Bootstrapping to Billions
The podcast for owners who believe the goal of business is to stay in business — and still exit on your terms. Hosted by Chris Sacchinelli. Approaching 100,000 subscribers.
Ep 312 · How We Structured a Profit Exit Without Selling Five Exits of Ownership · LTEM | Marcus Vail |
Ep 309 · The Hidden Tax That Cost Me $2M at Close Five Hidden Taxes · Concentration Risk | Chris Sacchinelli |
Ep 305 · SAFERR vs. Convertible Note — Which Protects the Owner? Capital Structure · SAFERR | Sarah Kimura |
Ep 301 · Selling 30% and Staying in Control Partial Sale · Equity Management | David Okafor |
Ep 298 · What the QoE Auditor Is Actually Looking For Exit Readiness · QoE | Elena Marsh |
Ep 294 · Bootstrapping vs. VC — An Honest 10-Year Comparison Bootstrapping · Capital Strategy | Chris Sacchinelli |
Ep 290 · How AI Changed Our Transferability Score AI Readiness · Transferability | James Torrance |
Ep 285 · The Four Engines — Running All of Them at Once OWNABLE OS · Four Engines | Chris Sacchinelli |
Ep 278 · From $3M to $18M Without a Single Outside Dollar Bootstrapping · ProfitFlow | Priya Nair |
Ep 270 · Succession Is Not an Exit — Here's Why Succession · Family Business | Paul & Lin Hendricks |
- Long-Term Equity Management (LTEM)42 episodes — the discipline of managing ownership as a financial position.
- The OWNABLE OS38 episodes — the Four Engines and how to install them in a real business.
- Capital Strategy55 episodes — debt, SAFERR, partial sales, and when each one compounds vs. erodes equity.
- Exits & Succession61 episodes — the Five Exits of Ownership, sequencing, and how to exit on your terms.
- AI & Transferability18 episodes — how AI reshapes owner dependence, valuation, and exit readiness.
- Bootstrapping & Profit Design47 episodes — building capital-efficient businesses that compound without raising.
- Founder Conversations79 episodes — exited and nearly-exited founders on what the sale actually looked like.
- Five Hidden Taxes29 episodes — time cost, opportunity cost, concentration risk, illiquidity, bad capital.
- 2018Bootstrapping to Billions launchesFirst episode published. Format: solo breakdowns of ownership mechanics and LTEM principles.
- 2020Guest format introducedConversations with exited and nearly-exited founders added to the lineup. Audience doubles in 12 months.
- 2021Episode 100 milestone100th episode published — a retrospective on the most important lessons from 100 conversations.
- 2022YouTube launchFull video format added to the YouTube channel @bootstrappercap. Video grows faster than audio within 6 months.
- 2024100,000 subscribersApproaching 100K combined subscribers across YouTube, Apple Podcasts, and Spotify — without paid promotion.
- 2025300+ episodes in archiveSearchable back-catalog covering every major LTEM topic, capital structure, and exit type.
Frequently asked questions
Is the podcast free?+
Yes. The podcast is free on YouTube, Apple Podcasts, and Spotify. No paywall, no premium tier.
Who hosts the podcast?+
Chris Sacchinelli, founder of Bootstrapper Capital and Simple Holdings. He has spent more than a decade building, buying, and selling owner-led businesses.
Is the podcast connected to the OWNABLE OS?+
Yes. Episodes regularly reference the Four Engines, the Five Exits of Ownership, the Five Hidden Taxes, and the LTEM methodology. The podcast is the audio layer of the same discipline the OWNABLE OS delivers operationally.
Can I be a guest on the podcast?+
Guest episodes feature exited or nearly-exited founders with a real ownership story. Reach out to hello@bootstrappercapital.com with a brief summary of your business and exit situation.
Where can I find older episodes on a specific topic?+
The YouTube channel has full-text searchable titles and descriptions. Use the topic categories on this page as a starting point — or search the podcast archives on Apple Podcasts or Spotify.
- Guides →
Download the tools and templates that back up the podcast episodes.
- Books →
The written doctrine behind every episode — read the source text.
- Newsletter →
The reading version of the same methodology — one idea per week in writing.
- Long-Term Equity Management →
The discipline explained in full — complements every episode in the LTEM category.
Exit ready is capital ready.
The free OWNABLE Assessment takes about ten minutes and scores your Five Hidden Taxes in real dollars.