In 2018, I went through 10,000 Small Businesses. If you’re not familiar, it’s a program sponsored by Goldman Sachs and operated by Babson University that provides training and access to capital for small business owners.

The program covered all the business fundamentals you’d expect: marketing, finances, HR, operations. It was a business accelerator of sorts, with the intention of helping small businesses grow.

A foundational premise of the program was that significant growth was in the new:

  • New markets
  • New products or services
  • New equipment
  • New ways of operating
  • New locations

There was an assumption that we could operate better than we had been, which was why we covered all the business fundamentals. But new opportunities to fuel big growth was what the program, and those fundamentals, were organized around.

Here’s the thing about new endeavors though:

Most of them fail.

Most new initiatives don’t work. Most entrepreneurs chart a path through an ocean of failures. Our successes are like islands in the Pacific.

Predictably, the opportunity I pursued didn’t work out, despite all the research, risk mitigation, and work I invested.

To a large extent though, that’s the game we play. If you want transformational growth, you have to do something very different from where you’re at today. Not a little different, a lot different. And it’s inherently risky.

To quote the print shop worker in Jerry Maguire, “That’s how you become great man… hang your balls out there.” (

I’m not suggesting that entrepreneurship is roulette and you just need to spin the wheel enough times to land on a win. You can mitigate or offset risk. You absolutely should tilt the game to favor success. Just don’t expect it to work.

The silver lining to all this is that while most things fail, they don’t fail completely. That’s why “pivoting” is a thing. When you’re careful in tossing your dart, you probably won’t hit the bullseye, but you’ll rarely miss the board.

But you have to know that’s the game you’re playing and be willing to step up to the line for something new.

Featured image is “Hope and Anchor dart club”, Hope and Anchor, 20 Waterloo Street (now Macbeth Street), Hammersmith, London, UK. c.1925. Used under public domain. The gentleman in the center with the dart board is a “publican.” That’s the technical term for the owner of a tavern, bar, or public house. It’s also an old Roman term for tax collector. New initiatives require more than a bit of courage and a bit of paying your dues.