Playing the Long Game: A Masterclass in Building, Scaling, and Exiting w/ Bob Knorr of Timeless Tartans

Summary

Bob Knorr brings a rare blend of corporate insight, entrepreneurial experience, and mentorship wisdom to the show. In this conversation, he traces his journey from being an intrapreneur within a Fortune 50 company to founding multiple startups—bootstrapping, scaling, and even exiting with strategic precision. Bob’s deep commitment to mission, fairness, and listening to customer needs resonates throughout his storytelling. He also opens up about the intricacies of raising—or not raising—capital, navigating co-founder dynamics, and building enduring company culture.

He shares candid moments, such as turning down millions in VC funding to preserve ownership, creatively using credit cards and SBA loans to finance his business, and personally driving through remote Minnesota to train customers himself. Bob exemplifies the thoughtful, measured type of founder whose decisions aren’t just about economics but also values. His principles-driven approach, whether hiring employees or choosing strategic partners, brings clarity to the entrepreneurial chaos.

We close with reflections on the timeless lessons he draws from scripture—especially the book of Proverbs—and why his definition of success hinges more on service, wisdom, and impact than valuation. Whether you’re a first-time founder or a seasoned operator, this is a masterclass in grounded entrepreneurship.

Takeaways

1. Start with introspection – Before building a team, Bob urges founders to identify their own weaknesses so they can complement, not duplicate, themselves.
2. Not all funding is worth taking – He turned down $15M in VC to retain control, proving that smart capital timing is everything.
3. Find your first 50 customers – Don’t chase market size. Know exactly who will buy from you—and why—at launch.
4. Build relationships over pitches – Many early wins, like partnering with Mayo Clinic, came from relationship-first thinking, not aggressive sales.
5. Use capital creatively – From Costco credit card rewards to SBA loans, resourcefulness was a recurring theme in Bob’s journey.
6. Culture is built through clarity and repetition – Founders must constantly reinforce vision, while remaining flexible to market shifts.
7. Emotional compensation matters – Help employees connect their daily work to meaningful outcomes, especially in mission-driven fields like health.
8. Strategic exits come from leverage – His exit from Tapestry Medical was driven by regulatory influence and a valuable training network competitors needed.
9. Avoid early dilution – Bob recommends delaying or minimizing outside funding to retain equity and build on better terms later.
10. Proverbs as business guidance – He reads a chapter daily and credits biblical wisdom as the foundation of his personal and professional decisions.

Chapters

• [00:00] Early corporate experiences and entrepreneurial itch
  • Bob reflects on his first career chapter, building internal startups within a large corporation and how it prepared him for future ventures.
• [03:36] Taking the leap into entrepreneurship
  • A corporate defunding moment forces a fork in the road—Bob chooses to step out and found his own company.
• [06:35] Co-founders and complementary skillsets
  • He explains how identifying personal weaknesses led to finding the right technical co-founder with deep domain expertise.
• [09:55] Where to find the right co-founders
  • Bob shares practical advice on sourcing trustworthy partners and how shared vision and trust matter more than resumes.
• [11:44] Bootstrapping and early operations
  • He outlines how early funding came from personal resources and creative business model pivots instead of VC dollars.
• [14:53] Go-to-market strategy and customer validation
  • The critical importance of knowing exactly who your customers are, having spoken to them, and ensuring they’re ready to buy.
• [18:45] Competing in medtech against giants
  • Bob used insider knowledge and speed to outmaneuver entrenched competitors in a new healthcare segment.
• [22:01] Taking early high-stakes risks
  • He recounts personally flying out to train patients, losing money per session, just to earn credibility with Mayo Clinic.
• [26:53] Funding through credit cards and SBA loans
  • How Costco credit card cashback funded growth, and the shock of losing that line overnight in 2008.
• [33:02] Vision-setting and culture building
  • Bob dives into how vision must be firm yet flexible, and how emotional buy-in helps foster team alignment.
• [37:15] Hiring strategies and team scaling
  • The challenge of transitioning from generalists to specialists and maintaining connection as headcount grows.
• [41:05] Emotional compensation and mission alignment
  • Tapping into deeper motivation by showing employees how their work improves lives.
• [42:02] The principle of fairness in negotiations
  • His “you cut, I choose” philosophy applies to all business dealings—everyone should leave the table feeling respected.
• [44:51] Navigating exits with leverage
  • By owning critical infrastructure competitors needed, Bob sparked an acquisition bidding war.
• [49:21] Questions founders should be asking
  • Instead of obsessing over how to get funding, ask how to delay, minimize, or even avoid it.
• [51:31] What to do if starting from scratch
  • Bob says he’d spend all his time talking to potential customers—no product building until true needs are deeply understood.
• [52:26] A timeless tool: the Book of Proverbs
  • Daily wisdom from scripture continues to guide Bob’s business decisions, especially Proverbs 15:22.