How do you fundraise successfully for over 25 years?
After raising capital every year since 1998 for a total of over $250M, serial entrepreneur Nick Desai explains why fundraising is a constant process and why he once risked his company by rejecting a lowball term sheet to wait six months for a $100M strategic investment from Humana.
Highlights
- →Endured a 6-month due diligence process for a $100M strategic investment from Humana, two years before they acquired the company.
- →Rejected a 'lowball' VC term sheet to bet on a strategic partner, risking the company while waiting 6 months for Humana's diligence to close.
- →Learned a hard lesson in the dot-com boom by not forcing a sale at the peak, a decision he now calls a 'stupid mistake.'
- →Prioritizes clean terms and board control over chasing the highest valuation, stating, 'The only valuation that matters is your last one.'
- →His corporate lawyer of 20 years called one investor's documents 'perfect' with zero comments—the hallmark of a credible partner.
The full breakdown
Who's on this episode
Nick Desai is a serial entrepreneur with a track record of building and exiting companies in the health tech sector, having raised over $250 million in capital since 1998. He is the co-founder and CEO of Together by Renee, an AI-powered health assistant for aging individuals and their caregivers. Previously, Nick co-founded and served as CEO of Heal, a pioneering doctor house-call platform that raised over $200 million from investors including Humana and Fidelity before being acquired by Humana. His entrepreneurial journey began in the dot-com era, providing him with extensive experience in fundraising and navigating multiple economic cycles.
Questions answered in this episode
References & resources
- ·Nick Desai on LinkedInsocial
- ·Nick Desai on Xsocial
- ·Together by Reneewebsite
- ·HealCompany
- ·HumanaCompany
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- ·Pi CapitalCompany
- ·Queue, Inc.Company
- ·Montgomery Summitother
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Hosted by

Podcast host, angel investor, and serial entrepreneur with 4× exits ranging from small businesses to VC-backed tech companies. Jason has been personally involved in over $100M in transactions and now helps founders close their next transaction at Thunder.vc, from pre-seed rounds to $100M exits. He coaches founders through their next major transaction and gets the deal done by introducing them to the right people in his network.
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