80 Founders Share The Moment They Knew … When They Really Had Something


I recently asked on Twitter when folks knew their startup had something … great.

Because as a SaaS founder especially, it can be hard to know.  Hard to see when you can’t be killed.  Hard to see when your brand is coming into its own.  I asked Todd McKinnon, founder-CEO of Okta when he really knew he had something that couldn’t be stopped, and he said $30m-$40m ARR!

I really only knew as we approached $10m ARR.  But looking back, really, I should have known much earlier.  I should have known in fact when I spoke at an event with 4 leading tech companies … and all 4 talked about how they used Adobe Sign / EchoSign.  I didn’t know then, but I should have.

So let’s look at what 80 founders and CEOs shared!  Some of my favorites:

“When a customer sent a note that said, I know it’s free, but I think what your doing is amazing and I want to support you guys, so she paid us anyway.”  — Jason Riedel, founder/CTO of Aspireship

“When on New Year’s Eve, customers kept sending us signed contracts.” — Sanjay Singh, co-Founder GlobalLogic, co-Founder CEO hCentive

“When we had 1 in 5 people using our products across cafes. 20% conversion.” — Safia Qureshi, Founder & CEO of CupClub

When we got invited to a customers wedding in Germany because they said our happiness course changed their life and saved their relationship….or maybe a note from another lady who said the only way we could be better was to serve her free wine & chocolate with the course” — Chris Rawlinson, Founder 42 Courses

When people started landing their first tech jobs.  Genuinely life-changing” — Helen Huang, GitHub

“The moment (3) healthcare execs left jobs paying them $300-$500K salaries…” — Aron Shea Placenica, founder, Superhuman.health

“When a professional athlete inquired about a partnership” — David Goldberg, founder, Freshneck

“When customers get back $100k’s in minutes and want to pay us more” — Kanat Bekt, founder/CTO, SupplyPike

“When a Microsoft Gold Partner told us to white label our product during the demonstration.” — Albery Anthony, Founder, Loves.Cloud

“When my first meeting with a major college athletic department scheduled for 30 minutes went on for 2.5 hours with additional people invited to brainstorm various uses.” — Drew Naugher

“When the big customer reaches out to you before you reach out to them.” — Marty Ringlein, Brex

“Apple wanted to talk to us” — SF Nocode – Lowcode

“A customer who tested the product and did a glowing user interview… then called me back to give more feedback” — Jason Weingarten, CEO/founder Yello

“When an enterprise customer told us that after using our platform he has 4 people that are free to do other things because we automated their day today!” — Lonny Szneiberg, Olachau

“When we were invited to the White House.” — Ran Korber, Founder, Breezometer

“When an enterprise customer told us that after using our platform he has 4 people that are free to do other things because we automated their day to day!” — Lonny Szneiberg, founder Investing.com

When I had a celebrity customer and got approached by BritishVogue” — Zibeauty 


“When my dream investor, agreed to join the ride. :)” — Cedic Bollag, Founder, GlobalTechBox

“Our customers represented ~55% of our seed round!” — Ameet Mehta, Co-founder, Syndication Pro

“When (in bootstrap mode), our prediction algorithm for music outperformed the algorithm that won Netflix’s $1m prize for movie predictions.” — Ryan O’Leary, ListenUpBeat

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