When to Keep Betting: What Every Entrepreneur Should Know
Entrepreneurship is a gamble. At least, that’s how Dawn Verbrigghe sees it.
“I always think of that Kenny Rogers song, ‘You gotta know when to hold ‘em, know when to fold’em, know when to walk away…”
Verbrigghe is no stranger to folding and walking away – she’s currently leading her second entrepreneurial venture. For Dawn, trial, error, and persistence are all part of the long-game of entrepreneurship.
But she’s also no stranger to success. In 2017 she launched Jottful, a service that creates and maintains websites for small businesses. Within a year, she was accepted into the Desai Accelerator program where she closed her first round of funding after pitching at Demo Day. Her customers have been growing since.
Prior to Jottful, she held leadership roles at companies that raised Series A, B, and C rounds of funding. Clearly, Dawn is well-versed in the tenacity necessary for any entrepreneur. However, she’s well-aware some visions don’t become the realities we expect.
For any aspiring or current founders, these four tips are crucial:
Being a founder means going all in
The personal financial impact of entrepreneurship is not always spoken about, but incredibly relevant in the process. Dawn described the draining aspect of keeping a business running. Unlike poker, “Being all in isn’t pulling from some pile of cash, it impacts your own personal finances.”
Folding takes courage, but is important at the right time
Dawn also emphasizes a straight-forward attitude to all entrepreneurs.
“One on hand, entrepreneurship is all about the fight through adversity and finding energy to keep going until something works. On the other hand, you need to know when things actually won’t work anymore. One indicator of this is lost passion. If you dread getting up to work on your business, you should probably quit.”
Verbrigghe does acknowledge the pride of being an entrepreneur, and why failure was hard for her to admit.
“Quitting is the hardest thing to do, because your personal brand becomes wrapped in your company. Walking away from that is incredibly courageous.”
Be a generalist
Speaking on how she and other founders reached success, Dawn emphasizes the generalist skill set required. To her, this broad mindset sets a founder apart from one just focused on product or just focused on selling.
She assures us this skillset doesn’t come naturally, and is something everyone can work on.
“Being a generalist requires working at a bunch of different places and having interests in lots of things. It involves raising your hand and taking jobs outside of your job description.”
Some of these experiences can best be found in later-stage companies.
“If you can experience something further than where you are, you can work backwards to get there at your own venture.”
Be aware nothing happens overnight
When asked about expectation vs. reality moments, the first topic Dawn brought up was the slow pace of work coming to fruition.
“I saw this slow growth in my first business, but was surprised to see it in my second when I thought I had a better idea of how to do things.”
The period of uncertainty is a blessing and a curse.
“Being an entrepreneur is the worst thing ever, “ Verbrigghe said with a laugh, “I would love to be the type that’s happy being the CMO of some large company, but I know I’m not. Entrepreneurship is more of a calling than anything.”
To hear more about the reality of “overnight” success, check out Dawn’s TechTalk here.
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