Growing the Founding Team — In Plain Language

The everyday-language version of ../business/founding-team-recruitment.md. Andrew is inviting two specific people to help lead WorkWingman. This page explains the offers the way you'd explain them at a kitchen table.

Who's being invited, and to what

David Porter (Andrew's uncle). A career leader in exactly this world: a Harvard PhD in how organizations and people work, a former executive at the Federal Reserve Bank of San Francisco, twelve years running a foundation where he raised over $20 million, and the creator of a leadership program that has graduated more than 2,000 Black executives.

The invitation: come lead this company with me — while keeping everything you already run. The ask is a cofounder seat as Executive Chairman, held permanently alongside his family's real-estate firm and his consulting practice. He never has to give either up. Becoming President full-time is a door he can open whenever he wants — written into the same agreement so nothing gets renegotiated — but it's his option, never a deadline. His ownership stake is the kind reserved for true cofounders, and once the Y Combinator money arrives he also draws a modest monthly salary sized to his hours. The simple guardrails: his family firm says yes in writing, his consulting clients are checked for overlap (if one of them ever becomes a WorkWingman prospect, Andrew handles that sale, not him), and lawyers paper everything. If a cofounder seat is wrong for this season of his life, the same package offers a smaller, honest fallback: a board advisor role with a small stake.

Pamela Morris-Thornton (Andrew's mentor). She has spent thirty years running hiring and people operations — fifteen years at Panera, and today she is the Chief Human Resources Officer of a company with about 70,000 employees. She is, quite literally, the kind of buyer WorkWingman's organization plans are built for.

The invitation: cofounder and Chief People Officer — while keeping her big job. She is not being asked to leave anything: the design lets her hold both seats, permanently if she chooses. Her ownership stake is written down now, but the clock on it only starts counting when two things are both real — WorkWingman getting into Y Combinator with the money wired, AND her company saying yes in writing to her holding the second seat. If her company ever says no, the clock stops. While she holds both jobs she also draws a modest monthly salary from WorkWingman, sized honestly to her hours — but only after the Y Combinator money arrives, only with board approval, and only if her company's written consent expressly covers being paid (if it covers ownership only, she stays ownership-and-expenses until that changes — her employer's rules always win). The full founder salary and a bigger ownership stake switch on automatically only if she ever chooses to go all-in. She never uses anything from her day job here — no information, no people, no relationships — and that wall is permanent and written down. Anything she earns helping as an advisor in the meantime counts toward her cofounder stake. Final terms only become real through signed agreements.

The honest rules both offers follow

• Everything goes through independent lawyers — David is family and Pamela is like family, and the paperwork is what protects those relationships.
• Nobody's name goes on an investor slide without their written permission, and their status is always labeled truthfully: Offered, In discussion, or Advisor.
• A part-time role is never dressed up as a full-time one for investors.
• No announcements until things are actually signed.

The "nothing until the money is real" design

Both invitations are now tied to Y Combinator — the world's most selective startup program (about 1 in 100 teams get in; its graduates include Airbnb, Stripe, and Dropbox, and Sam Altman ran it before founding OpenAI). Getting in comes with $500,000 and instant credibility with every serious investor.

Here's the honest sequence: David and Pamela keep their day jobs — permanently, if they like; neither seat ever requires leaving anything. They'd sign paperwork now only so their seats are ready and waiting. Once WorkWingman is accepted AND the $500,000 has actually arrived (and each person's clearance paperwork is done), their ownership clocks start and each draws a modest monthly salary sized to their hours — David around $4–6k a month for roughly half-time work, Pamela around $2–4.5k for her hours, versus the $8–12k a month a full-time founder draws. The sizing is the honesty: paying part-time people full-time money is what investors flag. The company also pays for the three months in San Francisco. Because Andrew is the only full-time founder unless the others choose otherwise, that's exactly how the team is described to Y Combinator — truthfully. If WorkWingman doesn't get in, nothing changes for either of them — the seats just never switch on, or they can stay involved as advisors instead. Nobody gambles a career on a maybe. One thing that can't be done: paying someone a lump of the investment just for signing up — investors treat that as a giant red flag, and it would sink the application. Salaries, equity, and covered expenses are the honest version.

Why these two

The business plan's biggest money question is answered by organizations — coaches, bootcamps, universities, workforce programs — buying seats for the people they serve. David has spent his career building exactly those institutional relationships. Pamela has spent hers being the person institutions like that answer to. The team slide of our investor deck has one founder and an empty line. These offers are how the line gets filled — honestly.