How Do You Build Confidence As An Entrepreneur?


“We’re upping our plan for the year,” “James,” the CEO of a very successful startup I’m working with said to me. It was the second time he’d increased his plan in the past six months.

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“Cool,” I said. “You’ve finally entered what I call ‘turn the crank’ mode. The flywheel is turning at a really good pace. “

“Yes, it is,” he said. “I think revenue is going to double to over $20 million this year.”

“That’s fantastic,” I said. “How’s the team feeling?”

“They’re really pumped up,” James said.

“I’ll bet they are!” I said.


You build confidence and momentum by meeting and exceeding your plan.


When I started working with James a few years ago, revenue was at $1 million. One of the first thing James did was set up monthly revenue goals to hit.

He made the goals visible for everyone in the company to see. At first, the changes in the goals were small. From a $100,000 monthly goal, to a $110,000 monthly goal, to a $120,000 monthly goal, the numbers steadily increased.

Ninety percent of the time, James and his team were exceeding their goals. That’s pretty good performance, especially from a startup.


Then, you continue gaining confidence when you meet and exceed your plan again and again.


“You know, it felt like we were pushing a boulder uphill in those early days,” James said. “But each time we met our goal for the month, it seemed to get easier and easier.

“Now, it’s just amazing to look back and see the progress we’re making. $1 million a month now! And we’re not even close to being done. We’ll be at $2 million (a month) by the end of the year.”

“I know,” I said. “You guys are doing great. What’s the feeling that the team has?”

“That they’re unstoppable,” James said.


Make sure to celebrate your successes along your journey.


Each time James’ team exceeded their goals, James had some sort of reward for the team. It might be a Starbucks gift card for everyone, or maybe movie tickets for the small goals.  Whatever goal they hit, there was always a reward of sorts.

James was going to have a big party when they hit $10 million, but COVID-19 got in the way. Instead, the team has agreed to have the party when they hit $20 million at the end of this year.


Finally, never be satisfied with where you’re at.


“Now that you’re at $10 million moving to $20 million, it’s time to think about the company at $100 million,” I said. “What does the team look like? What positions do you need to fill? What technology do you need? What competitive threats are out there? You’ve done it before.”

It’s a planning exercise James and I have gone through every year, and it’s one I highly recommend you go through as well. The exercise forces you to take a hard look at the challenges your company will face as it scales to 10X its current size.

“I’m planning on having my team start working on it (the planning exercise) at the beginning of next month,” James said. “I think they know what to do since they’ve been through it before.”

“That’s great,” I said. “I can’t wait to hear the results.”

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