How do you go from a dot-com failure to two successful exits?
After a dot-com bust wiped out his first company, Shane Neman bootstrapped two businesses to successful exits, including an SMS platform he grew to nearly $15M in ARR. Now an active investor, he explains why founders must prove they don't need VC money to attract it and reveals the provocative questions he uses to test their resilience.
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
- →Grew SMS platform EasyTexting to nearly $15M in ARR before its 2013 sale to a strategic buyer.
- →Bootstrapped his second company to over 100 employees and high tens of millions in revenue after his first VC-backed startup failed.
- →Seeded a DTC company that grew from $40k to $4M in ARR in one year after the founder hit the milestones he set.
- →Warns founders that venture is a 12-year game, not 7-10. A 6x paper markup is 'imaginary' until there's liquidity.
- →Tests founders with provocative questions: 'You had two failures before. Why should I believe you won't fail again?'
The full breakdown
Who's on this episode
Shane Neman is a serial entrepreneur and early-stage investor managing his family office, Neman Ventures. After an early venture in the dot-com era, he bootstrapped Joonbug, a vertical SaaS platform for the nightlife industry. Seeing a need for better marketing tools, he then founded Easytexting, a pioneering SMS marketing platform, which he grew to nearly $15M in ARR before its acquisition in 2013. Now based in Miami, Shane invests in early-stage companies and is the author of "Nightlife Lessons," a book detailing his entrepreneurial journey.
Questions answered in this episode
References & resources
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- ·Shane Neman on LinkedInsocial
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- ·EasyTextingCompany
- ·AllermiCompany
- ·Figure AICompany
- ·ApostropheCompany
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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