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The Drafting Table
Jess Lin
15 episodes
15 hours ago
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.
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Entrepreneurship
Business
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All content for The Drafting Table is the property of Jess Lin and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
Show more...
Entrepreneurship
Business
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What does it really take to build and scale a modern healthcare startup in 2025? | Akash Magoon – CEO and Co-founder of Adonis, Trey Holterman – CEO and Co-founder of Tennr
The Drafting Table
55 minutes 10 seconds
3 months ago
What does it really take to build and scale a modern healthcare startup in 2025? | Akash Magoon – CEO and Co-founder of Adonis, Trey Holterman – CEO and Co-founder of Tennr

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

The Drafting Table
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.