Bootstrapper Capital
Hosted by Bootstrapper Capital
A tactical podcast for founders on the mechanics of building, funding, and exiting a business with maximum ownership.
This is a case-study-style interview show that deconstructs the full lifecycle of a business, from inception to a liquidity event. Host Chris Sacchinelli interviews founders who have successfully sold their companies, focusing heavily on the financial and operational mechanics of the exit. Conversations dig into bootstrapping vs. venture capital, deal structures, earnouts, and the often-unspoken psychological challenges a founder faces post-acquisition.
“Unlike many business podcasts focused on growth hacks or inspirational stories, this show zeroes in on the financial, legal, and emotional realities of an exit. The recurring "Exited Series" provides a rare, candid look at the mechanics of deal structures, the complexities of earnouts, and the difficult realities of post-acquisition integration.”
Who hosts this show
Chris Sacchinelli hosts this deep-dive interview show focused on the practical details of building and exiting a business. A serial entrepreneur who has built and exited multiple businesses without venture capital, Sacchinelli now focuses on helping founders transition from operators into true owners. The podcast is an extension of his work at Bootstrapper Capital, a firm dedicated to "Long-Term Equity Management" for small and medium-sized businesses.
Credentials & credits
- Founder & CEO of Simple Holdings
- Founder of Bootstrapper.ai
- Author of "OWNABLE" and "Exit with Ownership"
- Host of the Bootstrapping to Billions podcast
- Founder of one of Connecticut's first AI accelerators with IBM
Other ventures
- Bootstrapper.ai (SMB platform)
- Simple Holdings (Holding company)
- Bootstrapper Media (Media company)
- Exited. (Media and community for exited founders)
- SMB Accelerator
What kind of podcast
- Country
- United States
- Region
- usa
When new episodes drop
- 01
- 02
- 03
- 04
- 05
- 06
Notable episodes
- 01Brandon Harris Built Digital Real Estate Into a $54M Media Exit
A detailed account of building a media company from valuable social media handles and the complex, often conflicting reality of a $54M exit with a multi-part earnout.
- 02Michael Kapps Epic Pivot w/ Vitalk into a Gympass (now Wellhub) Exit
Chronicles a six-year journey of pivoting from an SMS health app to a corporate mental health platform, culminating in an acquisition by a major wellness company.
- 03How to Monetize Media Sponsorships, Retention, Thumbnails, and Growth
A tactical breakdown with former Playmaker CGO Devon Harris on the specific analytics and strategies used to monetize original content on platforms like Snapchat.
What you'll be asked on this show
The format is a one-on-one interview, with host Chris Sacchinelli methodically guiding guests through their company's history. He consistently aims to extract "live learn lessons" by asking specific, chronological questions about funding, team building, monetization, and the exit itself. The tone is analytical and professional, akin to a live business school case study.
Questions Bootstrapper Capital keeps coming back to
- “How did you get started with the business?”
- “Take us through the revenue streams within the business.”
- “What did the team look like?”
- “Was this bootstrapped or did you bring on capital?”
- “What would you have done better, faster, or sooner?”
- “What was the 'live learn' experience in terms of friends and family?”
- “How did the exit come about?”
- “What was it like getting life-changing money and losing this thing you built?”
Signature segments
- · Exited Series
- · Live Learn Lessons
- · Bootstrapping to Billions
- · Trust the process, commit to the journey.
Topics covered repeatedly
Who gets booked here
The show primarily books founders who have successfully exited their bootstrapped or venture-backed companies. Guests typically come from the tech, media, and finance sectors and are willing to share candid, detailed accounts of their acquisition process and its aftermath.
- Michael Kappson Bootstrapping to Billions E47: Michael Kapps Epic Pivot w/ Vitalk into a Gympass (now Wellhub) Exit
- Devon Harrison Bootstrapping to Billions E46: How to Monetize Media Sponsorships, Retention, Thumbnails, and Growth
- Brandon Harrison Bootstrapping to Billions E45: Brandon Harris Built Digital Real Estate Into a $54M Media Exit
- Michael J. Frankon Bootstrapping to Billions E44: Behind The Wall Street Exit. How Market Makers Really Make Money.
- Alex Shartsison Bootstrapping to Billions E43: Alex Shartsis Built a $10M Startup. Then Venture Math Almost Broke It
- Nellie Akalpon Bootstrapping to Billions E42: Nellie Akalp Turned $100 Into a 17 Year Bootstrapped Empire Post Exit
Where to find this show
Audience & reach
The podcast attracts B2B sponsors whose services are directly relevant to business owners, such as LLC formation (Tailor Brands), all-in-one business software (Odoo), and SEO/marketing tools (Ahrefs). Sponsorships are read by the host during the episodes.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
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People also ask
- What is the host's real name?
- The host is Chris Sacchinelli, a serial entrepreneur and founder of Bootstrapper Capital.
- Is the Bootstrapping to Billions podcast still active?
- Yes, the podcast releases new episodes on a weekly basis.
- What is the format of the show?
- It is a long-form interview podcast where host Chris Sacchinelli speaks with founders and operators about building and exiting their businesses.
- Who are the typical guests on the show?
- The show features founders who have exited their companies, along with operators and experts in fields like media, finance, and technology.
- Where can I listen to the podcast?
- The podcast is available as video on the Bootstrapper Capital YouTube channel and on audio platforms like YouTube Music.
- How can I be a guest on the podcast?
- The official podcast website has a "Be a Guest" link for inquiries.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
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