Passer directement au contenu principal

Article 3 min read

How to overcome self-doubt and thrive through startup challenges with’s Ryan Denehy

The founder and CEO opens up about the challenges of entrepreneurship and how he navigated them to build a successful company.

Par Adam O'Donnell, Sit Down Startup podcast host

Dernière mise à jour December 8, 2023, an IT solution for small businesses, was founded in 2016. Today, has grown to 300 employees, and more than 1000 customers. CEO and founder Ryan Denehy joined us to discuss the importance of overcoming self-doubt, learning how to surrender, and making tough calls. Here are his three tips for other entrepreneurs.

Overcome self-doubt by asking a simple question

Self-doubt can creep in at any time. In Denehy’s case, it first emerged during a time that would normally be a cause for celebration among founders. ‘When the first million hit the company bank account, I was sitting at home one night,” he recalls. “I was thinking of all the different ways the company wouldn’t work, all the potential competitors, and all the reasons why it was going to fail. And I spent half an hour seriously considering just wiring the million dollars back and not doing it.”

Denehy experienced many more moments when he believed was on the brink of failure. Two of them were so extreme that it made the founder physically ill. “It literally felt like my head was detaching from my body,” he says.

Today, Denehy has developed a perspective that has helped him navigate the uncertain nature of being a founder: “What I say is, ‘Well, what’s the worst that could happen? The company fails. I would rather fail having tried than fail after never even starting.’ That’s the thing I remind myself of every day. As an entrepreneur, you have to go into it with the expectation that there is a high likelihood that it’s not going to work, and you just have to get comfortable with it.”

Surrender—only worry about the things you have control over

Over the last 17 years, Denehy has founded three companies. His experience as a prolific founder has taught Denehy not to worry about anything that he does not personally control. He explains, “When people talk about ‘trusting the process,’ that process is having a maniacal focus on the stuff you can control. The stuff you don’t control is going to come at you no matter what.”

By focusing on his own sphere of influence, rather than dwelling on uncontrollable variables, Denehy discovered a newfound peace of mind. “I had to surrender to the fact that I can’t change that we are in a macroeconomic downturn, or that 10 percent of my customers might go out of business,” he says. “You know what I do control? I control my time, how much money we spend, the products we release, how fast we move, and how I communicate with my investors. That was probably the biggest turning point for me in terms of my own sanity—you just need to stop worrying about the things you can’t control. Life gets a lot easier.”

To put his thoughts in order and help him stay motivated, Denehy has developed a habit of writing lists. He says, “It’s like a form of journaling. Every morning I think about the things that are going to have the highest impact. I remind myself of that every single day so that I have my head screwed on straight when I come into the office. I think through the narrative that I would tell internally and externally about how things are going right now.”

Make the tough calls, and know when to say no

After just three months on the market, Denehy was approached by the CTO of a well-funded startup. The CTO offered a $250,000 enterprise deal. “We fell out of our chairs because we were grinding 12 hours a day over $1,000 deals,” Denehy recalls. “Then this really well-known logo comes in and says we will pay you a quarter of a million bucks.”

The deal was tempting. Like most startups, Denehy and his team were fighting for survival. However, after discussing the deal, decided to turn it down because the deal didn’t align with the opportunity the company was pursuing. was created to help small businesses manage their IT, and if Denehy took the deal, he would not only be taking on another customer, but he would also be changing the direction of his business.

“That deal was going to drag us into a highly competitive market where there are a ton of other solutions,” he explains. “It was a tough call to turn the money down, but in hindsight, who knows what would have happened to our company? It would have represented 80 percent of our revenue and 80 percent of our time spent to go build something that ultimately wouldn’t have been a competitive solution in the market.”

Articles associés

4 min read

Achieving that product-market fit moment with Shippo’s founder, Laura Behrens Wu

Discover how Shippo navigated the challenges of customer churn, achieved product-market fit, and raised over $80 million to dominate the e-commerce shipping industry.

5 min read

Finding your product-market fit: Insights from Trulia and Virta Health Founder Sami Inkinen

The entrepreneur explains how he and his co-founder revolutionized real estate, highlighting lessons he learned and strategies for success.

4 min read

From failed startup to finding product-market fit: Thoropass Founder Sam Li shares his journey

The entrepreneur explains how he bounced back and went on to raise $98 million, highlighting lessons he learned along the way and strategies for success.

5 min read

Navigating the peaks and valleys of entrepreneurship: Insights from Redpanda Founder Alex Gallego

In this episode, Redpanda's Alex Gallego embarks on a comprehensive exploration of the entrepreneurial journey.