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In Feb 2020, a venture capital (VC)-backed legal marketplace called UpCounsel announced it was shutting down after burning through $26 million in investor capital. Its development team had been acqui-hired. The company had no staff, no funding, and no runway. It was dead.

One week later, Enduring Ventures bought the shuttering company and got to work.

They transformed UpCounsel from a marketplace into a Software as a Service (SaaS) platform charging lawyers $15,000–$30,000 per year. Within 15 months, the business was generating $3-4 million in annual recurring revenue (ARR). It then raised $3.9 million through crowdfunding.

That deal tells you everything about Enduring Ventures: entrepreneurs who see value where others see wreckage, move fast, restructure aggressively, and hold forever. It was one of the models that showed me the Baby Berkshire playbook wasn't just theoretical… Someone was actually doing it.

Enduring Ventures was founded in December 2019 by Xavier Helgesen and Sieva Kozinsky – two serial entrepreneurs who had spent years on both sides of the venture capital table and decided they wanted no part of it anymore.

Xavier had built Better World Books into a multi-million dollar e-commerce business before co-founding Zola Electric, the leading solar company in Africa – 1 million users, $155 million raised, backed by Tesla, GE, and Vulcan Capital. Sieva had founded StudySoup, a tutoring marketplace serving 5 million students per year, and STK Innovation, a clinical trial marketplace acquired at a significant return for shareholders.

Between them: two serious exits, hundreds of millions in capital raised, and a shared conclusion. The venture capital model – raise, grow at all costs, flip or IPO on someone else's timeline – rewards growth over durability and exits over stewardship. Every business they had built or invested in was ultimately in service of a fund cycle, not a long-term vision. They wanted to build something different.

They met through Summit Series, a network for young entrepreneurs, and stayed in contact for years. When Xavier stepped back from Zola, they asked each other a simple question: what kind of opportunity would make you want to build for 20 or more years? Their answer was a holding company modeled on Berkshire Hathaway. Not a fund with a 10-year clock. Not a private equity (PE) firm charging 2% management fees whether or not investors made money. A permanent C-Corporation that bought great businesses, held them forever, and only won when shareholders won.

The structure is designed around that principle. There are no management fees and no carry. Xavier and Sieva make money the same way investors do – through share value compounding over time. To ensure investors are never locked in, Enduring commits to annual liquidity windows priced at fair market value. The company also commits 60% of free cash flow (after 2025) to share repurchases and commits to buying back shares at fair market value.

They started with friends-and-family capital and personally-guaranteed acquisition loans. UpCounsel was the first deal.

Enduring Ventures' two largest acquisitions in 2023 – Scribe Media and YR, a customization software platform serving Ralph Lauren and other blue-chip brands – were completed entirely with recycled cash flows from existing portfolio companies. 

No new capital raised. No shareholder dilution. This is what the compounding engine looks like when it is working: the portfolio funds its own growth, and every new acquisition compounds the last. Most holding companies talk about permanent capital. This is what it looks like in practice.

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What makes Enduring Ventures genuinely distinct is where they fish. While most acquirers wait for clean businesses at fair prices, Enduring built a repeatable system for buying businesses that are structurally sound but situationally broken.

They call these "special situations." Three categories: VC fallen angels (high-growth startups that burned through capital without achieving venture-scale returns), non-core divestitures (business units that larger companies want to offload), and lender or creditor problems (businesses being dragged down by debt holders that Enduring Ventures can buy out).

The edge is execution. They move in under 30 days. They hold permanent capital with no fund mandate forcing irrational pricing. And they can get creative on structure in ways a traditional buyer cannot – acquiring a brand directly from a bank, closing a carve-out in two weeks, financing acquisitions entirely through recycled portfolio cash flows.

Scribe Media is the clearest example. Scribe had published David Goggins' Can't Hurt Me and was growing fast – until costs outpaced revenue and the bank called the loan. When Enduring arrived for diligence, there was a padlock on the office door. They acquired the brand from the bank, rehired the core team, and relaunched. Within months the business was breaking even on a cash-flow basis. The acquisition was funded entirely with cash recycled from existing portfolio companies. Zero new capital raised. Zero shareholder dilution.

That is the compounding engine in practice.

Today Enduring Ventures owns 25-plus businesses across three distinct playbooks.

Rango Broadband and Snowball Industries – are collections of individually-managed businesses building scale in broadband internet services and HVAC respectively. Both are buying at 3–6x cash flow in industries that trade at 10–25x Earnings Before Interest, Taxes, Depreciation and Amortization (EBITDA) at scale. The multiple arbitrage is the thesis.

The cash cows – led by Dolphin Pools, a top-four pool builder in Arizona with 40+ years of operating history – generate the steady cash flow that funds acquisitions everywhere else in the portfolio. Dolphin had its best year of earnings in history in 2023.

The tech fallen angels – UpCounsel, Scribe Media, Refersion, Abstract, Somewhere – are the businesses nobody else wanted. Acquired at a fraction of intrinsic value, restructured, and compounding.

The result: 25-plus businesses and 400% share price appreciation in the first 24 months.

At Lynnfield, we acquire cash-flowing businesses in the $500K–$5M EBITDA range and offer co-investment opportunities to qualified investors. Join our investor list to receive deal flow as we evaluate new acquisitions. 

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Enduring Ventures and Permanent Equity – which we profiled two editions ago – share the same foundational rejection of traditional private equity. But they represent two distinct expressions of the permanent capital thesis, and it is worth understanding where they differ.

Traditional private equity’s structure creates a mandate to deploy capital, sell companies on a fixed timeline, and raise a larger fund next time regardless of performance. When markets turned in 2022, firms that raised at peak 2021 valuations had no choice but to hold deteriorating assets and hope.

Permanent Equity rejected that model by designing a 30-year fund with zero management fees and carry only triggered on actual cash distributions above a hurdle rate. Their GP only wins when LPs receive real cash. The result: zero pressure to deploy during COVID, and a 29.1% cash-on-cash IRR since 2015 without selling a single company.

Enduring Ventures arrived at the same destination through a different structure. As a C-Corp rather than a fund, there is no timeline at all – permanent is permanent. Zero management fees. Zero carry. Management buys equity at market price alongside investors. And where Permanent Equity waits patiently for clean businesses at fair prices, Enduring goes further: they actively seek the broken situations, the padlocked offices, the startups everyone else gave up on. Higher operational complexity. Higher return targets.

Two firms. Same thesis. 

Thanks for reading!

Xavier and Sieva built the company they wished had bought their own businesses. Inspired by what they’ve done, we apply this same 'stewardship over exits' philosophy at Lynnfield.

We aren't looking for the next moonshot. We're buying businesses that stand the test of time, while we build a durable engine that never stops compounding.

Talk soon,
Param

P.S: In case you’re joining us late, check out the previous editions of this newsletter.