There are a lot of guides and blog posts for founders that provide advice on what to do as a leader of an early-stage startup. But not as many highlight what not to do in those initial days building the next great unicorn.
The tips cover business advice and also general wisdom on taking care of yourself. They include:
- Don’t expect a single deal, hire, or investor to save the day.
- Don’t use work as an escape from home.
- Don’t wait to make hard decisions or deliver bad news.
- Don’t do a bunch of things mediocrely, hoping they’ll add up to greatness.
- Don’t be sedentary.
Winfield received praise online for the list, but got some critical response to a few of the tips. For example, Steven Dunston noted that Winfield’s “don’t hire B talent” tip is “problematic.” Dunston believes those employees can reach greatness but need “a great founder / manager to put them in the right scenario to flourish.”
Winfield responded with: “You don’t have time or structure to ‘put them in the right scenario’ at the earliest stage. You need people who create the right scenario for themselves – or as I would call them, ‘A+ talent.’”
Craig Zingerline challenged a tip on not going broad early, with Winfield advising to “chunk up your rollout.”
“Very early on you have no idea where the growth and customers are going to come from,” Zingerline commented. “From a channel perspective, going broad is almost always smart assuming you have a point of view of intentionality from your user/buyer to help gauge relevant channels.”
Winfield certainly has gone through the ups and downs of startups, both as an operator and now as an investor.
The longtime Seattleite spent nearly 20 years in various leadership positions at four companies — two that went public (Go2Net, Marchex), and two that were acquired (AdXpose, Dwellable).
In 2019 Winfield raised $15 million Ascend’s first round. The Seattle-based firm that invests in Pacific Northwest tech startups at their earliest stage. Ascend has made more than 40 investments over the past two years.
Winfield told GeekWire on Tuesday that most people become founders with zero specific training or experience, and many programs focus on the positive stories of entrepreneurs who “made it.”
“None of these stories address what’s really hard about the zero to one phase, though: just avoiding killing your company or yourself with bad decisions and habits!” he said.
“So I think tips like the ones I shared are important for founders because they remind us to take care of ourselves and focus on the important things we can control, and avoid the most common pitfalls and distractions.”