Jun 15, 2022 · 28m · product-market-fit
How to Build a Board of Advisors | Darryl Hicks, Founder of Flexpay · PMF Show
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Product Market Fit Show, Flexpay co-founder and CEO Darryl Hicks breaks down his framework for building a world-class advisory board prior to generating revenue. He explains how recruiting active, in-the-trenches executives across key operational skill buckets provides early-stage startups with critical shortcuts, top-tier network introductions, and governance playbooks.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Pablo holds 22% of the talking time here. How this is scored →
speaking balance: gold is Pablo, purple is the guest (3 minute bins)
Darryl firmly dismisses the conventional practice of hiring semi-retired board professionals, insisting on active operators executing in the trenches.
Hardest push from Pablo ▶ 4:03 Challenging the arbitrary eight-bucket numberPablo pushes back on Darryl's framework, asking why it must be eight instead of six or ten.
Biggest teaching moment ▶ 21:50 Masterclass on courting advisorsDarryl educates listeners and the host on outreach psychology: asking directly for an advisor role blows up the deal, whereas asking for advice leads them to ask how they can help.
Pablo holds their own ▶ 18:33 Pablo shares Gymtrack vetting war storyPablo demonstrates startup operating acumen by recounting an advisor from his Gymtrack days who only had one hour of real insight, pressing Darryl on how to vet depth.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Pablo as informed peer | Guest teaching | Guest disagreement | Pablo pushing back | Why |
|---|---|---|---|---|---|---|
| The 8-Bucket Framework for Building an Advisory Board | 2 | 5 | 1 | 2 | Pablo prompts Darryl to explain why he opted for a formal advisory board, then lightly challenges the exact number of advisory buckets. Darryl explains Dan Martell's 8-bucket framework and the psychological power of constraints. | |
| Identifying Skill Buckets, Finding Talent, and Advisor Value | 1 | 5 | 0 | 0 | Darryl lays out his framework for selecting advisor skill buckets and outlines the operating rule that advisors provide conversations, strategy, and connections rather than execution. | |
| Formal vs. Informal Advisors and Trench-Executing Talent | 2 | 4 | 1 | 1 | Pablo asks how Darryl knew when to formalize relationships with equity and how he crowdsourced advisor recommendations at Money20/20. | |
| Advisor Roles, Super-Connectors, and Call Preparation | 3 | 3 | 1 | 2 | Pablo probes why Darryl avoided scheduled recurring board meetings. Darryl explains that demanding calendar commitments scares away top in-the-trenches talent, opting instead for ad hoc 'bat phone' calls. | |
| Advisory Board vs. Investor Sounding Boards and Vetting | 4 | 2 | 0 | 1 | Pablo brings in his own startup founder background at Gymtrack to ask how to vet advisors who only possess one hour of useful depth. Darryl clarifies that filtering strictly for active operators solves this problem. | |
| Advisor Equity Compensation and Outreach Strategy | 2 | 5 | 0 | 0 | Darryl breaks down standard advisor equity grant percentages (0.1% to 1%, typically 0.2%) and explains the outreach strategy of asking for advice rather than an advisory role. | |
| Real-World Advisory Impact: Playbooks, Intros, and M&A | 2 | 3 | 0 | 1 | Pablo asks about advisor churn and sunsetting. Darryl explains how advisors provided playbooks, opened doors at Stripe, and how he filled his open 8th seat with an M&A specialist. |