The Hidden Playbook

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Most people who leave a senior job to start a company assume year one is paid for out of savings, all of it, with no way back. Will Drewery launched his without doing that, and he walked through exactly how.

He spent his career in supply chain and manufacturing at Tesla, Astra, and Mitra Chem, managing billions in capital equipment. At Tesla he sourced the robots, presses, and molding machines that went into the Fremont plant, and the supplier spreadsheet he kept became one of the most important at the company. Years later, after advising former colleagues who had moved on to other hardware companies, he founded Diagon Technologies, an AI-powered procurement platform helping industrial companies build the factories of the future.

His first move was a venture equity program. A VC firm paid him as a contractor for four months to incubate an idea in a space it wanted covered. The firm decided not to invest, and Will left in good standing to build on his own. Then came the bills, and the part he says no playbook covered. Startup law firms that believe a founder is headed for venture funding will often defer their fees until the round closes. His deferred about $20,000 for five months. The cash he did put in went in as a promissory note, a loan to the company with a modest interest rate that he could recover or convert to equity once Diagon was funded.

From there he gets into the raise itself: how every VC pitch call follows the same unspoken structure, why most investors walk in with a 10% ownership target, and why he credits 30% of his $5M raise to experience, 70% to his network, and none of it to the idea. He closes the loop on the upside with the 83(b) election, where he paid $40 for four million founder shares, and the QSBS exclusion, which can make up to $10M of gain tax-free when the company is set up correctly.

He is plain about the limits. Deferred bills still come due, the terms depend on a firm believing you will raise, and the tax moves need a real advisor. But his read is that the gap between founders who know this and founders who don't has very little to do with talent.

Three takeaways from the conversation

Year one does not have to be paid at full price

Will's read is that the firms a founder needs already expect there is no cash in the door. A startup law firm that believes you are headed for venture funding will often carry its fees until you raise, and his carried about $20,000. A VC firm may pay you a contractor wage to incubate first, and your own cash can go in as a loan you get back rather than money you never see again.

Investors fund the founder, not the idea

Will puts 30% of his raise on real-world experience solving the problem and 70% on his network, including former Tesla colleagues he was pitching as customers before he had a product. He leaves zero for the idea itself. In his telling, investors expect the product to change many times before it works, so what they are really backing is whether you are the right person for the problem.

Protect the upside early with 83(b) and QSBS

Will calls the 83(b) election and the QSBS exclusion the two bookends of a founder's tax journey. He filed the 83(b) within his first 30 days, paying $40 for four million shares so his basis was set at the lowest value the company would ever have. QSBS sits at the other end, at the point of sale, and can make up to $10M of gain tax-free when it is set up correctly with the right advisor.

Watch the full conversation

About this guest

Will Drewery is the Founder and CEO of Diagon Technologies, an AI-powered procurement platform helping industrial companies build the factories of the future. He has led supply chain and manufacturing at Tesla, Astra, and Mitra Chem, managing billions in capital equipment, and has raised $5M to build Diagon. He is a board director and advisor to venture-backed startups.

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