Back

Explore every episode of the podcast The Startup Different Podcast

Dive into the complete episode list for The Startup Different Podcast. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.

Rows per page:

1–50 of 103

TitlePub. DateDuration
Should We Kill Canada Post?14 Oct 202500:26:58

Canada Post is hemorrhaging money—over $5 billion in losses since 2018, with no end in sight. As postal workers walk off the job for the second time in a year, the Crown corporation is effectively insolvent, surviving only on a $1 billion government bailout.

But this isn't just a story about a strike. It's about an institution designed for 5.5 billion letters per year now delivering less than half that, while still maintaining the same infrastructure, the same costs, and the same workforce.

The world has changed. Canada Post hasn't. Can it be fixed, or is it time to let it go?

Key Takeaways:

The brutal math: Canada Post has lost over $5 billion since 2018 and is currently losing $10 million every single day, with labour costs of $50-60/hour compared to private competitors at $20-50/hour

Digital extinction: Letter mail has dropped from 5.5 billion pieces annually to just 2 billion, even as the number of Canadian households has grown—a trend that's irreversible and accelerating

The rural dilemma: Three-quarters of Canadians already use community mailboxes, but eliminating door-to-door delivery or privatizing threatens to leave remote communities without affordable service

In this episode, David and Chris cut through the rhetoric from all sides—union demands, government talking points, and business frustrations—to explore what it would actually take to save Canada Post, whether Canadians still need universal postal service in 2025, and what happens to workers and communities if we get this wrong.

Whether you're a small business owner tired of unreliable delivery, a postal worker fighting for your livelihood, or simply someone wondering why your mail keeps getting more expensive and less reliable, this conversation will challenge your assumptions about what Canada Post should be—and whether it has a future at all.

AI Workslop Is Killing Your Startup07 Oct 202500:27:38

AI was supposed to make us more productive, but something's gone terribly wrong. While AI usage at work has doubled since 2023, a stunning 95% of organizations see zero measurable return on their investment. The culprit? "Workslop" - polished-looking AI-generated content that lacks real substance and creates more work for everyone downstream. Workers are spending nearly two hours dealing with each workslop incident they receive, costing companies millions in lost productivity and something even more valuable: team trust.


In this episode, we break down the workslop phenomenon and why it's particularly dangerous for startups. We explore how AI has turbocharged an old problem (bad PowerPoints and rambling emails have always existed), examine real examples of workslop in the wild, and discuss why recipients view workslop senders as less creative, capable, and trustworthy. More importantly, we give entrepreneurs practical strategies to prevent their teams from falling into the workslop trap - because the difference between AI that augments your team and AI that destroys it comes down to how you implement it.


Whether you're considering AI tools for your startup or already knee-deep in implementation, this episode will help you avoid the $9 million mistake that's tearing teams apart. We'll show you how to spot workslop, build team commitments around quality over speed, and create a culture where AI enhances human judgment rather than replacing it with hollow busywork.

Do Founders Need To Be Famous?30 Sep 202500:26:51

In the age of social media CEOs and viral entrepreneurs, is personal fame the secret sauce to startup success?

This episode dives deep into one of today's most pressing questions for founders: whether building a personal brand is essential or just another distraction from building great products. We explore the fine line between authentic leadership and performative fame-seeking that's reshaping how we think about entrepreneurship.

What You'll Discover:

The Fame Factor - Why 93% of consumers now judge companies based on their CEO's social media presence, and what this means for your startup's credibility and funding prospects.

The Authenticity Paradox - How brand loyalty has fundamentally shifted from products to founders' personal stories, and why investors are increasingly betting on the person behind the pitch.

Smart Brand Building - Practical strategies for reducing advertising costs through strategic personal branding, leveraging user-generated content, and navigating the evolving influencer landscape—from mega-celebrities to nano-influencers.

The Long Game - Why building a meaningful personal brand requires consistent effort over time, and how to balance visibility with substance in your entrepreneurial journey.

Whether you're a first-time founder wondering if you need to become the next Elon Musk, or an established entrepreneur questioning your marketing strategy, this conversation challenges conventional wisdom about what it really takes to build consumer trust and drive business success in today's attention economy.

Perfect for: Founders, aspiring entrepreneurs, marketing professionals, and anyone curious about the intersection of personal branding and business success.

Are IPOs Dead?23 Sep 202500:22:22

The IPO market has hit a wall – but is this the end of the road or just a detour? In this eye-opening episode of Startup Different, we dive deep into the dramatic shift reshaping how entrepreneurs think about exits, growth, and building lasting value.

With IPO volumes plummeting and regulatory hurdles mounting, a new generation of entrepreneurs is writing a different playbook. Private equity isn't just for Wall Street anymore – it's becoming the exit strategy of choice for founders who want to maintain control while still cashing out. Meanwhile, search funds are quietly revolutionizing business acquisition, turning everyday entrepreneurs into industry consolidators.

But here's where it gets interesting: while traditional exit routes are evolving, AI is simultaneously opening unprecedented opportunities to disrupt established industries. We explore the emergence of "search and destroy" funds – a bold new approach where entrepreneurs systematically target and transform entire market segments using technology.

What You'll Discover:

  • Why the flood of private capital is making IPOs less attractive (and what this means for your startup)
  • How search funds are democratizing business acquisition for entrepreneurs without massive war chests
  • The hidden costs and long-term implications of going public that every founder should understand
  • Real strategies for using AI to identify and exploit inefficiencies in traditional industries
  • Why understanding true business value – not just growth metrics – is more crucial than ever

Whether you're a founder planning your exit strategy or an entrepreneur looking for your next opportunity, this episode reveals the new rules of the game in a post-IPO world.

Did They Finally Confront Elon?16 Sep 202500:26:08

What happens when the world's most ambitious entrepreneur sets his sights on a trillion-dollar payday? In this eye-opening episode of Startup Different, we dive deep into Elon Musk's unprecedented compensation proposal and unpack what it reveals about Tesla's astronomical ambitions.

We explore the staggering implications of Tesla's valuation targets and examine whether this bold vision represents the future of corporate compensation or a dangerous precedent. As Tesla pivots toward becoming an AI and robotics powerhouse, we analyze how this transformation could reshape entire industries—and what it means for aspiring entrepreneurs looking to carve out their own piece of the robotics revolution.

From navigating political headwinds to capitalizing on emerging opportunities in automation, this episode reveals the strategic thinking behind one of business history's most audacious bets.

Whether you're fascinated by Musk's unconventional approach or questioning the sustainability of such massive wealth concentration, this conversation will challenge your assumptions about leadership, innovation, and the price of transformational change.

Key Topics:

  • The mechanics and implications of Musk's trillion-dollar compensation structure
  • Tesla's evolution from car company to AI/robotics giant
  • Political challenges and opportunities in the current landscape
  • Untapped opportunities for entrepreneurs in the robotics space
  • The future of executive compensation and corporate governance


Tune in for a thought-provoking discussion that goes beyond the headlines to explore what this moment tells us about the intersection of ambition, technology, and capitalism in the 21st century.

8 Things Founders NEED to Know About AGI and the Singularity09 Sep 202500:29:17

Ready or not, AGI is coming - and it could reshape everything we know about business, work, and life itself.

In this eye-opening episode of Startup Different, hosts dive deep into the most consequential technology shift of our lifetime: Artificial General Intelligence. With predictions pointing to AGI's arrival as early as 2028, founders can't afford to ignore what's coming next.

Drawing insights from the AI2027 project and cutting-edge research, this episode unpacks eight critical things every entrepreneur needs to understand about our rapidly approaching AGI future. From the potential displacement of 40-60% of white-collar jobs to revolutionary breakthroughs in healthcare, the hosts explore both the unprecedented opportunities and existential challenges that AGI will bring.

But this isn't just about the technology — it's about the human side of the equation. What happens when machines surpass human intelligence? How do we navigate the emotional and psychological impacts? And what does it mean for the future of entrepreneurship when the rules of the game are about to be completely rewritten?

Whether you're feeling optimistic about an age of abundance or concerned about potential dystopian outcomes, this conversation will challenge your assumptions and help you think strategically about positioning your business—and yourself—for the AGI revolution.

The singularity isn't science fiction anymore. It's a business reality that's closer than you think.

7 Ways to Replace Your Co-Founder with AI02 Sep 202500:27:10

Before you panic—we're not suggesting you fire your business partner!

But what if AI could handle many of the roles you've been desperately trying to fill with that elusive "perfect co-founder"?

In this provocative episode of Startup Different, hosts Dave and Chris tackle one of the most controversial questions in modern entrepreneurship: Can artificial intelligence actually replace key founding team members? The answer might surprise you.

We break down exactly how solo entrepreneurs are using AI to fill critical gaps traditionally handled by co-founders—from technical development to marketing strategy to financial planning. But we also dive into the nuanced reality of where human partnership still reigns supreme, especially in sales and customer relationships.

You'll discover:

  • The 7 specific ways AI can step into co-founder-level responsibilities
  • Why the traditional "hunt for a technical co-founder" might be outdated
  • How AI-first startups are competing with fully-staffed companies (and winning)
  • The surprising areas where human intuition and relationships still dominate
  • Real strategies for building transparency around AI usage that actually builds trust
  • Why business valuations are shifting for AI-powered ventures


Whether you're a solo founder struggling to find the right partner or part of a team wondering how AI fits into your strategy, this episode challenges conventional startup wisdom. The future isn't about replacing humans—it's about radically reimagining what founding teams can look like.

Warning: This episode might make you rethink everything you know about building a startup team.

Do People Think You're Dumb Because You Use AI?26 Aug 202500:23:48

A thought-provoking conversation about something every tech leader needs to hear: the hidden biases around AI adoption in coding.

We dove deep into some uncomfortable truths:

  • Why women and older engineers face unfair judgment when using AI tools
  • How fear of "looking incompetent" is holding back entire teams
  • The real impact on job security fears among developers
  • Why cultural resistance to AI is creating workplace inequities


The most striking insight? The same AI tool that makes one developer "efficient and forward-thinking" can make another seem "less capable" - and those perceptions often break down along predictable demographic lines.

If you're leading engineering teams or navigating AI adoption in your organization, this conversation will challenge how you think about competence, bias, and the future of development work.

Should Founders Go On Vacation?19 Aug 202500:28:30

Think successful founders never take vacations? Think again. We bust the myth that grinding 24/7 equals success and share why stepping away might be the smartest business move you'll make this year.

Startup Hiring: Rookies vs. Veterans12 Aug 202500:33:27

New grad or seasoned pro? Every startup faces this hiring choice. We break down when fresh talent beats experience, why culture trumps credentials, and how to build a team that won't jump ship in six months.

Is Remote Work Over?05 Aug 202500:32:48

Everyone's obsessing over getting people "back to the office" – but what if we're solving the wrong problem? While AI transforms entire industries, we're still debating desk locations. Dave and Chris unpack the real data on remote, hybrid, and office work, revealing surprising truths about productivity, collaboration, and what employees actually need to thrive.

AI Took Your Job - Now What?29 Jul 202500:26:09

AI is replacing entry-level jobs—and most grads are stuck in resume purgatory. In this episode, David and Chris break down why your early 20s are the best time to start a business, even if you have no money, no idea, and no experience. This isn’t a hype fest—it’s a practical playbook for launching fast, learning fast, and building something real.


PODCAST LINKS


Website:

https://www.startupdifferent.com


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Apple Podcasts:

https://podcasts.apple.com/us/podcast/the-startup-different-podcast/id1707691707


Amazon Music:

https://music.amazon.com/podcasts/8db9bd4d-b64a-42f6-a3b5-3ad8c8578e96/the-startup-different-podcast


Castbox:

https://castbox.fm/ch/5595828


iHeartRadio:

https://www.iheart.com/podcast/269-the-startup-different-podc-123590551/


Overcast:

https://overcast.fm/itunes1707691707


Pocket Casts:

https://pca.st/249a4hrn


SOCIAL


LinkedIn:

https://www.linkedin.com/company/startup-different


Instagram:

https://www.instagram.com/startupdifferent/


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Chapters


00:00 – Intro: Can Grads Even Get Hired?

03:10 – AI's Impact on Entry-Level Roles

06:25 – Why Early 20s Is the Best Time to Start

09:40 – Chris’s Post-Dot-Com Startup Story

12:20 – Step-by-Step: From Skills to First Customer

15:35 – Product or Service? Start With Services

18:50 – Validation, Revenue, and Profit Early

22:10 – Final Thoughts: Starting From Scratch


Forget Ads - Go Guerilla22 Jul 202500:25:54

When traditional ads failed, we went full guerrilla—and it actually worked. From postcards to giant fake checks, we share the scrappy, creative tactics that got real results (and laughs) for our startup. If you're tired of burning cash on paid ads, this episode might just change your marketing playbook.


PODCAST LINKS


Website:

https://www.startupdifferent.com


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Apple Podcasts:

https://podcasts.apple.com/us/podcast/the-startup-different-podcast/id1707691707


Amazon Music:

https://music.amazon.com/podcasts/8db9bd4d-b64a-42f6-a3b5-3ad8c8578e96/the-startup-different-podcast


Castbox:

https://castbox.fm/ch/5595828


iHeartRadio:

https://www.iheart.com/podcast/269-the-startup-different-podc-123590551/


Overcast:

https://overcast.fm/itunes1707691707


Pocket Casts:

https://pca.st/249a4hrn


SOCIAL


LinkedIn:

https://www.linkedin.com/company/startup-different


Instagram:

https://www.instagram.com/startupdifferent/


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Chapters


00:00 – Intro: The Problem With Paid Ads

03:00 – Our Weirdest Guerrilla Wins

06:15 – Why Postcards and Fake Checks Worked

09:30 – Guerrilla Campaigns That Flopped

12:20 – What Makes a Good Guerrilla Idea

15:10 – Guerrilla vs Paid: Which Gets More Leads?

18:00 – Budget, Creativity, and ROI Reality

21:15 – Should Founders Go Guerrilla in 2025?


Do Social Ads Even Work?15 Jul 202500:25:06

Do social ads even work—or are you just paying bots to click "like"? In this episode, we break down our own experience with YouTube and Facebook ads, what Prof G had to say about it, and why most founders might be wasting their money. If you're bootstrapping and debating digital ads, listen before you spend a dime.

PODCAST LINKS


Website:

https://www.startupdifferent.com


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Apple Podcasts:

https://podcasts.apple.com/us/podcast/the-startup-different-podcast/id1707691707


Amazon Music:

https://music.amazon.com/podcasts/8db9bd4d-b64a-42f6-a3b5-3ad8c8578e96/the-startup-different-podcast


Castbox:

https://castbox.fm/ch/5595828


iHeartRadio:

https://www.iheart.com/podcast/269-the-startup-different-podc-123590551/


Overcast:

https://overcast.fm/itunes1707691707


Pocket Casts:

https://pca.st/249a4hrn


SOCIAL


LinkedIn:

https://www.linkedin.com/company/startup-different


Instagram:

https://www.instagram.com/startupdifferent/


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Chapters


00:00 – Intro: Ads vs Organic

02:30 – What Happened With Our YouTube Ads

06:00 – Facebook Ads: Cost and Conversion

09:10 – Prof G's Take: Do Social Ads Work?

12:40 – How to Know If Ads Are Working

15:30 – The Role of Trolls and Bots

18:10 – Should Founders Use Paid Social Early?

21:00 – Final Verdict: What We Learned About Ads


Why 90% of Startups Should Avoid Resellers08 Jul 202500:27:52

Most founders dream of scaling fast, but resellers can quietly kill your margins, brand control, and growth velocity. In this episode, David and Chris break down real-world pitfalls from founders who handed off sales too early—and paid for it. If you're considering a reseller strategy to accelerate revenue, this is your warning shot (and what to do instead).


PODCAST LINKS


Website:

https://www.startupdifferent.com


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Apple Podcasts:

https://podcasts.apple.com/us/podcast/the-startup-different-podcast/id1707691707


Amazon Music:

https://music.amazon.com/podcasts/8db9bd4d-b64a-42f6-a3b5-3ad8c8578e96/the-startup-different-podcast


Castbox:

https://castbox.fm/ch/5595828


iHeartRadio:

https://www.iheart.com/podcast/269-the-startup-different-podc-123590551/


Overcast:

https://overcast.fm/itunes1707691707


Pocket Casts:

https://pca.st/249a4hrn


SOCIAL


LinkedIn:

https://www.linkedin.com/company/startup-different


Instagram:

https://www.instagram.com/startupdifferent/


YouTube Channel:

https://www.youtube.com/@StartupDifferent


Chapters


00:00 Introduction and Context of Reseller Partnerships

06:33 Challenges Faced with Reseller Partnerships

12:39 The Importance of Direct Customer Interaction

21:48 When Reseller Partnerships Can Work

26:37 Final Thoughts on Reseller Strategies


Push, Pivot, or Pull the Plug?01 Jul 202500:28:06

A founder rockets from plateau to $120M revenue and a $1.5B valuation—only to see a 50%+ revenue crash two years later. David and Chris break down the rollercoaster and the brutal decisions behind it. At the end of the day, when your startup stalls or surges how do you know whether to push, pivot, or pull the plug?

How Fear Fueled a $100B Brand24 Jun 202500:26:54

Most people run from failure—but what if it’s the very thing that drives you? In this episode, David and Chris unpack how fear fueled Howard Schultz’s relentless pitch for Starbucks, despite hearing "no" 217 times. Why do some founders push through while others freeze—and what’s really holding you back?


The Worst Trailer of All Time23 Jun 202500:01:32

Bros, Business, Banter. That's us.

It's the trailer for the Startup Different pod.

Is AI Ruining US? (And Maybe Your Kids?)17 Jun 202500:28:58

If every meaningful win in your startup came from struggle...what happens when AI takes that away? Chris hits the wall building with AI tools, David wonders if his kids will ever build resilience, and together they unpack whether AI is eroding the effort that makes real growth possible. This one's for the founders who've earned their scars—and wonder if the next gen ever will.


Will ChatGPT Crush Your AI Startup?10 Jun 202500:28:41

Think your AI startup is safe? Think again. In this episode, we unpack how foundational models like ChatGPT are steamrolling niche platforms by absorbing their features overnight—and what you can do to survive. From building unique integrations to niche-first moats, David and Chris share five hard-won lessons for AI founders trying to stay in the game before OpenAI levels the field.


The 5 lessons?

  1. Don't Compete on Core AI Capabilities
  2. Build Moats with Unique Integrations
  3. Focus on UX and Workflow, Not Accuracy
  4. Target a Niche and Go Deep
  5. Build to Exit, Not to Last Forever

Who Can CONFRONT Elon? 03 Jun 202500:29:03

We're trying a new format with the pod. Let us know what you think. Today it's "who can confront Elon"? In this unfiltered and wickedly funny episode, David and Chris explore how one man’s ego—Elon Musk—has torched Tesla’s brand, stock, and reputation, all while loyal fans quietly peel logos off their cars. From a 71% profit nosedive to Cybertruck chaos, it’s a masterclass in founder risk, brand backlash, and why empathy still matters. #ElonMusk #TeslaFail #StartupPodcast #Cybertruck #TeslaStock #BrandReputation #BootstrappedFounders #StartupDifferent


Is Ego Killing Your Startup?27 May 202500:32:12

What if your biggest growth block isn’t funding or strategy—but you? In this episode, we explore how ego quietly sabotages leadership and limits your team’s potential. Learn how emotional intelligence, real feedback, and a shift in mindset helped Carrie Fabris build a business helping execs lead better—without the burnout.


Skip the Payroll - Keep the Progress20 May 202500:31:19

What happens after you exit your startup and don't want a boss again? Taylor Crane shares how that moment led to a new way of working—and a new way of thinking about early hires. We dig into product lessons, co-founder dynamics, and what fractional roles look like behind the scenes. Plus, we cover when bringing on part-time leadership is actually smarter than hiring full-time.


Can You Grow Too Fast?13 May 202500:26:14

She quit her job, had no funding, and started fermenting cider in a garage with her husband. What could go wrong?! Hint: it's not what you think. Within a year, Alicia Hardman and her hubby were running a 10,000 sq. ft. winery with lines out the door—thanks in part to a viral swing table. But what happens when your startup grows faster than you can manage? Was all that growth a good thing?

Crisis Hit. $15M ARR Later, She Leveled Up05 May 202500:31:23

When COVID wiped out her luxury event business, Virginia Frischkorn didn’t just survive—she reinvented. By turning her workflows into software, she launched Partytrick, a SaaS company now on track for $15M ARR. What started in crisis became a better business than she ever imagined.


15 Jobs; 1 Multi-Million Exit29 Apr 202500:36:07

Before she turned 22, Jodie Cook had worked 15 different jobs — from mystery shopping to football stadiums. That wild ride set her up for a seven-figure exit, a global digital nomad life, and her latest venture, Coachvox. In this episode, Jodie shares how early hustle shaped her entrepreneurial mindset and why AI is the next frontier for scaling personal brands.


The Retail Investor Revolution22 Apr 202500:27:32

Retail investors represent 53% of the investing market. 🤯

In this episode, we break down our chat with Jane Crowell of Particle Capital and what founders get wrong about funding. We explore smarter paths to capital, the rise of retail investors, and why founder-led sales still matter. Plus, the mindset shift that separates resilient entrepreneurs from the rest.


Mo VCs, Mo Problems: Raising Without the Grind15 Apr 202500:30:49

Tired of chasing VCs and getting ghosted? Jane Crowell drops in to share how Particle is flipping startup funding on its head—connecting founders to capital without the pitch deck circus. If fundraising feels like a full-time job, this episode shows you how to skip the grind and get back to building.

A Boring Multi-Million Dollar Game 08 Apr 202500:32:36

Ever heard of someone getting robbed—only to land their dream job days later?

Melissa Cash’s journey from Disney to co-founding Pok Pok is full of wild turns, but her startup’s genius lies in something deceptively simple: it’s intentionally a bit boring. In this episode, we explore how quiet design, thoughtful screen time, and serendipitous moments led to a kids’ app that actually respects how kids play.


From $0 to $1.6B: The Story of a Telecom Unicorn01 Apr 202500:42:57

What does it take to build a billion-dollar company from scratch—in one of the toughest, most regulated industries in the world? Brice Scheschuk, co-founder of Wind Mobile, joins us to unpack the raw, real story behind a $1.6B exit that nearly didn’t happen. From regulatory wars to hiring 1,000 people in a single year, this is a gritty, no-BS blueprint for scaling a unicorn under fire.

Founder After Forty: How a Midlife Crisis Led to Midlife Mission25 Mar 202500:38:20

What if the second half of your life held more purpose than the first? Physician-turned-founder Brian Mahoney shares how a midlife pivot and a deep sense of mission led him to launch a startup transforming surgery recovery—before the surgery even starts.


Win at business AND get ripped18 Mar 202500:30:42

From selling bootleg software as a teenager to exiting a successful SaaS company, Anthony’s entrepreneurial journey is nothing short of fascinating. In this recap, we break down the hustle, the bold pivots, and the key lessons from his story—like why fearlessness in sales matters and how spotting the right opportunity can change everything. Plus, we debate whether entrepreneurs are truly 'born' or 'made.' Welcome to Startup Different!

Body & Business: How Anthony Ng Monica Built Two Successful Ventures from Scratch11 Mar 202500:34:50

Anthony shares his remarkable path from selling pirated software as a 12-year-old to building and exiting a 70-employee, bootstrapped e-commerce bundling platform. Now running Daily Body Coach, he explains how his entrepreneurial mindset helps executives maintain peak physical performance while managing demanding business lives. Welcome to Startup Different!

Playing the Startup Long Game WORKS04 Mar 202500:25:54

In this episode, we dive into the inspiring and unfiltered journey of Jess Chan, founder of Longplay. From navigating personal challenges to scaling an agency that champions retention marketing, Jess shares valuable insights, startup myths, and a jaw-dropping tale about an employee that sounds like it belongs in a crime-drama.

From Setbacks to Strengths: How Jess Chan Built Entrepreneurial Resilience For Longplay25 Feb 202500:32:22

On the show today, we’ve got Jess Chan, founder and CEO of Longplay. She’s an expert in retention marketing who’s built an eight-figure business, and she’s here to share some seriously useful lessons for entrepreneurs. Oh and she also tells us one of the wildest HR stories ever. It’s Startup Different.

Navigating Catastrophes and Capital18 Feb 202500:30:31

Last week we spoke to the fantastic Rob Levin, seasoned entrepreneur and investor. We deep dive on how he’s an accidental entrepreneur, how he asks for (and gets) money, and the age old debate of Toronto vs Des Moines. Welcome to Startup Different!

Scaling Smart: Rob Levin’s Guide to Business Growth, Funding, and Resilience11 Feb 202500:38:10

Robert Levin is a seasoned investor and operator with a robust background in strategy, growth and mergers and acquisitions. This week we talk to him about what it means to scale a startup worth tens of millions and how to manage the WFIO moments.


It's VC, funding, and pivots on Startup Different!


Building Beyond Unicorns and Redefining Startup Success04 Feb 202500:27:43

This week we go deep on our interview with Natalie Kaminski of JetRockets. We dig into the mighty middle, the Russian-Ukraine war, and taking all the work you can find. It’s Startup Different!

Empathy and Innovation: Natalie Kaminski’s Journey from Coder to CEO28 Jan 202500:35:37

Today, we’re chatting with Natalie Kaminski, the founder and CEO of JetRockets. She’s a tech entrepreneur with a knack for empathetic leadership and a powerful story about moving her entire company to align with her values.

Firefighters, Funding, and Pivots: Chris Memmott’s Path to Success21 Jan 202500:38:22

Today on Startup Different we talk to our old pal, Chris Memmott. He has over 15 years of sales and leadership experience within high-growth startups and has even had his own successful (albeit bumpy!) exit. We’ll cover his journey and what to watch out for when selling your business baby.


It’s acquisition time on Startup Different!

Were we Boss-Holes? The Secrets of Leadership Transformation14 Jan 202500:28:01

In this recap, we’re diving back into our chat with Catherine Bell, where she dropped some incredible gems about mixing purpose and profit as an entrepreneur. Whether it’s building a strong team culture or turning mistakes into growth moments, we’ve pulled together the best insights for you to level up your business game. Bonus: we also press Chris on his Boss-Hole past and is a hot dog a sandwich. It’s startup different!

Can You Balance Profit and Purpose? A Conversation with Catherine Bell (Season 6, Episode 1)07 Jan 202500:28:58

Can you balance profit and purpose?


Today’s guest is Catherine Bell, founder of The Awaken Company, and she’s all about transforming how we think about business. From building healthy cultures to leading with self-awareness, Catherine shows how your company can be a force for good while thriving along the way. Welcome to Season 6 of Startup Different.

Best Known Beats Best: Key Business Insights from Matt Watson’s $150M Exit (Season 5, Episode 13)31 Dec 202400:26:37

In this episode of Startup Different, we reflects on the journey of scaling businesses and the importance of exits, while debriefing our conversation with serial entrepreneur Matt Watson. The conversation delves into the significance of having a well-known product over just a good product, the necessity of execution, and the critical role of hiring the right talent at the right time. Additionally, the discussion touches on the interplay of luck and preparation in achieving business success, providing valuable lessons for entrepreneurs.

Scaling and Success: Matt Watson on Building and Exiting Multiple Startups (Season 5, Episode 12)24 Dec 202400:29:12

In this episode of Startup Different, Matt Watson, a serial tech entrepreneur, shares his journey of founding and exiting multiple startups, including a $150 million exit. He discusses the importance of execution, the challenges of scaling a business, and the role of timing and luck in achieving success. Matt emphasizes the need for product-market fit, the significance of key hires, and the complexities of offshoring development. He also addresses the impact of funding on scaling and shares insights on managing burnout as an entrepreneur. The conversation concludes with Matt's advice on being the best known in your field rather than the best at what you do.

Finding Goldminds: Key Lessons from Cynthia Arscott’s Mindfulness Startup (Season 5, Episode 11)17 Dec 202400:23:48

In this episode of Startup Different, we recap our interview with Cynthia Arscott, the founder of Goldminds, an app designed to help children sleep better. The conversation explores Cynthia's journey from tech to entrepreneurship, the challenges of transitioning from in-person to digital solutions during the pandemic, and the importance of working smarter rather than longer hours. We discuss the unique features of the Goldminds app, its market validation through a minimum viable product, and the significance of niche marketing in achieving business success. The episode concludes with insights on engaging with influencers and the promising future of Goldminds.

Get your Kids to Sleep: Cynthia Arscott’s Goldminds App for Children’s Wellbeing (Season 5, Episode 10)10 Dec 202400:29:27

In this episode of Startup Different, Dave and Chris interview Cynthia Arscott, the CEO and founder of GoldMinds, a mindfulness app for kids. Cynthia shares her personal journey from struggling with anxiety as a child to discovering the benefits of mindfulness and meditation. She discusses the evolution of her business from in-person mindfulness classes to a digital app, especially during the COVID-19 pandemic. The conversation highlights the importance of creating engaging content for children, targeting different age groups, and navigating competition in the app market. Cynthia emphasizes the significance of consistency over hard work in entrepreneurship and the importance of profitability.


Beyond Technical Skills: Key Communication Lessons from Expert Matt Reesor (Season 5, Episode 9)03 Dec 202400:31:40

Are entrepreneurs in Canada less motivated than their US counterparts? Last week, Matt Reesor gave us his take and identified how Canadian firms need to compete. Today, Chris and I dig deeper into the complexities of the Canada versus US competitive landscape. Welcome to Start Up Different.

The Power of Communication: Matt Reesor's Lessons for Startup Founders (Season 5, Episode 8)26 Nov 202400:33:24

This week we're talking about entrepreneurship, Canada, and politics. Our guest is the fantastic Matt Reesor. Matt's expertise lies in understanding how the dynamics of interpersonal communication contribute to the success of plans and ideas. He has trained thousands of MBA and Masters students at Queen's University Smith School of Business in Canada and Nagoya University of Commerce and Business in Japan. Through his company, Reemark Communications, Matt has partnered with leading organizations, to provide communications consulting and training services.


Startup Different, Engage.

Courageous Entrepreneurship - Lessons from Octavia Goredema (Season 5, Episode 7)19 Nov 202400:26:08

In this episode, we unpack our incredible conversation with Octavia Goredema, founder of Fire Memos. We explore themes of employee appreciation, the importance of stepping outside comfort zones, and the myths surrounding solo founders and technical co-founders. We also highlight the need for emotional support in entrepreneurship, the challenges of prioritization, and the innovative spirit of Fire Memos in celebrating achievements within organizations.

Breaking Barriers and Building Businesses: Octavia Goredema’s Startup Journey (Season 5, Episode 6)12 Nov 202400:35:06

Octavia Goredema is the CEO and founder of Fire Memos, a software company dedicated to igniting careers. The platform empowers employees to record and recognize their work accomplishments with AI powered career coaching.

She’s also an acclaimed career expert: she’s the author of "PREP, PUSH, PIVOT: Essential Career Strategies for Underrepresented Women", the host of the Audible Original series "How to Change Careers with Octavia Goredema", and has been featured on CNN, Harvard Business Review, and Fortune.

Today we’re seeing stars on Startup Different!

© My Podcast Data · Independent project · Data from Apple & Spotify