Taking the Leap Into Entrepreneurship

Taking the Leap Into Entrepreneurship

Kathy Leake, Co-Founder/CEO, Crux Intelligence

As RECODE data reporter Rani Molla wrote recently: “The so-called Great Resignation is going strong, and it’s not just for working stiffs anymore. Increasingly, managers are also leaving their jobs for greener pastures.“ 

Perhaps those managers are not looking elsewhere for a paycheck, but deciding it’s now or never on that entrepreneurial dream? As NPR noted “The Census Bureau found that a whopping 5.4 million new business applications were filed in 2021, surpassing the record set in 2020 of 4.4 million.” 

In case you’re sitting in your corner office staring at the horizon, wondering if you have the guts to quit and do your own thing, here’s what I learned after leaving corporate America in pursuit of the start-up scene. 


Start planning while you’re still employed. It’ll take the pressure off. Just don’t do it in your office, during work hours, or using your employer’s equipment (or Cloud-based storage). If you have a number of ideas, use your network to parallel track, do research, and validate a need. Once you’ve got confidence in a particular direction, let go of what isn’t viable and continue to refine your concept.  

A word of caution. At this stage, pick who you confide in very carefully. Those who are close to you (especially those who are dependent on you financially, emotionally, or otherwise) are going to be risk averse, to say the least. Pick neutral, but informed, highly experienced, and smart people in your network. I have a very close knit inner circle of mutual “cheerleaders” and they’re my lifeline, and I’m theirs. 

You have to be willing to face your fears and keep going. Trust your internal compass. No matter what society has “told me to be” I’ve done my own thing – and never regretted it. 


It’s often said that starting a business with a co-founder is like a marriage. Choose wisely. If you have to “decouple” later, it’ll be painful – so get everything nailed down contractually from day one. 

I’m fastidious about vetting people, and I hope that others do the same with me. I want to know I’m working with people who operate with integrity and that we’re working towards the same vision, and goals. If you see a red flag, don’t ignore it. 

Hiring is a heavy responsibility for an entrepreneur. People’s rent/mortgages, school fees/vacation plans rely on you making payroll every month. They’ll be taking a huge risk on you, and your abilities. Recruit risk-takers, proven deliverers (not fast talkers), and those with a curiosity-based mindset, especially people who want to do their own start-ups next, and are looking to learn.   

This might sound counterintuitive, but be careful with anyone who worked for the FAANG (Facebook, Apple, Google etc) companies. Those firms denote pedigree, sure. But they give workers so much support, right down to the city-to-suburb shuttle, in-house canteen, snack bars and pre-formatted presentation decks for conformity. To ensure you’re getting a self-starter, ask candidates to tell you about how they developed a new idea from scratch. Then fact-check their story to ensure they did it all. 

I’m loath to hire anyone who never had to work because they were supported by their parents. Bring me people who survived a year of Saturday night shifts in the busiest restaurant in town, while maintaining a 4.0 GPA, and launched a start-up in their dorm room with real revenues. That takes stamina, smart thinking, grit, determination, and skill.    


This is really tough. Get strategic to acquire the science behind the mindset. I met with lots of VCs and asked them: “How many minutes into a Founder’s pitch before you decide whether to move forward?” Three minutes was the consensus. 

That completely changed my pitch. I front-loaded the deck with whatever I knew would convince them – about me, the technology, the concept, the deal. I asked VCs about their favorite entrepreneurs, why they invested in them, how they communicated with them, what kind of reporting they wanted to see, what were the pain points and how did they overcome them. In subsequent rounds all this research helped me enormously. Plus I delivered on their investment. That’s what VCs are looking for in the end. 

I never waste my time chasing anyone. If a VC isn’t getting back to you, they’re not interested. Move on, and find the people who believe in you. 


Entrepreneurs need a thick skin and unbelievable stamina. It’s lonely and it’s tough. Everyone needs someone to talk to. Paying for wise counsel is a good idea. All the top people have a corporate coach. There’s a reason why the field is worth $14 trillion in the USA. If you want to stay sane, don’t dump on your spouse, or moan to your former colleagues at the cushy corporate job (they’ll just tell you to call HR and go back to the corporate grind.) 

Get the stress out of your body. Upgrade your sneakers and go for a run. Buy a punch bag, learn to kick-box, swim lengths before dawn, book a weekly massage, get a weekend bolthole and/or learn how to meditate. 


Is it all worth it? Oh, yes. Even the bad stuff? Definitely. I’ve learned from every mistake. There’s no such thing as failure. Failure is not an option. I have pivoted and regrouped and done what it takes over and over again. You’ll never know how good you are until you try. 

Being an entrepreneur has given me some of the most incredible moments in my life. I have zero regrets. If you try it, I wish you all the luck in the world.  


Alternative Text Kathy Leake
CEO of Crux Intelligence and four-time founder/board member. Putting AI in the hands of every business user.