The Drafting Table
The Drafting Table
Podcast Description
After a decade of investing in enterprise software, I've noticed something fascinating: While everyone talks about becoming a founder someday, almost no one discusses the tactical skills you need to master before making that leap.
That's why I'm launching "The Drafting Table" – a podcast and content series dedicated to uncovering the tactical skills that separate successful operators and founders from those stuck in the dreaming phase.
Podcast Insights
Content Themes
The podcast focuses on tactical skills crucial for successful startups, covering themes like product marketing strategies and operational frameworks. For example, one episode discusses effective product launch strategies with Natalie Marcotullio, highlighting the importance of multi-week campaigns and user-centric messaging. Another episode features David Politis, who emphasizes building an operating rhythm for alignment within startups, addressing the importance of regular team communication and company-wide goals.
After a decade of investing in enterprise software, I’ve noticed something fascinating: While everyone talks about becoming a founder someday, almost no one discusses the tactical skills you need to master before making that leap.
That’s why I’m launching “The Drafting Table” – a podcast and content series dedicated to uncovering the tactical skills that separate successful operators and founders from those stuck in the dreaming phase.
What does it really take to build a fast-growing healthtech startup in one of the most complex industries in the world?
In this episode of The Drafting Table, Jessica Lin sits down with Akash Magoon (Co-founder & CEO of Adonis) and Trey Holterman (Co-founder & CEO of Tennr) to unpack the early journeys of two of NYC’s fastest-growing healthcare startups.
They talk about the brutal reality of finding product-market fit in healthcare, navigating buyer resistance, building through messy integrations, choosing the right go-to-market strategy, and why saying ”yes” too often nearly killed their early momentum.
This is not a highlight reel. It's the real stuff: tough pivots, million-dollar mistakes, and why early-stage execution matters more than perfect strategy.—⏱️ Timestamps00:00 – Intro: Meet the founders and the Work-Bench team
07:12 – Meet Akash (Adonis) and Trey (Tennr)
10:28 – How both founders stumbled into their ideas via personal pain points
12:59 – First-time vs second-time founders: what actually gets easier
14:20 – How they really found product-market fit
17:01 – The danger of building compound products too early
20:22 – Cutting early revenue to focus: painful but necessary
23:43 – Why focus too early can also be a trap
25:06 – Why healthcare integrations are brutal and where founders get it wrong
28:40 – Go-to-market: who pays, how to choose, and landing early customers
30:55 – Pitching ROI when your product replaces headcount
33:00 – Pricing lessons: subscriptions + usage models
36:10 – Selling into healthcare: make it fun, not performative
38:20 – Your first customers should feel like your only customers
40:07 – What they’d do differently starting from scratch
42:10 – Hiring with industry context vs generalists
43:58 – How they manage long sales + implementation cycles
47:07 – Selling to PE-backed provider groups: lessons and myths
49:58 – Moats in healthcare: what actually matters
54:10 – AI in healthtech: team impact and realistic expectations
58:51 – The biggest bets they’re making this year
Subscribe for more conversations like these—#healthtech #startups #productmarketfit #gtmstrategy #venturecapital #workbench #adonis #tennr #b2bsaas #founderstory #startupmistakes #healthcareinnovation #beyondthecore
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