From Freemium to Premium with Matthew @ Yesware.com - Escape Velocity Show #28

About this video

Dan Martell interviews Matthew Bellows, founder of Yesware and now of BodesWell, described as his third greenfield startup. Bellows says BodesWell is a planning tool — ’like a telescope’ — for ‘mass affluent’ Gen X users asking whether they can afford college, a parent’s long-term care, a lake house, travel, or retiring at 50; it was in closed beta with the business model (B2C, B2B, B2B2C) still undecided. On Yesware, he says it raised $50 million, began as a Chrome extension, and grew via the Chrome store from 10 to 1,000 users a day and, he claims, 10,000 free users a month. He says email tracking — not the templates feature built first — produced the ‘glint in the eye’ magic moment within 10-15 seconds. He recounts the first sale came after about five to six months when Ben Sardella asked to be invoiced (about $5, later $10, now $15 tiers), and that ending freemium around 2014-15, after over 100,000 free users were not converting, produced their best revenue month ever. His pitch was that 1 in 10 workers is a salesperson using generic tools, so software for the end-user salesperson would make them money and they would pay. He advises bootstrapping toward $10-15 million ARR before non-dilutive or growth capital, cites Brad Feld’s ‘slow down to speed up,’ pinning one specific core customer (‘Dave’) for BodesWell, and describes 25 years of sitting meditation, including a three-month retreat meditating about 12 hours a day.

Key takeaways

• Test for the ‘glint in the eye’ within 10-15 seconds; email tracking, not templates, was Yesware’s magic moment
• Chrome store distribution drove Yesware from 10 to 1,000 users a day, per Bellows
• Ending freemium after 100,000+ non-converting free users produced the best revenue month, he claims
• Build for one specific core customer persona instead of a broad horizontal market
• Bellows advises bootstrapping to $10-15M ARR before taking growth or debt capital

Episode details: published May 21, 2020 · 42:38 long. Summary written by Self Growth Videos from the episode itself. Business results and any income figures mentioned are Dan Martell’s own claims, shared for education — they are not typical or guaranteed.

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