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.
What 2026 exits actually pay for SaaS
Miro had $600M ARR and 250,000 enterprise customers. They sold for $1.79B — roughly 3x revenue. Their 2021 investors took a 90% haircut on their mark. This is the current market clearing price for quality horizontal SaaS. If you are building toward an exit, you need to know which multiple category your business belongs in — before your board does that math for you.
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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