Investing In Yourself With Cheryl Contee Of Do Big Things

Today we’re talking to Cheryl Contee, the Chief Innovation Officer at The Impact Seat, and the co-founder of Do Big Things. While attending Yale, Cheryl was a struggling minority scholarship student that was required to do work study while enrolled.  She says the highest paying job option was in the kitchen at $17/hour, with the next highest paying job being at the help desk for $8/hour.  Cheryl not only couldn’t see herself doing dishes day in and day out, but she knew taking that pay cut would allow her to learn a lot more.  She says she learned so much about technology and customer service that she knew it was the right decision. If the willingness to learn is there, you should always invest in yourself.

Know Your Worth

After her time at Yale, Cheryl was recruited by a large PR firm.  Within her offer letter it said that, with decent performance, she would be promoted.  Cheryl said she found herself working 18 hours a day with no talks of a promotion.   She told the company that if they would just hire 3 more people and do certain things, she could get them to a million in revenue.  The company laughed at her, and still no promotion.  Cheryl knew it was time for her to move on and go somewhere she was appreciated.  She sent out a tweet to everyone she knew letting them know she was available and asking who wanted to work with her.  She ended up getting together with a friend’s wife and quickly grew a digital agency to a million in revenue.

An Untapped Industry

Cheryl says that with her feet in a few different worlds, she could see what was happening on the corporate marketing side and that there was no tool like that for the nonprofit sector.  The nonprofit sector is an 8 billion dollar industry per year, so it made sense to tailor that type of software to nonprofits, campaigns, etc.  Cheryl knew it could be a really powerful tool to help them unlock greater success.  They bootstrapped the idea internally for 18 months before they realized that it needed outside capital, and its team.  She says they were lucky to get funded and that it took a year to raise that first seed round.  The KPIs they found themselves watching during this time were mainly in renewals.  They wanted to know how many people were sticking around and re-upping an annual subscription.  They found they had to invest more in customer service and help to make sure people were on-boarding successfully.

Starting With The End In Mind

As a believer in planning for an exit when you first start a company, Cheryl says they did just that.  They had a strong sense that this was the type of product to be acquired.  This decision caused them to be more thoughtful and strategic about their partnerships and marketing.  Cheryl finds herself mentoring many startups now and always tells them the same thing; plan for the end from the beginning.  Cheryl knew it was time to sell when they felt the winds of change.  She knew they could either raise another round or start the process to sell.  They decided that, based on the environmental factors, it was time to sell.  Cheryl says they reached out to and interviewed many bankers.  She says they knew what they didn’t know, and that was how to negotiate, so it was vital to get a great banker.  The one they chose created a grid of different sectors and companies that could be interested in them, many that Cheryl never would have considered.  Overall, it was one of the strategic partnerships that they had that bought them. Cheryl says many people make the mistake of looking at their business as their baby.  It’s hard to think about selling your baby.  She says it’s better to think of it as a house.  A house is an investment that you love, but usually someday you plan to recoup on it.  When you look at it that way, you will be more objective on where you stand.

Her Most Important Startup To Date

The acquisition took place in July 2015 and in August 2015 Cheryl’s son was born.  She jokes that he’s her new startup, he has a 20-year runway, and there’s no exit strategy yet.  All jokes aside, she still had another company going at the time.  Through a few mergers, that company became known to Do Big Things.  In addition to Do Big Things, Cheryl is currently working at The Impact Seat as the Chief Innovation Officer.  The Impact Seat helps to develop female startups with a diverse-led firm.  As the Nasdaq requires a diverse board if you want to be traded, studies back this up showing that diverse led firms are more innovative, productive, and profitable.

Knowing What You Know Now

What Would You Tell Yourself Ten Years Ago?

Between climate change, shaky political systems, and COVID-19, Cheryl says to map your business strategy to the world you see coming.  Try to be as forward-thinking as you can because things are going to always change.  She also would tell herself to trust in herself and follow her instincts.  Neuroscience tells us that intuition comes from the smartest part of your brain trying to communicate with you.

Where To Learn More

Cheryl is working on the second edition of her book, Mechanical Bull: How You Can Achieve Your Startup Success. She calls it the book she wishes she had when she was starting out.  The book goes through the full life cycle of a startup and the new edition will have a preface that talks about current times.  The audiobook version will be out later this year and available on Amazon.


Steve McGarry

An entrepreneur, content creator, and investor based in sunny Tampa, Florida. In 2015, while living in San Francisco, Steve sold his first fintech startup LendLayer to Max Levchin’s (founder of PayPal) consumer finance company Affirm.

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