All Episodes

Brock Blake: Lendio CEO, Small Business Funding, SBA Loans, Bootstrapping vs Debt vs VC

Brian Murphy: Fundraising $25B Across 44 Funds, $73B Merger, Private Equity, Secondaries, Buffett

Joseph Woodbury: The Airbnb of Storage, marketplaces, moats, raising $75M from a16z

Morgan Lynch: Pioneering the Gig Economy, LogoWorks, HP Exit, Needle, Build Angel, Startups

Cahlan & Colt: 10-Year DevMountain Reunion, Bootstrapping, Bootcamps, Acquisitions

Carine Clark: 4x CEO, First Colony Mortgage, Resilience, Beating Ovarian Cancer, Introvert, Leader

Matty Gay: Building Primo Golf, Signing Phil Mickelson, Grant Horvat & Ecommerce Apparel

Blake Modersitzki: Pelion VC, Venture Returns, AI, War Stories, Top Deals & Scale

Cap Table Red Flags: AI Rewriting Startup Investing, SaaS, Solopreneurs, Founder Splits & Vesting

Matt Holman: E-commerce Subscription Playbook, CPG, From Prison to Profit

Jon Richards: Nomatic, E-Commerce, Margins, CPG, Crowdfunding, Retail, Sourcing

Jeremy Andrus: Traeger Grills, Brand Moats, Company Culture, Scaling, Going Public

The Truth About Product Market Fit, PMF, Customer Interviews, Lean Startup

Dan Caffee: Sold Teem to WeWork for $100M, Startup Mistakes, Personal Family Tragedy

Sam Stoddard: TurboTax for Immigration, YC, VC, Exits

Matt Stapleton: Turning Excel Sheets into $480M, SaaS Ideas, Strategy, Startups

Dave Bateman: How he kept 60% of a Unicorn, Entrata, Bootstrapping, Magic Mushrooms, Silver, Scaling

Cydni Tetro: Disney R&D, Innovation, 3D Printing, Brandless, Startups, Coke, Tenacity, Women in Tech

John & Tyler go over the Carta Q3 Pre-Seed Analysis, Early Stage Trends, VC, SaaS

Ryan Westwood: Slow Down to Speed Up, His $250M Exit to Infosys, Buying 7 Competitors, Scaling

Paul Ahlstrom: The Origins of Nail It Then Scale It, Market Timing, Utah VC, AI

Johnny Hanna: Entrata’s $4B Journey, Homie’s Disruption, and Entrepreneurs Mental Health

Adam Weber: Sold Service Business to Build a SaaS Startup, Fundraising, Pest, Finding Confidence

Jeff Kearl: The Playbook for Iconic Brands, Stance, Skullcandy, Entrepreneurship

David Bradford: The Master Connector, Wozniak, Jobs, Gates, Eric Schmidt, Sergey, Novell, Microsoft

Jeron Paul: From Spreadsheet Idea to $419M Exit, SaaS, Salesforce Acquisition, Founder Journey

Startup War Stories That Will Save Your Company | Equity Splits, Bad Investors, Hiring

Ben Knell: Building a $100M+ Sales Engine, Family & Leadership, FBI, Pest Control, Business

Jeff Burningham: From Real Estate Tycoon to VC, Startups, Becoming Wise in the Age of AI

Case Lawrence: From Elon's Lawyer to Trampoline King, Sky Zone, Startup, Founder Story

Kurt Workman: Owlet Baby Sock’s $100 Million Journey | Startup, SPAC, FDA, Turn Around

Don't Make These Mistakes: Founder Regrets, PMF, Fundraising, QSBS, Hiring

Dustin Robins: Following Lean Startup all the way to $30M, Don’t Skip Steps, Scalability

Startup Elephants vs Unicorns: Why We Invest in Elephants, Valuations, VC, Fundraising, Strategy

Garrett Gee: The Secret $54M Snapchat Sale, Bucket List Family, Shark Tank, Raising VC

Adam Edmunds: $4B Entrata CEO on Podium's Growth, Allegiance Sale to MaritzCX, SaaS & GTM Metrics

Phil Kirkeiner: $150k to $7M with an Offshore Sales Team | Startup Scaling, SaaS, Remote Teams, CEO

Scott Johnson: Bootstrapping to a $1.5B Adobe Acquisition, Workfront, Motivosity, Product-Market Fit

Andrew Smith: From Tech to Restaurants, Problem Hunter Building a Food Empire, Scaling & Investing

"This Is a DEAL KILLER": VC's Pre-Seed Due Diligence Checklist, Cap Table, Rule 83B, Founder Equity

Travis Cook: The AI Software Revolution, Building a Top Dev Shop, Blockchain, Startup Investing

Craig Earnshaw: Destructive Founder Splits & Pitching Investors Confidently, Angel Investing, Exits

Brian Beutler: Pitching Genius Raises $100M at Alianza, VOIP-2-Cloud Pivot, CEO of the Year Insights

Evan Teshima: Bootstrapping ForeUP to a Massive SaaS Exit and the $400k Chess Game

Eric Smith: Smart Home Legend, Hotel Internet Inventor, Control4 IPO, & Founder Lessons That Matter

Startup Validation Roadmap, Founder Mistakes, SI's Bootcamp Frameworks, Real-World Pivot Stories

Bryan Christiansen: Bootstrapping to Millions in ARR, Landing Goldman Sachs, & Customer Obsession

Jared Ward & Brendon Beebe: Coding with AI, Overcoming Scaling Challenges, Founding Team Dynamics

AI Investments, Founding Teams, VC Market Trends, Startup Strategies

Jason Peterson: Selling Before Building, SaaS Success, Validation, Lessons Learned

Devin Shurtleff: Overcoming Challenges, Strategic Shifts, and Lessons from a CEO’s Leadership Legacy

Silicon Slopes Legend John Pestana on Omniture’s $1.8B Adobe Exit, Enterprise Sales, & VC Tradeoffs

The $22M Bet on SMS Marketing: Shane Murphy’s Startup Playbook

Avoiding Capital Pitfalls: Sustainable Growth and Effective Networking Strategies

AI Gold Rush, Startup Cycles, and the Art of Bootstrapping: What Every Founder Needs to Know

Our Journeys, Lean Startup Insights, Economic Cycles, and AI's Role in Modern Entrepreneurship