How do you fundraise through three different recessions?
After selling Cleversafe to IBM for over $1B, serial entrepreneur Chris Gladwin reveals his playbook for raising capital in tough markets, explaining why he pitched over 300 investors for one round and how he’s avoided down rounds by refusing “crazy” valuations.
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
- →Pitched over 300 investors for a single round in a down market, securing 20-30 commitments for a ~10% hit rate.
- →Sold data storage company Cleversafe to IBM for $1.4 billion after raising a total of $100 million.
- →Chris Gladwin has never done a down round, attributing it to avoiding 'crazy' high valuations even in frothy markets.
- →To raise in a recession, your business must be flawless. One Ocient customer cut analysis time by 90% and costs by 80%.
- →Grew MusicNow's top line 20% month-over-month but still had to pursue a sale when the dot-com funding market completely froze.
The full breakdown
Who's on this episode
Chris Gladwin is the Co-Founder and CEO of Ocient, a software company focused on hyperscale data analytics. A serial entrepreneur, Chris has a track record of building and exiting successful tech companies. He previously founded Cleversafe, a data storage company acquired by IBM for over $1.3 billion. His other ventures include MusicNow, one of the first digital music services in the U.S., and Cruise Technologies. Chris began his career in enterprise IT at Martin Marietta and Zenith Data Systems.
Questions answered in this episode
References & resources
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- ·Ocient Official Websitewebsite
- ·IBM to Acquire Cleversafearticle
- ·Circuit City buys MusicNowarticle
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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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