Issue #348: A Year In Review

A foundational year for ownership

Author

Bootstrapper Capital
December 27, 2025

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We actively invest in B2B service and SaaS businesses who prioritize building a long-term sustainable business.

Welcome back fellow investopreneurs!

❝

Before we close the year, I want to thank you for being a meaningful part of this journey.

Knowing that you’re reading this matters. It’s why we invested in 2025 as a foundational year.

A year spent proving that long-term equity for bootstrapped owners can be measured, built, tracked, and financed ... not just talked about.

Here’s a quick look back ... and thank you for the support throughout this journey!

- The Bootstrapper Team.

2025 by the numbers

  • Nearly $100M of Equity Under Management (EUM) built and tracked on Bootstrapper.ai

  • $12.9M+ of net new equity created for owners on platform in under 6 months of tracked data

  • Dozens of capital partners added to our private capital marketplace as we rolled out OWNABLE Certification as a new standard for durable, transferable businesses

  • Over a dozen businesses listed to exit with ownership, representing $15M+ in potentially life-changing transactions

  • 3 major platform launches

    • 2/4/25 ... our first launch (honestly, soul-crushing)

    • 5/25/25 ... traction and proof of a working model

    • 10/4/25 ... steady-state equity building as we began defining a new category

  • My book, Exit With Ownership published 7/7/25 ... 3,000+ copies sold

  • Bootstrapping to Billions podcast launched 7/29/25

    • 21 episodes

    • 500,000+ total views

    • 37,000+ subscribers

    • 20,000+ hours watched

  • Launch of the Bootstrapper Index, laying the groundwork for the largest database of bootstrapped companies, and adding to our war chest of free resources we want to provide to owners in our ecosystem

  • Our first-ever Bootstrapper LIVE! events, with plans to double down in FY26

  • A growing network of certified OWNABLE bookkeeping and ProfitFlow partners, plus the launch of our media partner program

  • 68 newsletters sent, 2.5M emails delivered, reaching 53,758 unique readers

  • An incredible 4,166 SMBs engaged with us this year!

Not bad for a year we’d describe as... foundational.

Over the course of this year, a pattern became impossible to ignore.

The owners who get the most value from Bootstrapper are not:

  • early-stage founders chasing product-market fit

  • hobby businesses

  • people looking for quick wins, hacks, or motivation

They are owners who already have something real.

Our ideal clients are:

  • Profitable SMB owners

  • Typically $1M–$20M in revenue

  • Often founder-led service, software, or durable niche businesses

  • Carrying most of the risk personally

  • And quietly wondering if the business they built actually works for them

They don’t want hype.
They don’t want growth at all costs.
They don’t want to sell tomorrow ... but they do want the option.

They want:

  • More profit without more chaos

  • Less personal risk

  • Clean financials

  • Transferable operations

  • Access to good capital, not desperate capital

  • And the confidence that if they ever exit ... it will be on their terms

That’s who we’re building for.

Which brings us to where we’re going.

Next year is not about experimenting.
It’s about execution.

In 2026, Bootstrapper becomes a firm singularly focused on one outcome:

Helping owners build assets.

That means:

  • Doubling down on equity-first operating discipline

  • Expanding OWNABLE Certification as a market signal

  • Growing our capital marketplace for owners who earn the right to capital

  • Scaling platform-driven service delivery through certified partners

  • And continuing to build the data layer that makes ownership measurable

No noise.
No pivots.
No chasing trends.

Just methodical, long-term equity building.

So here’s the clear call-out as we head into the new year:

If you own a profitable business
If you want to reduce risk without losing control
If you care more about owning well than exiting fast
And if you want to build something that pays you now and later

You’re in the right place.

And if you’re not there yet ... we’ll keep publishing, teaching, and building the tools to help you get there.

Thank you for being part of this foundation year.

The real work starts now.

See you in the new year,
Chris

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