Shipt founder Bill Smith discusses selling his second business, prepaid card company Insight, to public fintech company Green Dot.
What-if
Bill Smith: Shipt and Landing would have failed if launched two years later
“The timing of everything that I created, if you just rolled it forward two years, it wouldn't have worked. In, InSight wouldn't have worked. Shipt would have missed, completely missed the window. Even landing, we would have missed the window because there's ju…”
Disclosure
Graycroft pushed Smith to consider not selling Shipt to Target
“My partner there really pushed me to consider not selling. He said, look, I'm going to do whatever you want to do. I mean, you're the CEO and, you know, whatever you want to do, we're with you.”
Assertion Not checkable as stated
Smith personally wired funds to cover Shipt payroll before Series B
“So I remember we were working on closing the B And we literally ran out of money to make payroll, and I had to fund it, you know, personally. I had to wire money in from my own bank account to cover payroll to get us through.”
Insight
Smith: Absorbing acquired startups and stripping their identity often leads to failure
“Some companies can do an acquisition, and they will absorb the company they're acquiring, and integrate it in, and you kind of lose your identity, and a lot of times these acquisitions become failed acquisitions.”
Assertion Supported
Smith: Target acquired Shipt in an all-cash deal exceeding $550M
“Five hundred and fifty million dollars is actually a little more than that. That was on the table and an all cash deal.”
Insight
Smith: Daydreaming about payouts distracts founders and kills acquisition deals
“Whenever I've sold a business, they never happen fast. It is very easy to get distracted and excited and thinking about what you're going to do with your millions. But if you take your eye off the ball, And the numbers turn or something changes. It's game over…”