How to grow a premium service business through trust, referrals, and client retention.
For founders and operators building high-touch services and trying to scale without paid acquisition.

Leigh Rowan, founder and CEO of Savanti Travel, joins Jason Shafton to break down how he built a luxury travel management company serving ultra high net worth individuals, family offices, VC firms, and Hollywood entertainers without ever advertising. He explains how Savanti evolved from helping entrepreneurs unlock value from points and miles into a full-service travel business built around 24-7 support, personalization, and relationships. The conversation covers how his team uses CRM workflows, SOPs, and regular standups to deliver consistent service across five continents, how they ask for referrals after delivering concrete wins, and why they have fired clients worth as much as 25% of revenue to protect the team and the business. Leigh also shares that Savanti has saved clients more than $10 million by using points and miles more strategically.

• Why Savanti chose word of mouth over paid advertising and how that shaped client selection
• How the team uses monday.com, SOPs, standups, and shared context to deliver high-touch service at scale
• Why most people leave points and miles value unused and how Savanti turns those assets into real savings and better experiences
• How Leigh thinks about referrals, client feedback, hiring for judgment, and protecting culture even when revenue is at stake

Timestamps from transcript

• 00:00 — What luxury travel management actually means
• 03:22 — From points and miles to full-service travel support
• 07:26 — The system behind saving clients money with loyalty assets
• 11:42 — Why Savanti never advertised and how word of mouth compounds
• 17:37 — Handling travel crises, hiring for judgment, and firing bad-fit clients
• 21:05 — Client feedback, luxury as personalization, and how to grow by word of mouth

Guest
Leigh Rowan — Founder & CEO, Savanti Travel
Website

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

How to acquire a profitable SaaS with minimal upfront capital.
For operators considering ownership but hesitant to start from scratch.

Doug Breaker, CEO of Shoeboxed and former CEO of MD Hearing Aid, explains why he chose to buy a 20-year-old SaaS company instead of building one. After running an eight-figure DTC business, he acquired Shoeboxed using an SBA loan with only 5% down. He breaks down how he sourced deals, structured financing, evaluated distribution over tech, and identified upside in an under-marketed business with a million-person email list. The conversation covers the actual mechanics of SBA loans, due diligence priorities, and what it takes to stabilize and grow an acquired SaaS in the first 90 days.

• How SBA loans work for SaaS acquisitions and how he structured a 5% down deal
• Why distribution, customer base, and cash flow mattered more than the product itself
• Common mistakes operators make when evaluating build vs. buy decisions
• How to approach your first acquisition and test interest before committing full-time

• 00:00 — Why buying a SaaS beats building from scratch
• 02:01 — From CEO-for-hire to buying Shoeboxed
• 03:51 — How he sourced and evaluated acquisition opportunities
• 04:41 — How SBA loans and deal structure actually work
• 06:47 — First 90 days after acquiring a SaaS
• 10:25 — Growth lessons and how to approach your first acquisition

Guest
Doug Breaker — CEO, Shoeboxed
Website
LinkedIn

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

Episode #204: John Kennelly — Founders who hate sales still have to sell

If sales feels intrusive, this episode reframes it as problem-solving.
Built for founders avoiding sales calls, decks, and outreach.

John Kennelly, Founder of I Hate Sales, works with founders who have never had a sales job and actively avoid selling. In this episode, he explains why sales fear is usually a mindset problem, not a skill gap, and why curiosity matters more than persuasion. The conversation covers running discovery without pitching, qualifying people out quickly, and why early founders slow themselves down by building systems instead of talking to customers. Kennelly shares concrete examples from his cohort work, including starting with interviews instead of sales calls and what to track before using a CRM.

What you’ll hear

• Reframing sales from “intrusion” to helping through discovery
• How to run interviews instead of sales calls
• Why broad ICPs, decks, and CRMs backfire early
• The only two metrics to track before you have customers

Chapters

Chapters with timestamps

• 00:00 — Why founders dread sales
• 02:17 — Sales as helping, not intruding
• 03:39 — Curiosity and discovery before pitching
• 05:17 — Qualifying hard and knowing your ICP
• 08:16 — Interviews instead of sales calls
• 13:48 — What to track before using a CRM

Links & resources

GuestJohn Kennelly — Founder, I Hate Sales
Website
LinkedIn

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois
• Subscribe / Follow Jason

How founders use acquisitions to grow without betting the company.
For operators considering their first inorganic deal.

Trevor Houghton is CEO of Pass Galleries and a former private equity and corporate development operator. He breaks down how founders can use acquisitions to increase enterprise value without overextending capital. The conversation covers how deals actually get sourced, why most failed acquisitions start with the wrong premise, and how Trevor structures transactions using debt, seller notes, and earn-outs to reduce downside. He walks through a concrete example of acquiring $5M in EBITDA with no net cash outlay and explains why integration planning must start before the deal closes.

• Why the best acquisitions start as partnerships, not cold offers
• The customers vs. capabilities rule and why you must only extend one
• How no-money-down deals work using debt and deferred payments
• Why day-one integration and early culture alignment determine outcomes

Timestamps derived from the episode transcript.

• 00:00 — Structuring acquisitions with minimal cash risk
• 00:30 — Introduction to inorganic growth and Trevor’s background
• 01:44 — Building acquisition paths through partnerships
• 03:13 — The customer vs. capability decision framework
• 04:07 — Identifying targets through existing customer usage
• 05:03 — Growing earnings and valuation through acquisitions
• 06:04 — Integration planning before close
• 06:29 — Culture integration and no-money-down deal mechanics
• 08:05 — Building an acquisition engine

Guest
Trevor Houghton — CEO, Pass Galleries
https://www.linkedin.com/in/trevor-houghton-th/

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

John Connolly - Make your growth story hold up in investor diligence

How to present growth so it is defensible, measurable, and scalable.For founders raising and operators building board-ready growth reporting.

John Connolly is a Managing Director at Spectrum Equity, and he explains what he expects to see when a company tells a growth story at the growth equity stage. He covers why founders often stop at simplified metrics instead of going deep on channels, cohorts, and what is actually repeatable. John breaks down two common issues he sees in diligence: when each incremental dollar stops working, and when teams blend organic and paid in a way that hides what is driving performance. He also shares Spectrum’s framing for evaluation: identify what makes the company special, then isolate the few growth drivers that truly move the business.

What you’ll hear

• ​How Spectrum pressure-tests whether growth is durable, not just up and to the right
• ​How to separate organic and paid so you can explain what is really working
• ​What breaks when incremental spend hits diminishing returns, and why teams miss it
• ​A practical way to focus your story: the “special thing” plus a short list of real growth drivers

Chapters

• ​00:35 - Intro: what investors diligence in a growth story
• ​02:48 - The common miss: not going deep enough on growth
• ​03:43 - Diligence issues: incremental dollars stop working, blending organic and paid
• ​05:08 - Compounding advantages and creator-led organic loops
• ​06:36 - Evaluation framework: what is special, then what actually drives growth
• ​08:29 - Why pace of execution matters in fast-moving AI markets

Links & resources

Guest

John Connolly — Managing Director, Spectrum Equity

spectrumequity.com

LinkedIn

Mentioned

Otter

Kajabi

Teachers Pay Teachers

About Frank Growth

Frank Growth is a podcast about how companies actually grow - real operators, real constraints, real decisions.Hosted by Jason Shafton.

Promotional links

• ​Work with Winston Francois: https://wf.team/podcast
• ​Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

Episode #201: Cait Anderson — Building trust into a repeatable growth system

Trust breaks faster than funnels.
This episode is for operators trying to make growth predictable without killing speed.

Cait Anderson is Chief Marketing Officer at Winston Francois. In this conversation, she and Jason unpack what actually makes a growth system sustainable: predictable returns, clear operating rhythm, and trust that compounds instead of resets. They walk through concrete examples, including a B2B SaaS company spending $1M/month in paid media, how experimentation budgets are set at different stages, and why breaking a product promise can wipe out downstream revenue faster than any channel issue.

What you’ll hear

• How Cait defines a growth operating system across acquisition, nurture, and conversion
• Why early-stage teams need wide flexibility, while later-stage teams cap experimentation at ~10–20%
• A real example of reallocating spend that moved ROAS from 2:1 to 20:1—and why that was still not the end goal
• How broken trust (not missing features) kills retention, referrals, and revenue

Chapters

Timestamps from episode transcript

• 00:00 — Aspirational vs. functional promises and why trust breaks fast
• 01:14 — What a growth operating system actually is
• 02:50 — Compounding metrics, referrals, and overlooked revenue
• 04:16 — Early-stage vs. late-stage operating rhythm and spend mix
• 06:49 — $1M/month paid media example: foundation vs. experimentation
• 10:27 — Activation, funnels, and building demand before conversion
• 15:23 — Turning around a struggling ad program and rethinking ROAS
• 17:13 — North Star metrics, buyer intent, and what to track first

Links & resources

Guest
Cait Anderson — Chief Marketing Officer, Winston Francois
https://winstonfrancois.com

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Hank and Carly Schlissberg. Hank is the CEO of Evio Pharmacy Solutions, and Carly is a stay-at-home mom to their three daughters. Hank and Carly discuss their experiences as parents and entrepreneurs, sharing insights on managing time, setting priorities, and finding balance. They emphasize the importance of hiring exceptional people and prioritizing what truly makes a difference. Hank discusses how aligning incentives in the healthcare industry is key to growing and creating a sustainable, member-focused company. 

Follow ⁠Winston Francois⁠ https://winstonfrancois.com/ 

LinkedIn - https://www.linkedin.com/company/winstonfrancois/ 

X - https://twitter.com/WFdoesgrowth 

Instagram: - https://www.instagram.com/WFdoesgrowth 

TikTok- https://www.tiktok.com/@WFdoesgrowth 

Follow Jason Shafton: 

LinkedIn - https://www.linkedin.com/in/jasonshafton 

X - https://twitter.com/jasonshafton 

Instagram - https://www.instagram.com/jasonshafton/ 

TikTok - https://www.tiktok.com/@jshafton 

YouTube - www.youtube.com/@JasonShafton 

Follow Alyssa Fox:

Instagram: https://www.instagram.com/afox19/

Evio: 

https://www.evio.com/

X: https://x.com/EvioTeam

LinkedIn: https://www.linkedin.com/company/eviopharmacysolutions/

LinkedIn: https://www.linkedin.com/in/hank-schlissberg-17843/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Brian and Sam Rose, husband and wife duo and partners in Mvnifest, a single platform to manage your commerce operations, from concept to customer. Brian and Sam met in college and have been growing businesses and people together for nearly 20 years. They share their approach to parenting, business, and creating an environment of fun and generosity of spirit. They are no strangers to a late night and have created their own luck and success. Their mutual admiration, respect, and trust have fostered many successful businesses and three thriving kids.  

Follow ⁠Winston Francois⁠ https://winstonfrancois.com/ 

LinkedIn - https://www.linkedin.com/company/winstonfrancois/ 

X - https://twitter.com/WFdoesgrowth 

Instagram: - https://www.instagram.com/WFdoesgrowth 

TikTok- https://www.tiktok.com/@WFdoesgrowth 

Follow Jason Shafton: 

LinkedIn - https://www.linkedin.com/in/jasonshafton 

X - https://twitter.com/jasonshafton 

Instagram - https://www.instagram.com/jasonshafton/ 

TikTok - https://www.tiktok.com/@jshafton 

YouTube - https://www.youtube.com/@JasonShafton 

Follow Alyssa Fox:

Instagram: https://www.instagram.com/afox19/

Mvnifest: 

https://mvnifest.com/

Instagram: https://www.instagram.com/mvnifest/

X: https://x.com/sorryrobots

LinkedIn: https://www.linkedin.com/in/brian-rose-endless https://www.linkedin.com/in/samanthatrose/  https://www.linkedin.com/company/mvnifest/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Jessica and Marshall Morris, husband and wife duo and partners in HomeLife brands. They discuss the importance of relationships in business and parenting and the need to understand and support individuality. They also share their approach to parenting, which involves following their children's passions and providing guidance without stifling their creativity and independence. Jessica and Marshall Morris also share their resilience journey and how they have built businesses with impact that focus on saving animals and helping veterans. 

Follow ⁠Winston Francois⁠ https://winstonfrancois.com/ 

LinkedIn -https://www.linkedin.com/company/winstonfrancois/ 

X - https://twitter.com/WFdoesgrowth 

Instagram: - https://www.instagram.com/WFdoesgrowth 

TikTok- https://www.tiktok.com/@WFdoesgrowth 

Follow Jason Shafton: 

LinkedIn - https://www.linkedin.com/in/jasonshafton 

X - https://twitter.com/jasonshafton 

Instagram - https://www.instagram.com/jasonshafton/ 

TikTok - https://www.tiktok.com/@jshafton 

YouTube - www.youtube.com/@JasonShafton 

Follow Alyssa Fox:

Instagram: https://www.instagram.com/afox19/

HomeLife Brands: 

https://homelifemedia.com/

Instagram: @marshallsmorris @Jessicamariemorris

LinkedIn: https://www.linkedin.com/in/marshallsmorris/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this special Father’s Day episode, Jason flies solo and interviews Nick Aubin, the co-founder and CEO of Commons Clinic, about his experience as a dad and an entrepreneur. They discuss the challenges of balancing work and family life, the importance of being present and proactive as a parent, and the joy of watching their children grow and succeed. Nick shares his insights on the healthcare industry and the mission of Commons Clinic to provide accessible and affordable care. The conversation is filled with humor, honesty, and valuable advice for dads navigating the complexities of fatherhood and entrepreneurship.

Mentions and recommendations: 

Ikigai

Yoto

Tonies

Nanit

Follow Winston Francois: LinkedIn - https://www.linkedin.com/company/winstonfrancois/ Twitter/X - https://twitter.com/WFdoesgrowth Instagram: - https://www.instagram.com/WFdoesgrowth TikTok- https://www.tiktok.com/@WFdoesgrowth Follow Jason Shafton: LinkedIn - https://www.linkedin.com/in/jasonshafton X - https://twitter.com/jasonshafton Instagram - https://www.instagram.com/jasonshafton/ TikTok - https://www.tiktok.com/@jshafton YouTube - www.youtube.com/@JasonShafton Commons Clinic: https://commonsclinic.com/ LinkedIn: https://www.linkedin.com/in/nick-aubin-56883647/ LinkedIn: https://www.linkedin.com/company/commons-clinic/

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they engage in a fascinating conversation with Robbie and Emily Bent, the visionary co-founders of Othership. Othership is not just a platform, it's a transformative concept that combines a physical space and a mobile app. It's a solution to the pervasive issue of loneliness, offering a path to improved individual and collective health. Othership's unique approach fosters a sense of awe, belonging, and interconnectivity, enriching the human experience and leading to a more fulfilling life.

The conversation covers entrepreneurship, parenting, work-life balance, and personal growth. It delves into the challenges and rewards of building a business, the journey of becoming a parent, and the evolving definition of success.

Follow Winston Francois: LinkedIn - https://www.linkedin.com/company/winstonfrancois/ Twitter/X - https://twitter.com/WFdoesgrowth Instagram: - https://www.instagram.com/WFdoesgrowth TikTok- https://www.tiktok.com/@WFdoesgrowth Follow Jason Shafton: LinkedIn - https://www.linkedin.com/in/jasonshafton X - https://twitter.com/jasonshafton Instagram - https://www.instagram.com/jasonshafton/ TikTok - https://www.tiktok.com/@jshafton YouTube - www.youtube.com/@JasonShafton Follow Alyssa Fox: Instagram: https://www.instagram.com/afox19/ Follow Othership: Instagram: https://www.instagram.com/othership/ Instagram: https://www.instagram.com/othership.app/ TikTok: https://www.tiktok.com/@othership LinkedIn: Emily Bent - https://www.linkedin.com/in/emily-bent-2504082a/ LinkedIn: Robbie Bent - https://www.linkedin.com/in/robbiebent/ X - https://twitter.com/robbiebent1

Welcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox delve deep into the complexities of business and personal growth. In episode one, Jason and Alyssa open up about the intricacies of balancing work, life, and parenthood. They talk about some of the advice they have gotten that was “total bullshit,” and share the unique and creative way they decided to celebrate the birth of their second child. It may have involved a 20-person shoot, and burgers being thrown in people’s faces. Watch Motherhood is Hot! Youtube @WinstonFrancois.

How to build consumer app growth without defaulting to paid media.
For founders and operators scaling consumer subscription apps and looking for durable growth levers.

Dan Kessler joins Jason Shafton to break down how he thinks about consumer growth across partnerships, product loops, and app portfolio strategy. Drawing on work discussed from Headspace, Citizen, and The Mind Company’s apps Elevate, Balance, and Spark, he explains when partnerships actually create value, why early teams should not treat them as a silver bullet, and how Spark was designed around sharing instead of a hard paywall. The conversation gets specific on what makes a partnership useful, how “screenshotability” drives product-led growth, and why bundling multiple apps can create more value than forcing everything into one product.

• Dan’s framework for evaluating partnerships: audience access, brand equity, and speed
• Why Spark tracks screenshots and score sharing every day instead of relying on paid acquisition
• Why partnerships are hard to fund and measure for early-stage companies
• How to decide between one product, a portfolio of apps, and a bundle subscription

Timestamps from transcript.

• 00:00 — Why durable consumer growth starts with product loops
• 01:48 — Dan Kessler’s partnership framework: distribution, brand, and speed
• 07:24 — When partnerships belong in the growth playbook
• 11:09 — Screenshotability and how Citizen turned users into marketers
• 13:01 — How Spark used sharing and existing users to grow
• 17:47 — Why The Mind Company built a portfolio of apps

Guest
Dan Kessler — The Mind Company
LinkedIn

Mentioned
Elevate
Balance
Spark
Citizen

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

Episode #211: Elia Wallen — Building a $2B travel platform by serving SMBs

How a founder built a multi-billion dollar company in an overlooked market.
For operators deciding whether to chase hype markets or serve ignored customers.

Elia Wallen is the founder and CEO of Engine, a business travel platform that grew out of his earlier company Travelers Haven. What started as a corporate housing service expanded after customers repeatedly asked his team to book hotels for traveling workforces. Looking closer revealed a gap between consumer OTAs and enterprise travel management companies that left SMB travel largely unmanaged. In this episode, Elia explains how Engine built a $2B+ company by focusing on SMB customers, running high-touch outbound sales, and staying disciplined on capital while competitors raised and spent aggressively.

What you’ll hear

• Why SMB travel was a large but ignored market between OTAs and enterprise TMCs
• How Engine built growth through outbound “smile and dial” sales to smaller businesses
• What broke when Engine expanded from hotels into flights and cars
• Why Elia turned down additional capital and avoided hiring a traditional CMO

Chapters

• 00:00 — Finding an overlooked gap in business travel
• 02:30 — From Travelers Haven to Hotel Engine
• 03:41 — Why SMB travel stayed unmanaged
• 04:16 — Building an outbound sales motion for SMBs
• 06:25 — Expanding from hotels to flights and cars
• 08:18 — Why Engine took less capital than it was offered

Links & resources

Guest
Elia Wallen — Founder & CEO, Engine
Engine website

Mentioned
Engine new customer offer — $250 off when you mention “Frank Growth” to your account executive

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: Jason Shafton on LinkedIn

Product marketing only matters if it changes pipeline, adoption, or retention.
This episode is for founders, PMMs, and operators trying to make product marketing actually impact growth.

Seif Salama joins Jason Shafton to break down what product marketing really does when it works. Seif has led product marketing across companies like Google, Fanatics, Carta, and AngelList, operating at both massive scale and early-stage startup speed. The conversation focuses on the real job of product marketing: translating product truth into market truth and helping customers understand and decide—not just creating decks or launch messaging. Seif explains how positioning should be rooted in customer language, why most sales enablement content fails, and how product marketing should influence (but not own) pricing, packaging, and product decisions.

• Why great product marketing translates “product truth” into “market truth”
• How positioning fails when it isn’t rooted in real customer language
• Why one-pagers don’t close deals—and what sales teams actually need instead
• How to measure product marketing when attribution is messy

Timestamped chapters

• 00:00 — Why sales enablement one-pagers don’t close deals
• 01:50 — What product marketing actually does
• 03:15 — What separates revenue-driving PMM from slide factories
• 04:08 — How positioning works (and how to test if it’s differentiated)
• 06:42 — How great product launches are structured
• 11:35 — What sales enablement actually means in B2B
• 15:48 — Measuring product marketing impact
• 19:16 — What PMMs should do in their first 90 days

Guest
Seif Salama — Product Marketing Leader
LinkedIn

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

How to design data systems that actually drive business outcomes.
For operators building analytics, loyalty, or AI initiatives under real constraints.

Pat Ryan, with experience at Discover, Organizing for Action, and United Airlines, joins Jason to break down what “data systems designed for growth” actually means in practice. They discuss infrastructure decisions that last decades, why loyalty programs are fundamentally data engines, and how United leaned on its loyalty program during the pandemic when flying stalled. Pat explains the difference between rewards and true loyalty, why most AI initiatives fail the path-to-value test, and what his first 90 days look like inside a growth-stage company.

• Why every data investment needs a clear path to value
• How loyalty programs move customers up the value chain
• Where data systems break: infrastructure decisions that outlive you
• A practical 90-day plan: process first, then goals, then people, then strategy

Timestamps from transcript.

• 00:00 — Why data only matters if it drives value
• 02:13 — Designing systems for commercial outcomes
• 03:50 — Infrastructure risk and long-term tech decisions
• 05:52 — Loyalty vs. rewards: data vs. discounting
• 10:08 — Why data trust is cultural, not technical
• 14:22 — AI hype vs. real path to value

Guest
Pat Ryan — United Airlines
LinkedIn

Mentioned
Databricks

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

Outbound email is an impression now—not a response channel.
For seed to Series C revenue leaders building a real funnel and motion.

Lindsay Crittendon (CRO, Taylor Bird) breaks down how to build revenue strategy that persists—grounded in how customers actually use your product, not heroics. She explains why the first diagnostic is retention and product usage, why most “can’t close” problems are positioning problems, and how to define a real ICP that’s clear enough to make your CEO uncomfortable. You’ll also hear her decision rule for go-to-market motion (match price and buyer behavior), why founders own sales until $1–$2M in revenue, and how to design simple comp plans that don’t bankrupt you—starting with budgeting 20% for commissions.

• How to diagnose revenue: product usage/retention first, then positioning, then conversation quality
• How to define a real ICP (including a focused 500–600 company target list) and why focus beats “TAM”
• Why cold outbound email is mostly broken—and how to treat it as impressions instead of expecting replies
• How to pick PLG vs sales-led vs hybrid based on willingness to pay, and when to hire your first AE

Chapter topics (no timecodes).

• 00:00 — Why outbound is broken and email is just an impression
• 02:18 — Revenue strategy: persistent money over time (not heroics)
• 02:48 — What teams overlook: post-sale truth, customer usage, and what customers care about
• 04:16 — Diagnosing a revenue org: retention, positioning, and conversation quality
• 05:52 — ICP discipline: make it small, specific, and repeatable
• 07:11 — Choosing the right motion: match price and buyer behavior (PLG vs sales-led)
• 09:21 — Outbound today: stop expecting replies; use it for cheap impressions
• 10:25 — Minimum viable sales process: founder-led until ~$1–$2M
• 11:55 — Hiring and comp: budget 20% for commissions and keep plans simple
• 14:31 — Sales + marketing operating rhythm: partnership, respect, and shared accountability
• 16:23 — Speed round: product usage, discovery questions, stalled deals, and picking up the phone
• 17:15 — Building momentum: “what’s the first thing we can do together?” (mutual NDA example)
• 18:07 — Turnarounds: proving lost PMF with data, then fixing product and positioning
• 19:39 — Where to find Lindsay and what to reach out about

Guest
Lindsay Crittendon — CRO, Taylor Bird

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

How to design events where the right people actually meet and follow through.
For founders and operators building communities, networks, or community-led growth.

Kushagra Shrivastava is a builder and community investor behind Zoogler, a 40,000+ ex-Google alumni network. He explains how he defines “serendipity” as structured randomness within constraints, how he measures it through behavioral signals (like connection velocity), and what he considers non-negotiable when hosting events. We also cover why Zoogler outgrew a stack of tools like Google Sheets, Airtable, and Eventbrite-style platforms, what changed during the 2023 Google layoffs, and how his product Key uses intent to drive warm introductions for outcomes like hiring, fundraising, and business development.

• A practical definition of serendipity, “structured randomness within constraints,” plus how to measure it
• The 3 non-negotiables for events: pre-event intent collection, designed “collision moments,” and forced closure with a next step
• What breaks communities: optimizing for quantity (content and connections) instead of intent and outcomes
• A founder checklist for starting a community as an individual vs. as a brand and how to scale once you know what works

If transcript includes timestamps, use mm:ss or hh:mm:ss.

• 00:00 - Defining serendipity and how to measure it
• 06:20 - Zoogler overview: building a 40,000+ ex-Google network
• 07:18 - Minimum viable magic for events: intent, collisions, forced closure
• 09:32 - Key: turning intent into warm intros and outcomes
• 14:32 - Founder checklist: building community as a person vs. a brand
• 17:35 - Lightning close: the one takeaway

Guest
Kushagra Shrivastava - Builder and community investor (Zoogler; Key)

Frank Growth is a podcast about how companies actually grow, real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

Episode #206: Steve Dennis — How to Write Like a Human in the Age of AI

AI can generate endless copy. The new bar is making someone feel something.
This episode is for founders, marketers, and anyone who writes for a living and wants their work to connect.

Steve Dennis is a writer and ghostwriter who has shaped voices the world knows—including Andy Puddicombe at Headspace. Jason and Steve go back to the Headspace days, where Steve helped define the brand voice and coached writers (including Jason) on how to sound human on the page. In this conversation, they cover how to capture someone else's voice authentically, why vulnerability makes writing believable, and what AI still can't replicate.

What you'll hear

• Why your spoken word is where authenticity lives—stop "writing" and start speaking your story first
• The ghostwriter's test: can your closest friends read it and think it's your voice?
• What AI gets wrong: it engineers patterns, not meaning—it has no conscience, memory, or imagination
• The "remembering room" technique for evoking sensory detail and emotional truth

Chapters

• 00:00 — Cold open: Writing about mistakes is writing about being human
• 00:33 — Opening riff: Three traps of AI-era writing
• 02:33 — Steve's background and working with Andy Puddicombe
• 05:16 — How to disappear as a ghostwriter
• 07:27 — The biggest authenticity mistake: putting a dinner jacket on language
• 10:06 — The irreplaceable role of human writers
• 13:13 — Why AI can't access your memory bank
• 15:03 — Book recommendations: Stephen King and Robert McKee
• 17:38 — Where to find Steve and closing

Links & resources

GuestSteve Dennis — Writer
Twitter/X
InstagramAgency: Curtis Brown (London)

Mentioned
"On Writing" by Stephen King
"Story" by Robert McKee

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

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• Work with Winston Francois
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Episode #205: Jordan DiPietro — How to Turn an Audience Into a Community That Compounds Growth

Most companies stop at audience. This episode shows you how to build community that creates its own pipeline.
For founders and operators who want retention, not just reach.

Jordan DiPietro has built audience-to-community flywheels at The Motley Fool, The Hustle (inside HubSpot), and as CEO of Hampton. In this conversation, he breaks down the specific systems Hampton used to vet members—including raising the revenue threshold from $1M to $3M and personally reviewing every applicant video. He explains why trust compounds through radical transparency (like publishing every stock pick, good and bad, at Motley Fool) and how to pick a content medium you won't burn out on.

What you'll hear

• The difference between audience and community: if the party stops when you leave, you don't have a community
• How Hampton's vetting process filtered for members who give more than they take
• Why founder-as-creator is really about distribution, not personal branding
• The SVB crisis moment when Hampton's community self-organized faster than the company could respond

Chapters

• 00:00 — Cold open: Audience vs. community defined
• 00:27 — Introduction and Jordan's background
• 01:13 — The through-line: audience → trust → community
• 03:33 — Hampton's depth-over-breadth systems
• 05:15 — Founder's arbitrage: attention, trust, and taste
• 06:27 — SVB crisis: community self-organizing in real time
• 07:49 — Why founder as creator is no longer optional
• 09:32 — Minimum viable cadence for content creation
• 10:48 — Start with community from day one
• 11:55 — One operating principle for durable growth
• 13:11 — Where to find Jordan
• 13:52 — Closing takeaways

Links & resources

GuestJordan DiPietro — ex-CEO of Hampton, former leader at The Hustle (HubSpot) and The Motley Fool
Website / Newsletter (Signal Noise)

Mentioned

Hampton

The Hustle

The Motley Fool

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois
• Subscribe / Follow Jason