Jessica Markowitz: A 25-Month Partnered Search That Ended in a Bay Area Legal Services Buy

The Setup Jessica Markowitz finished her MBA at Chicago Booth without a legal background and without a solo mandate to go buy something. She teamed up with Trista Engel, and the two spent six months stress-testing whether they should actually run a company together before they ever wrote a single LOI. They used partnership books, a written charter, scenario planning, work-style exercises, and peer reviews. That upfront work set the tone for everything that followed. Their target profile was deliberately narrow: a B2B service business in a fast-growing industry, minimum $2M of EBITDA, margins above 15%. Not a distressed turnaround. Not a trades roll-up. Something with recurring client relationships they could grow without needing to be the technical expert in the room. The Deal The search took 25 months. The funnel was enormous: - ~40 interns cycled through sourcing work - 9,000 companies contacted on the proprietary side - 8,000 brokers contacted on the intermediated side - 500 phone conversations - 60 in-person business visits - 20 LOIs submitted, split roughly 50/50 proprietary vs. broker-sourced The winner was Paragon Legal, a Bay Area firm placing interim in-house counsel inside corporate legal departments. Closed August 2018. Neither partner was a lawyer, which scared them going in and scared the seller too. They neutralized that risk by keeping the founder attached as an investor and board advisor post-close. She became the credibility bridge. One nonobvious stat from the search: three of their ten proprietary offers came from referrals generated by owners who had initially said no. Not-for-sale is a starting position, not a final answer, if the outreach earns trust. First 100 Days The transition risks they feared showed up. A key internal team member left shortly after close. The business kept running anyway, because: - The founder stayed visible to clients and attorneys as an investor/advisor - Existing clients and the attorney network got explicit continuity signals - Neither Jessica nor Trista tried to impose a legal-operator identity they did not have; they ran it as operators of a service business Zero clients churned during the handoff. Zero attorneys on the placement bench walked. For a people-business built on relationships with both sides of the marketplace, that is the number that matters. Operating Moves Year one client additions: 40 new corporate clients. The prior cumulative client count was 27. They more than doubled the active client base in twelve months. The lever was not a new product. It was sales capacity and process applied to a founder-run book that had been growth-constrained by the founder's personal bandwidth. The macro tailwind helped. Corporate legal departments were getting squeezed on budget, which made flexible interim counsel more attractive than permanent hires or full BigLaw engagements. COVID-19 later accelerated that shift. Operating Lessons