) - How can a CEO get more involved with their sales team in a non-disruptive way?

(1:00:16) - What strongly held belief have you changed your mind on?

(1:01:11) - What's the best business you've ever seen?

(1:04:06) - What other companies do you study and admire for their sales org?

My guest on this episode is Nick Buchanan. Nick and his father founded a data software business called BUCS Analytics in 2006. BUCS builds deep analytical dashboards for CEOs that pull from internal data sources like ERPs, inventory systems, and more. Long-time customer Trevor Flannigan, COO of the Flint Group, introduced us after hearing about my deep curiosity of data companies.

Nick and I talk about building the company with his father, building momentum in product development and sticking close to customers, hiring a talented team, and how to find groups and peers to help guide your entrepreneurial journey.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Nick on LinkedIn

BUCS analytics

Sean Joy – CEO Journey within Chenmark – Ep.152

Timestamps

(00:00:00) Intro

(00:02:15) What is Bucs Analytics and the founding story? 

(00:07:35) Are there any industries you've specialized in?

(00:09:38) Can you walk through product development?

(00:13:11) How do you decide on outcomes of experiments where results come out similar?

(00:16:25) Are there 2-3 ways you measure engagement and value? 

(00:17:41) What's been the process of evolution on the sales side? 

(00:20:53) What are the channels you're hoping to develop further?

(00:22:13) What are the benefits of having a group of peers over time? 

(00:25:34) Is there one change or development in your peer group that's helped the most? 

(00:27:35) Where was your mindset when starting Bucs and how has it changed over time?

(00:29:19) What are some of the most successful ways you've found to attract and keep talent at Bucs?

(00:32:21) What does it look like fulfilling a new employee's goals? 

(00:34:46) What've you learned the most about managing change in a company? 

(00:36:37) What's your philosophy for setting goals? 

(00:39:21) Have you ever made secondary adjustments to annual goals?

(00:40:30) What goal do you feel you're the most excited to achieve this year? 

(00:41:13) What strongly held belief have you changed your mind on?

(00:42:40) What's the best business you've ever seen?

My guest on this episode is Carl Streck, founder and CEO of MountainSeed, a data and software business serving commercial real estate professionals. I was introduced to Carl by Michael Arrieta after asking Michael for the most interesting entrepreneurs in data he knew of, and Carl's name was the first out of his mouth. Carl started MountainSeed in 2006 to build software serving banks making commercial real estate loans and eventually developed a data product to help banks make more data-driven decisions.

Carl and I talk about bootstrapping a data software company, evolutions in his management style as the company grew, the business models of data companies, and how staying close to customers impacted the development of their data product. Enjoy!

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Carl Streck on LinkedIn

MountainSeed

EOS

What Got You Here Won't Get You There by Marshall Goldsmith

YPO.org

The Economics of Data Businesses by Abraham Thomas

Craig Fuller on TLAO

Topics:

(2:46) - How has your thought process around raising capital changed over the years?

(5:43) - Does your mindset towards capital change when it comes to accelerating growth vs. starting growth?

(8:03) - What have you learned from peers or your own experience in finding the right investor/company fit?

(10:29) - What was your role and how did it evolve during different stages of team size in the organization?

(14:16) - As companies grow, where do you see CEOs and founders start to struggle?

(17:46) - Is there a way to build a culture that encourages feedback they might not want to share otherwise?

(21:05) - What are some of the most impactful behavioral changes you've made to build trust and feedback with the team?

(25:43) - When you study CEOs of larger companies, what is different about how they operate as leaders?

(28:23) - Can you walk us through how you view your product portfolio and how the two work together?

(32:40) -How do you compare SAAS businesses to Data Businesses?

(35:56) - Does your Data Analytics platform work within the platforms or software of customers?

(38:23) - How would you categorize the customers of your product?

(41:02) - Does the Analytics platform license 3rd party data sources?

(43:19) - How are you looking to design and build a data company that lasts?

(46:07) - How do you incorporate customer feedback or determine new features?

(49:09)- What's a strongly held belief you've changed your mind on?

(52:24) - What's the best business you've ever seen?

My guest on this episode is Sean Joy, CEO at Buccaneer Pirate and Southern Star Dolphin Cruise, a company owned by Chenmark in Destin, FL that provides seasonal boat tours. Sean was a part of Chenmark's GVP, the Generalist Vice President program that provides a career track to becoming a CEO at a Chenmark company.

Individuals start by working on a couple of projects within the portfolio, then take a non-CEO operating role in a company, before moving to a CEO role. Sean's background was in control workouts and restructuring, which we talk about to kick off the episode before he found a small business in Chenmark and inquired about their GVP program.

Over the course of the episode, we talk about Sean's finance experience, what he pays close attention to given his restructuring experience, managing cash in a highly seasonal business, the wide array of services offered on a tour boat and how they interact, and the power of price increases. Enjoy!

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Sean on LinkedIn

Southern Star Dolphin Cruise

Buccaneer Pirate Cruise

Chenmark

Topics:

(6:08) - What are some interesting lessons you learned and experiences in restructuring?

(12:52) - What are some habits you have today as a CEO that you can tie back to prior experiences in restructuring?

(14:40) - How did you connect with Chenmark and what about it was appealing to you?

(16:52) - What were the roles you had when you first joined the organization?

(20:27) - Were there any learning curves early on in your role as CEO?

(22:06) - How much debt was in the business?

(23:39) - What are some ways that you manage cash throughout the year with a heavily seasonal business?

(27:33) - What are some of the add-on services you've implemented to increase revenue?

(31:46) - What are your criteria for cutting vs. keeping products?

(32:47) - How much time and energy do you spend on pricing your products?

(38:10) - How dynamic is your pricing?

(39:28) - What other improvements are top of mind for you?

(46:26) - What strongly held belief have you changed your mind on?

(48:51) - What's the best business you've ever seen?

My guests on this episode are Heritage Holding co-founders Alex de Pfyffer and Ross Porter. Heritage acquires companies across industries, but has a special focus on IT services and data centers. I'm a data geek and love talking with entrepreneurs in data, and haven't talked with much of anyone on the hardware side so this conversation was a lot of fun for me.

We talk about identifying companies offering essential services, their data center acquisitions and strategy, what they've learned from private equity on growing companies, and thoughts on a long-term structure for Heritage going forward.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Heritage Holding

Alex de Pfyffer on LinkedIn

Ross Porter on LinkedIn

Topics:

(3:03) - What's the background for Heritage and how did you each get to this point?

(5:56) - What ideas were you considering for a startup?

(7:57) - Have there been any guiding principals or common threads through the acquisitions you've done thus far?

(11:49) - What does the data center business model look like?

(13:53) - Is there some overlap with your ISP or Fiber investments?

(15:00) - Is there some first mover advantage to bring Fiber Optic Cable to a certain area?

(16:33) - Who is your typical competitor?

(18:38) - Once you own an ISP, what are the ROI metrics for expanding that footprint?

(20:27) - Where do you see other opportunities in data for investments?

(26:10) - What have you learned from managing companies of different sizes?

(34:09) - What changes the most when you go from $10m to $50m of EBITDA?

(37:29) - What are some structure questions in your mind as you look to future acquisitions?

(43:35) - What's a strongly held belief you've each changed your mind on?

(49:41) - What's the best business you've ever seen?

My guests on this episode are Johnny Lieberman and Zack Miller, who together founded Worklyn Partners to acquire and grow cybersecurity and IT services companies.

A concept we talk a lot about in the episode is how the two businesses create a flywheel between each other. I find these flywheels fascinating and I've talked about others such as the flywheel between media and data with FreightWaves founder Craig Fuller in Episode 121.

Johnny and Zack share how the two business models function both together and independently, where growth is coming from and trends driving that growth, developing sales teams, and why only the paranoid survive. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Johnny Lieberman on LinkedIn

Zack Miller on LinkedIn

Worklyn Partners

Quadrant Information Security

Topics:

(2:41) - Can you walk us through the timeline of Worklyn and where you're at today?

(9:35) - How do your cybersecurity & IT platforms work collaboratively together?

(11:07) - Why are you pursuing growth via acquisition on the IT side but not in cybersecurity?

(17:07) - Is there a similar dynamic between sales in IT services and Cyber?

(18:08) - How does the sales cycle work from getting an IT customer over to the Cyber side?

(22:42) - What are some high-level industry tail winds you've observed?

(29:49) - Could the flywheel between Cyber and IT extend to software businesses or service tools that could support the business?

(33:59) - Within Worklyn, where do you see most of the value being created?

(36:49) - How have you been working to attract great people to your teams?

(40:01) - How have you structured management compensation?

My guest on this episode is Richard Reese. Richard took over as CEO of Iron Mountain, a physical records management business, in 1981. He ran the business as CEO through going public in 1996 before retiring from the role in 2013. Revenue over that period grew from around $3 million in 1981 to $3 billion in 2013.

Our discussion focuses on incentivizing teams with cash and stock, something Richard has thought deeply about over many decades, developing compensation plans, working with private and public investors, and a few stories from the early years of running Iron Mountain.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Richard on LinkedIn

Iron Mountain

Topics:

(4:03) - Richard's background, career, and time as CEO for Iron Mountain

(14:03) - What became easier when you went public? What became harder?

(17:30) - What did your management team look like when you stepped in and how did you look to evolve it?

(24:29) - When you started thinking about incentivizing the management team, what were some ways you got them to buy in?

(38:35) - What kind of challenges did you run into with equity compensations?

My guest on this episode is Judd Lorson. Judd acquired Alliance CAS, a specialty collection agency, in 2018 as CEO and in 2021 resigned from the role after a much more difficult road and path than he'd anticipated. Judd's story was recently profiled in a Yale paper by A.J. Wasserstein titled "The Judd Lorson Story" which we will link to in the show notes and I highly recommend reading for background on Judd's time as CEO.

For this conversation, we are focusing on new daily habits and foundations he has created influenced by his experience, what he values today, how those values have changed over time and the power of having a growth mindset.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

"The Judd Lorson Story" by A.J. Wasserstein

The Slight Edge by Jeff Olson

Judd on LinkedIn

Contact Judd via email at Judd.lorson@gmail.com

Topics:

(4:10) - Judd's background and career

(14:44) - What was a typical day or week like for you as a CEO and what would that ideally look like today?

(21:10) - How do you feel now in your emotional balance now vs. when you were working in the business?

(23:07) - Do you think if you had started your work as CEO with these habits it would've been a more successful experience?

(24:42) - How are you planning to adjust your work-life balance in a potential second stint as CEO?

(28:13) - What advice would you give to young searchers who are in the process of making life changes outside of work such as starting a family?

(31:30) - What are some tactics you could use to engage with those changing dynamics over time?

(33:32) - What goals did you have for 2022?

(38:06) - What are some of your Slight Edge Habits?

(41:55) - Are you totally caffeine free?

(44:06) - Was there anything to simulate day and night while on the submarine?

(47:04) - What other changes in your daily habits or values are you looking to achieve in the future?

(50:04) - Is there a strongly held belief you've changed your mind on?

(53:12) - What's the best business you've ever seen?

In this episode of Think Like an Owner, I sit down with Trey Bryson, an aviation industry veteran with deep experience across business aviation, commercial MRO, and aircraft completions. Trey shares how his career has spanned everything from customizing luxury VIP jets—including designing in-air hot tubs and modular gyms—to founding Jet Works, an independent MRO business.

We dive into:

• The major differences between commercial and business aviation maintenance
• How speed and efficiency drive profitability in aircraft operations
• The complexities of aircraft modifications, from dance floors to structural repairs
• Lessons learned from building and selling an MRO business through economic downturns

Trey also offers advice for ambitious CEOs, emphasizing the importance of financial strategy, team-building, and adapting to industry shifts. Whether you're in aviation or simply love hearing how businesses are built and scaled, this episode is packed with insights, stories, and hard-earned wisdom.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Aviation Technical Services

Trey on LinkedIn

Topics:

(00:00:00) - Intro

(00:02:18) - Trey's Career Journey in Aviation

(00:03:47) - Differences Between Business and Commercial Aviation

(00:06:02) - Unique Requests in Aircraft Interiors + Challenges and Innovations in Aircraft Maintenance

(00:36:57) - The Impact of Economic Downturn on Business Aviation

(00:46:25) - Advice for Ambitious CEOs

(00:47:34) - Conclusion

My guest on this episode is Luis Reyes, managing partner at Iberian Ventures in Spain. Luis worked in strategy consulting before acquiring small companies in Spain in a similar vein as the search fund model through Iberian. We kick off by talking about the buyout market in Spain and what makes it particularly attractive. For example, all private companies in Spain have to file their financials with the government. As a result, the full financial picture of any company in Spain can be found and sorted.

We also spend a great deal of time talking about one of their core investment theses, the fire protection market, and why it's an ideal market for consolidation.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Luis on LinkedIn

Iberian Ventures

Topics:

(3:42) - What is Spain like as a buyout market?

(9:05) - What are the regulations around requiring private companies to make their financials public?

(12:17) - Did you have any previous ties to Spain before deciding to plant roots there?

(13:52) - Was your previous career experience in finance and consulting helpful in working with business owners?

(15:12) - Can you give us a walkthrough of the companies you've purchased so far and how you structure acquisition?

(18:32) - What does the fire protection industry look like country-wide and how does it compare to how you've approached it?

(25:00) - What are financing options for acquisitions?

(26:33) - Can you walk us through an example of a transaction and integration?

(32:18) - What are your options for exiting?

(34:38) - What are the options or paths you're thinking about in the long-term?

(36:07) - Do you see other Searchers in Spain stepping outside the traditional model?

(38:09) - What other industries do you find interesting and is there any limit to your team's capabilities to manage over multiple industries? 

(42:13) - Are you raising money to build internal software?

(45:25) - What's a strongly held belief you've changed your mind on?

My guests on this episode are Bradley Roofner and Logan Brown, who together, along with a third partner Kade Thomas, acquired WLE, a landscaping firm in Austin, Texas, in 2017. After nearly four years of operating, they sold the company to Brightview, a public landscaping company and one of the largest in the country.

Our discussion today focuses on revenue quality, a topic Bradley and Logan have given a great deal of thought to. We talk about defining revenue quality and how to identify high and low quality revenue, creating your ideal customer profile, how to sell that customer building a motivated sales organization, emphasizing high quality revenue across an organization, writing more valuable customer contracts, and various tips they have for CEOs looking to boost revenue quality and thereby their company's valuation. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Bradley on LinkedIn

Logan on LinkedIn

The E-Myth by Michael Gerber

Topics:

(2:44) - What was the business you ran in Austin?

(4:29) - What would you say are some aspects of high-quality revenue and aspects of low-quality revenue?

(6:57) - Was there any revenue that wasn't as clear cut to be either high or low quality?

(8:35) - How did you beef up the quality of revenue in your first 90 days?

(15:350 - How did you go about determining who your ideal customer would be?

(19:38) - What decisions are made based on the ideal customer profile?

(28:09) - How did you build out your outside Sales Org?

(31:31) - Did you have more success hiring people for Sales that had industry experience or Sales experience?

(33:15) - How did you instruct Sales people to navigate price increases?

(35:01) - Was your Sales Team compensated based on margin?

(36:07) - What were some levers in cash and collections that improved Quality of Revenue?

(44:04) - Did you find that as Quality of Revenue increased, the number of customers in collections decreased?

(46:40) - Did you find some interaction between construction and maintenance?

(50:47) - How did you go about measuring the conversion rate from low to high quality revenue?

(53:11) - How did Quality of Revenue impact your lives?

(59:11) - What advice would you offer CEO's looking to do general clean up in their business?

My guest on this episode is Josh Schultz, current president CaneKast and previously co-founder of the Chess Group. Josh has partnered with Reg Zeller, a former podcast guest from Episode 81 and CaneKast founder, to acquire and streamline foundries across the country. But as Josh and I talked about in the episode, that is far from their only ambition.

Josh and I talk about what has changed the most in the year since joining CaneKast, how he approaches scaling, organizations, and teams, documenting processes, change management, and finding a complementary partner to work with.

Josh is also a great friend and a person I deeply admire. He's incredibly intelligent, process driven, and creative, and I always love talking with him. Please enjoy our conversation.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Josh on Twitter

JoshuaSchultz.com

CaneKast

Reg Zeller on Twitter

The SMB Ops show

Topics:

(2:58) - What would you say are the biggest changes you've seen in your business in the past 10 months?

(4:45) - Do you feel like there's an order of operations for changing or tracking different things?

(7:00) - How did you go about understanding pricing and mold counts?

(10:47) - Do you believe you're creating a competitive advantage beyond pricing that contributes to growing sales?

(12:40) - What's the most challenging piece to improving service?

(14:45) - How much do you think making internal data more transparent has impacted your efforts?

(19:46) - How do you get someone with deep domain expertise to share and document knowledge?

(20:51) - What is the goal for building multiple solo companies within CaneKast?

(23:42) - What are some business models that are inspiring this move?

(25:05) - The importance of building a competitive advantage

(27:15) - Do you feel your competitive advantage will allow you to acquire other foundries?

(29:02) - Do you think there's correct pacing to change?

(30:45) - How do you approach setting a vision for the company?

(34:49) - How do you view what types of aspects of the business will change next?

(36:51) - Where do you think you'll feel the strain as you start acquiring companies?

(38:34) - How do you go about learning a new topic?

(42:10) - How have you used media and podcasting to build relationships?

(43:47) - What advice do you have for finding a good partner?

(46:00) - How did you think about your role at CaneKast?

(48:18) - Have you always had this Entrepreneurial Impatience?

(50:43) - Where do you feel like you need to be patient?

(54:56) - Evolving the CEO role to pure people & executive team management

(59:26) - What's a strongly held belief you've changed your mind on?

(1:00:09) - What's the best business you've ever seen?

(1:03:24) - What's next for you in manufacturing after foundries?

My guest on this episode is Brandon Kuchta, the former CEO of Analytical Technologies Group, which provides repair, maintenance, and contract services for lab instruments. I say former because he sold ATG last October, and today's episode is going to cover all things selling a company from determining the right timing, what is typical in a process, and communication across stakeholders. We also talk about life after the sale, including Brandon's consulting period with the new owners and how operators can relax and give themselves a well-deserved and often much-needed break. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Brandon Kuchta on LinkedIn

Seven Springs Partners

Topics:

(2:31) - What was the business you ran and what was the process for selling it?

(4:09) - How did you know it was the right time to sell the business?

(7:03) - What advice did you get from other folks about selling a business and planning for life after the sale?

(8:27) - How long was it between deciding to sell and selling the business? 

(9:25) - What sorts of things would you do to prepare to sell a business if you had a 2-3 year runway?

(13:12) - Would you run a business differently if you knew you would be selling it?

(14:39) - What made you decide to hire a bank to represent the company instead of going directly to buyers?

(16:18) - How did you filter which bank you would partner with?

(19:41) - What types of offers were you fielding?

(22:11) - What were the typical terms you saw for seller financing?

(23:38) - How did you think through rollover structures within offers?

(26:04) - What were some expectations buyers had if they wanted you to roll over some equity?

(27:48) - What was your thinking on a strategic sale vs. a PE sale?

(29:33) - How do you think about communicating the process of selling with different stakeholders?

(34:28) - What was the reaction from your team when you announced the sale?

(36:32) - What did the consulting agreement look like?

(38:41) - What is your role today?

(39:16) - How have you relaxed and decompressed as the former CEO?

(43:31) - What are your health and fitness plans?

(49:10) - What's a strongly held belief you've changed your mind on?

(50:59) - What's the best business you've ever seen?

My guest on this episode is A.J. Wasserstein. Early in his career, A.J. founded Archives One, a physical records management business he operated as CEO for 17 years before selling to Iron Mountain. He then acquired One Source Water, which was eventually sold to Water Logic in 2016. He then began teaching at Yale School of Management where he has written ad nauseam about nearly every topic within growing and running small companies and search funds. His writings are my go-to resource for many questions and business concepts I want to learn more about, and I'm quick to recommend them to others.

A.J. and I talk about being a professor and how to get involved if you'd like to teach, why students do not pursue entrepreneurship through acquisition and work-life integration as CEO, a topic A.J. has written and thought very deeply about, among other topics. Please enjoy this fantastic conversation with AJ Wasserstein.

Links:

More on A.J. Wasserstein

The Judd Lorson story by A.J. Wasserstein

Why MBA Students Do Not Pursue Entrepreneurship through Acquisition by A.J. Wasserstein

How CEOs actually spend their time? by A.J. Wasserstein

Topics:

(3:14) - What made you excited to publish a paper covering an unsuccessful search?

(4:26) - Is it a conscious part of your process to present both sides of an issue in your writing?

(5:45) - What was your experience like going from a CEO to academia?

(8:39) - What were some challenges you faced as a CEO?

(13:49) - In your experience, did you find your workload felt reduced as you grew different departments?

(15:20) - Is work-life integration as a CEO possible?

(18:03) - Are there any CEOs you know who have achieved this balance?

(19:39) - How do you think about the ROI of your time spent as an investor, professor, and content creator via research papers?

(25:52) - You said it takes 5 years to be a successful CEO, would you say it takes the same amount of time as a professor?

(27:04) - What are some best practices for being an effective professor?

(30:20) - What moments as a professor bring you the most joy?

(32:02) - How do you help students think by asking them questions?

(34:25) - For someone in the process of selling their business, how would you recommend testing out the waters of academia?

(37:59) - What were some interesting observations you saw in students after they went through the Search Fund curriculum? 

(43:20) - For students wanting to pursue Search, what roles were most effective in helping them feel ready

(48:41) - Do you have any desire to turn your papers into a book one day?

(49:55) - Do you find there are any themes that come up consistently in your writing?

(52:15) - Do you get the sense more folks are thinking about work-life integration than ever before?

(55:18) - What strongly held belief have you changed your mind on?

(57:42) - What's the best business you've ever seen?

My guest on this episode is Jamie Shah. Jamie worked in investment banking and Google before returning to her family's business, Chem-Impex International, which manufactures materials for life sciences companies, as VP of Operations.

Today, she is the managing director at the company and a professor at Chicago Booth, where she teaches a course on family business. Our discussion focuses on lessons to be learned from family businesses, which are more trusted and stable and generate higher returns. We talk about what success looks like in failing businesses, the balance of paradoxes, and how to apply principles that make family businesses successful to all companies.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Connect with Jamie

HeartlandHopeMission.org/Christmas

Jamie on LinkedIn

Chem-Impex International

Kauffman Fellows

Lee Kum Kee

Family Business as a Paradox by Amy Schuman, John Ward, and Stacy Stutz

Unconventional Wisdom by John Ward

Succeeding Generations by Ivan Lansberg

The Three-Circle Model

HBR: What You Can Learn From Family Business

The Five Dysfunctions of a Team by Patrick Lencioni

Topics:

(2:46) - Jamie's background and career with Family Businesses

(9:46) - How do you feel like your family's business is run compared to others?

(11:12) - What was the most interesting Family Business you learned about at Northwestern?

(13:24) - Why do you think there are such high levels of stability, trust, and returns in Family Businesses?

(15:54) - The boring aspect of Family Businesses

(18:53) - What are some observations you have about the different paths within entrepreneurship?

(22:01) - What are some examples of different business goals within Family Businesses you've studied?

(25:00) - What are some paradoxes you've identified in Family Businesses?

(28:38) - How does your Family Business deal with being uncomfortable in these paradoxes?

(30:16) - Do you think conflict is good because it forces clarity?

(31:20) - Which benefits of a Family Business would be most replicable to other styles of businesses? Which would be most difficult?

(34:29) - Why are Family Businesses cautious to take on debt?

(38:35) - How often is the CEO of a Family Business a member of the family?

(40:44) - How do Family Businesses navigate liquidity, control and capital?

(42:24) - What strongly held belief have you changed your mind on?

(43:39) - What's the best business you've ever seen?

My guest on this episode is Nevin Raj, Co-Founder and COO of Grata. Grata is a fascinating data software business that takes in all available public information about private companies, such as their website, LinkedIn, funding data, PPP data, and so much more. It then uses that data to create the most accurate profile of that company in their industry, headcount, business model, revenue range, and more.

Nevin and I talk about the categories of data businesses and where he sees data businesses evolving into, how to accurately estimate the revenue of private companies and how the best investors do it today, and how to build a data software business.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Nevin Raj on LinkedIn

Grata

Politico Pro

Quorum

Verisk

Second Measure Transaction Data

Economics of Data Businesses by Abraham Thomas

Topics:

(3:12) - What are your thoughts on data vs. workflow as business models?

(7:30) - Do you see data businesses developing into more of a 'wisdom' category of companies?

(13:42) - Can you walk us through the different types of data businesses?

(22:53) - How would you describe a workflow company?

(24:37) - Within your business, can you walk through the different ways you can get data from private companies?

(27:52) - What are some of the data sets that correlate most with revenue size?

(30:04) - How do the leading investors you've studied or worked with historically estimate the size of a company?

(32:14) - How much do you balance measurable data and intuition?

(34:51) - How do you integrate the data you have with your client's software and workflows?

(38:11) - What were the early days of Grata like and what did growth look like?

(41:27) - What second-level data sets do you want to add to Grata over time to build a moat?

(44:13) - Do you think eventually most data businesses will become workflow businesses?

(46:49) - What's a strongly held belief you've changed your mind on?

(49:18) - What's the best business you've ever seen?

(50:56) - Are there any insights you've gleaned from ZoomInfo you want to apply to Grata?

I'm very excited to share that starting today Think Like An Owner will now be publishing episodes twice per week. This change coincides with our decision to close the Operators Handbook and move those topic-specific conversations to the podcast for Thursday morning episodes. You can expect these episodes to focus on topics like sales, culture, hiring, debt, capital allocation, leadership, board meetings, and dozens of other topics. This is an addition I've wanted to make for a long time, and I finally feel like the podcast is ready to go to this next level towards our endless pursuit of better in small business.

The second episode also means we have more availability to partner with great companies serving operators and investors through podcast sponsorships. If you're interested, please send me an email at alex@jointheoperator.com or connect with me on Twitter or our website alexbridgeman.com. I'd love to chat.

Jessica Markowitz, President and COO at Paragon Legal, kicks off our new topic-specific episodes. Paragon offers outsourced legal services to corporate legal departments, which Jessica and her partner Trista Angele acquired in 2018. Our conversation covers all things culture, including defining culture, maintaining and enforcing culture, and how to build a culture in a remote-first company. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Links:

Jessica Markowitz on LinkedIn

Paragon Legal 

Topics:

(2:58) - What is the purpose of Paragon Legal?

(5:10) - What values do you view as incomplete and what are some complete ones?

(9:47) - Is there one value that you see as most difficult to live out?

(11:55) - What are some of the most recent adjustments you've made to Paragon's values?

(13:31) - How do you sus out whether someone will live out your values in the interviewing and onboarding process?

(16:42) - Do you have some way to quantify an employee's alignment with values during performance reviews?

(17:54) - How do you maintain and communicate values to the team?

(19:33) - Have there been any particular challenges with enforcing values?

(23:03) - How have you approached building a culture in a remote-natured company?

(29:07) - What are you considering adding or changing concerning communication or trust building?

(30:20) - How do you approach a situation where a team member is continuously not living up to the Paragon values?

(31:59) - What are some other benefits you've seen from focusing so much on values and culture?

(34:04) - Have you found any way to accelerate the process of building trust with a new employee to be open and honest with management?

(37:38) - Do you view the act of building a strong culture allows you to trust your team much easier in terms of delegation?

(39:30) - Where are you focusing on improving right now in terms of culture?

(43:05) - Do you have a strongly held belief you've changed your mind on?

(44:02) - What's the best business you've ever seen?

My guest on this episode is Trevor Flanagan, COO of Flint Group, a home services roll-up founded by Collin Hathaway. Collin's appeared on this podcast twice, on episodes 32 and 90, for good reason, and I highly recommend listening to those episodes as a primer for this conversation with Trevor. Trevor has a fascinating background as I'll touch on earlier in this episode. He started his career as a district manager for Aldi before becoming GM of Bob Hamilton, a home services business in Kansas City.

He then left and co-founded Professional Chats, which offers website chat software to home services businesses, before selling it two years later. In those two years, he and his co-founder grew it from 3 to 150 employees and nearly $10 million in revenue. Soon after selling, he met Collin and joined Flint.

Our conversation covers how great companies scale, how crucial of a role sales and hiring play in scaling, the role of debt, and everything in between. Like Collin, Trevor has an amazing ability to make hard problems simple and teach through storytelling and I'm positive you'll enjoy hearing his story. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Trevor on LinkedIn

Flint Group

Predictable Revenue by Aaron Ross

Episodes 32 & 90 with Colin Hathaway

Topics:

(3:40) - What's your career been like scaling companies across different industries?

(10:24) - How were you able to land a job managing a grocer at only 22?

(14:27) - What was the most common issue these different Aldi locations were struggling with?

(16:54) - How did you set up systems when you co-founded your first company?

(23:23) - Where did your growth in the first 18 months come from?

(26:13) - How did you eventually get to Flint?

(28:55) - What's scaling been like at the PE level?

(31:07) - Of the companies, you've seen, is there a consistent theme as to why they don't scale?

(33:21) - How do you adjust cultures as quickly as possible without breaking things?

(34:37) - How do you figure out what KPIs are most important for certain roles?

(35:54) - Once you have established a culture and KPIs, what's next to accomplish to scale?

(38:00) - Do you have a case study example of a formula that works for scaling?

(40:29) - Do you hire first before tackling marketing?

(42:44) - What are some of the most challenging parts of the sales side of these businesses?

(47:57) - How do you identify potential Salespeople and how do you design the training process?

(49:27) - What's your philosophy for compensation and incentivizing Salespeople?

(50:51) - What're your thoughts on scaling in terms of cash flow?

(53:43) - What other impediments to scaling are top of mind for you day to day?

(55:15) - What are you most excited about for Flint over the next 2 years?

(56:05) - What's a strongly held belief you've changed your mind on?

(57:25) - What characteristics of folks make them desirable to work for?

(1:00:10) - What's the best business you've ever seen?

My guests on this episode are Paul Yanchich and Ryan Beaver. Paul is a co-founder of Arcadea Group, a vertical market software holding company that Paul and his co-founder Daniel raised $320 million to found 14 months ago. In this episode, Paul is joined by Ryan who serves as managing director of value creation and operations.

Our conversation acts as a part two to our first episode with Paul and Daniel, episode 84, and breaks down learnings from 14 months of activity, lessons learned, where software acquisitions see the most improvement partnering with Arcadea, and evaluating management teams for the long haul. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Arcadea Group

Paul Yancich On LinkedIn

Ryan Beaver on LinkedIn

Episode 84 on TLAO with Paul Yancich and Daniel Eisen

The Outsiders by Will Thorndike

Topics:

(3:04) - What have been some early learnings as first-time investors and founders?

(5:50) - In what ways are you efficient with Arcadea and where do you focus your resources?

(9:42) - What do the first 1-2 years look like after closing?

(16:38) - What are some other ways you create value and make it collaborative with CEOs that join you?

(20:53) - What parts of a software business have changed and what's stayed relatively the same?

(24:46) - When you look at software companies today, what are the most common technical best practices missing?

(30:56) - What are some key learnings you've had from chatting with folks like Will Thorndike and Mitch Rails?

(37:47) - What makes founders excited about Arcadea over other potential acquirers?

(40:04) - Do you have any ambition to be a public company?

In this episode of Think Like an Owner, I sit down with Eric Legvold and Trey Darr of Davinci Jets to explore the business of private aviation management and MRO (Maintenance, Repair, and Overhaul) services. We dive into how Davinci Jets was built from the ground up, the evolution of private jet management, and why the company has remained profitable every year since its founding.

Eric shares how the company pivoted from its original single-seat charter concept to full-service aircraft management, bootstrapping the business while maintaining a lean and disciplined approach to growth. Trey brings insights from his experience in aircraft maintenance and explains how Davinci is balancing fleet management with third-party MRO services, ensuring efficiency while expanding their customer base.

We also discuss:

• Why more Fortune 500 companies are turning to third-party flight management
• How vertical integration in aviation can reduce costs and increase control
• The challenges of hiring and scaling in the MRO industry
• How Davinci has stayed profitable in an industry where many companies struggle

If you're interested in private aviation, business strategy, or the complexities of running a capital-intensive operation, this episode is full of insights from two experienced operators navigating an evolving industry.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. 

Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/

Links:

Davinci Jets

Trey Darr on LinkedIn

Eric Legvold on LinkedIn

Topics:

(00:00:00) - Intro

(00:03:58) - Starting Davinci Jets

(00:09:09) - Growth constraints

(00:11:44) - Ventures before Davinci

(00:13:46) - The upside to MRO

(00:17:31) - Prioritizing your own fleet vs. external customers

(00:18:28) - Growth plans

(00:20:56) - MRO & Management compliments

(00:22;59) - What do you do differently to maintain profitability?

(00:27:16) - The Charlotte market

(00:29:22) - MRO Growth

(00:31:46) - Process improvements

(00:33:30) - Market growth

(00:40:29) - The slowdown in Jet Cards

(00:43:35) - What are you most excited about in the industry?

My guest on this episode is Juan Ruiz. Juan is the founder of CommunEtA, the first-ever student-led search investment fund. The goal of the fund is multifold: provide exposure and training for students wanting to build a career in search, provide a grassroots investment option for searchers, and spread the word about search across the country.

We start off the episode discussing a few student-run funds on the venture capital side that inspired CommunEtA and round out the conversation with topics like building a team of students that are constantly joining and graduating, the power of search to transform someone's career, and how search might evolve in the future. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Juan Ruiz on LinkedIn

Entrepreneurship Through Acquisition Student Club

Blue Road Capital

Severance on Apple+

Topics:

(3:32) - What models did you study for this dorm room-style fund for the VC world?

(6:52) - What kind of oversight is there from the University staff?

(8:15) - What's the process for creating systems around the fund given the high turnover of graduating students?

(10:07) - What was the inspiration for the fund and the mission, vision, and value behind it?

(13:36) - What was your background prior to your MBA at Harvard?

(18:40) - What's the interest level you're seeing from students toward Search Fund Investing?

(21:50) - What do you view as the main goal of the fund?

(26:53) - What's the involvement of students in the fundraising process?

(27:46) - What will your role be for Commune ETA going forward?

(29:06) - What are some roles and jobs for students in the Club?

(30:24) - Is there any conflict of interest with students helping to run a Fund while also pursuing Search?

(32:08) - Do you plan to expand this club to other MBA programs?

(33:22) - If this club was in 5 schools, what would the investment committee look like?

(35:08) - Do students get paid?

(35:25) - What are some of the different compensation models you look at?

(35:55) - What challenges do you foresee with growing this club across other universities?

(36:55) - How many students do you need to have quality output?

(37:59) - Evangelizing Search

(42:26) - What college class would you teach if it could be on anything?

(44:43) - What strongly held belief have you changed your mind on?

(46:52) - What's the best business you've ever seen?

My guest on this episode is Alexis Grant. Alexis and I have gotten to know each other through our mutual interest in media and our two small but growing media companies. We share thoughts, ideas, and advice back and forth all the time, and I'm excited to finally record one of our conversations.

Alexis founded a blog management company that was acquired by The Penny Hoarder, which then sold and gave her some starting capital for The Write Life, which she ran for a few years before selling that business too. Now she's founded They Got Acquired, a media business covering small online business exits with a growing newsletter and data product.

We discuss all things teams, products, creating content, and one of my obsessions: the convergence of media and high-end products like data. Please enjoy this wonderful episode with Alexis Grant.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Links:

Alexis on LinkedIn

They Got Acquired

The Penny Hoarder 

AirTable

The Hustle

Ben Collins Google Sheets Training

StyleBot.app

Topics:

(3:46) - Alexis' career journey

(8:52) - Why do you think 'They Got Acquired' would be a more interesting business to run?

(9:40) - What issues did you run into in previous roles?

(11:01) - What is They Got Acquired?

(14:16) - How have you approached building your team?

(16:18) - How do you determine what tasks you'll work on vs. delegating to the team?

(18:40) - Do you try to focus on revenue-generating tasks over content or operations-related tasks?

(20:17) - What next task are you looking to delegate?

(23:41) - What role will you fill for your first full-time hire?

(24:28) - What would a full-time writer be able to accomplish that you can't right now?

(26:04) - Is the research team for the database different than the writing team?

(27:14) - How do you ensure the media and date sides of the business interact with each other?

(30:04) - Are there any companies you find interesting that have a media arm alongside a high-end product?

(32:40) - Have you seen a media business buying a company that sells products best suited for its audience?

(36:05) - Have you thought about an event strategy at some point?

(37:05) - How do you think about competition in your space?

(41:52) - How do you balance what you want to do with your business vs. customer feedback?

(42:21) - What are you most excited about over the next 24 months?

(43:04) - What college course would you teach if it could be about anything?

(43:43) - What's a strongly held belief you've changed your mind on?

(46:37) - What's the best business you've ever seen?

My guests on this episode are Kurt Leedy and Kyle Coots, co-founders and managing directors at Miramar Equity Partners. Kurt and Kyle have an interesting vantage point in the search world being backed by a family office with an agnostic time horizon, allowing them to invest in the widest set of opportunities in search and parallel spaces.

Our episode focuses on a concept they developed they call the three ways to make money, those being classic LBO, M&A-driven strategies, and organic growth. We dive into the characteristics of each along with a few examples from their portfolio.

We also touch on how the intersection of two or more methods can create exponential outcomes. Finally, we discuss a few theses they find interesting in healthcare and software and how they develop a thesis on an industry.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.

Special thanks to our sponsor: Oakbourne Advisors

Links:

Miramar Equity Partners

Kurt Leedy on LinkedIn

Kyle Coots on LinkedIn

Will Thorndike with Patrick O'Shaughnessy

BPD Zenith

Flint Group

Swoogo

Encore Infusion

Constellation

Business Breakdowns - The NFL

Time Codes:

(3:36) - How did your backgrounds help form this concept of "The three methods to make money"?

(9:18) - Do you have a model of investing that resonates most with what you're looking to accomplish?

(12:24) - Have Search CEO's been primarily focused on one of these three buckets in your experience?

(15:51) - What are some characteristics & examples you've seen of the Classic LBO investing model?

(18:36)- What questions or risks are you optimizing for when considering LBO?

(22:13) - What are some factors that have correlated with a high retention rate in companies you've observed?

(24:23) - Can you walk us through how you divide M&A Driven Strategies into its two subcategories: Roll-Up and Transformative?

(33:46) - Is there some value in having M&A experience for a CEO & their company?

(35:42) - Why do you think there is such increased popularity in the M&A strategy within Search?

(39:00) - Which companies and characteristics fall under the Organic Growth Model?

(46:00) - What are some examples of companies who have combined these methods and found success?

(51:10) - What are your thoughts on Software businesses and any opportunities in that space?

(54:40) - What are some ways you develop and validate different theses?

(1:01:19) - What strongly held belief have you changed your mind on?

(1:03:32) - What's the best business you've ever seen?