Richard Wolpert | Crain's Los Angeles

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Richard Wolpert


HelloTech offers on-demand and in-home tech support to customers across the nation. The LA-based company was founded by Wolpert in 2014 after a career in tech that includes time with Macintosh and Disney Online.

The Mistake:

We should not have sold [our company]. Had we stayed the course for another five years, we would have probably had the leading address book and calendar that worked on the internet. 

I started my first company in 1987. I was 25 years old and I had just left Apple having been on the Macintosh software team. I moved back to LA and [my] company was called After Hours software. It was a public developer and publisher of Mac consumer software. We ended up having the number one selling address book and we later came out with the number one selling calendar. The company was growing very nicely and we never raised venture capital. It was all bootstrapped.

We got this great offer to sell the company in late 1993 to Adobe. At the time, the internet was really mosaic and just very, very early and starting to take off. I was about 32 and it was a very attractive offer that would make the rest of my life a lot more comfortable financially. So we sold.

So while it was a great exit, it could have been a 10x or more if I had held onto it for another 2-4 years and ridden the wave of that initial internet tsunami that was coming.

The payouts for companies pre-internet and post-internet are just dramatically different.

You have to know getting into the game—it’s a high-risk, high-reward game.

The Lesson:

Startups are very, very hard. There’s a very small number of them that break through to be successful.

So you have to know getting into the game—it’s a high-risk, high-reward game. You need to give it time. It is a roller coaster. And I specifically say on the good days you can’t get over-confident and think that everything’s perfect and you’re going to be a $10 billion company. And equally as important on the bad days, you can’t get depressed and think the company’s going to go out of business.

Prepare for the worst, but hope for the best.

In looking at your business, especially a startup, cash flow is always an issue. Some young entrepreneurs get in trouble when they put together a financial projection. They set up their budget and how much they’re willing to spend, with the assumption that all those things are going to hit and everything’s going to work perfectly. Those are the companies and founders that find themselves getting into trouble because that just doesn’t happen and there will be bumps in the road.


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Photo courtesy of Richard Wolpert