Cool Things Entrepreneurs Do: #stout INSIGHTS from Podcaster Thom Singer

A seminar speaker’s advice to interview 50 successful people to get out of a rut turned into a huge career pivot for this former marketing director. Here’s what Thom Singer has learned about entrepreneurs and success, nearly 350 interviews later.

Thom Singer

Thom Singer, Professional Speaker, Master of Ceremonies,, Business Growth/Leadership Speaker and “Cool Things Entrepreneurs Do” Podcast Host

Thom Singer didn’t start out with the goal of being a podcaster. Four years ago, he was an active blogger, with a popular weekly feature that he called Cool Things My Friends Do. Podcasting was just starting to take off, and Singer decided Cool Things would be the perfect way to test audiowave waters. To broaden interest, he revamped the title to Cool Things Entreprenuers Do, and set modest goal of two interviews a week, for just six months.

A Passion for Podcasting

A hit was born, and Singer recently hit the 345-episode mark for Cool Things, which Inc has named one of the 8 Podcasts Every Entrepreneur Should Follow in 2018. The former corporate marketing director has leveraged his popular podcast into a career as a professional keynote speaker and emcee. He likens the podcast to having his own personal college of professors, interviewing business leaders, entrepreneurs, solopreneurs, and others who possess an extra dose of the entrepreneurial spirit.

In recent months, he has explored topics including running several companies at once, fitness for entrepreneurs, and understanding trends before they happen. Despite their various industries and expertise, Singer has found that his guests all tend to have one thing in common: they are aligned with what they believe, and are true to their purpose and mission. As Thom astutely observes, “If you don’t love it, if you don’t know your purpose, then you’re just going to have your ladder against the wrong wall.” And there’s no need for that, at least according to his guests’ experiences. “What I have found from talking to so  many entrepreneurs,” he shares, “is that there’s a way to make money doing things they can align with. You just have to figure it out – and it might not be the first thing you try.”

“The difference in that valley between potential and results usually comes from taking action and sticking with things.”
– Thom Singer

No One is Truly a “Solo” Entrepreneur

Sure, there is no one else to blame, no fingers to point, when you are in business on your own. But a  critical factor – not only to his guests’ success, but his own – is the support of family and others. Singer admits that he made the cardinal mistake of “sort of springing” his foray into entrepreneurship on his wife. She and his daughters are fully supportive of his work,  but Singer is keenly aware that it’s not what they signed up for, and he is appreciative of their encouragement. It’s also important to share that kind of encouragement with others. Giving back through mentorship is a key part of Singer’s career, and fortunately, he has made some of his best advice available to our Stout readership.

#Stout’s Top-Five Takeaways from Thom Singer:

  1. Move Your Ladder to a Different Wall. Feeling stuck or unfulfilled? Maybe it’s time to try something else. If you are entrenched in corporate life, perhaps you will find your purpose as an entrepreneur. Another option is to change your focus in the workplace – the entrepreneurial path is not for everyone. It’s all about finding your own way.
  2. Don’t Wait to Start. One of the most frequent regrets that Singer hears is waiting to long to actually make a move. That delay does offer the upside of additional wisdom and perspective when you do eventually make a shift. However, starting early gives you a lot more runway to find and fulfill your true purpose.
  3. There is No “Overnight Success”. Singer shares that he expected to his own leap to take about two years, but the reality was more like eight. Don’t be discouraged by a longer-than-expected journey; most “overnight successes” were years in the making.
  4. Surround Yourself with Like Interests. Singer is a big believer in the value of spending time with fellow entrepreneurs in your field. Hanging out, listening to or reading about people doing the types of things you want to do prevents you from having to reinvent the wheel for many things.
  5. Maximize Every Opportunity Given to You. Opportunities to showcase your work are only as good as the number of people who actually see or hear them. Singer encourages his podcast guests to share their interview on their own website and social media channels. Why would you leave your fate only in the hands of others – getting half the return for your initial effort – when you can take an active role in promoting yourself and increasing your exposure?


A “Best Life” Challenge

Singer says that when he turned fifty, he made a commitment that the years between 50-75 were going to be the best of his life, personally and professionally. He is determined to do the things that, for whatever reason, he had talked himself out of doing in the past. This includes a foray into stand-up comedy, and he now has several open-mic nights under his belt. He’s not going to be changing careers anytime soon, but it’s yet another way this entrepreneur’s entrepreneur is pushing boundaries and bringing excellence to what he does. Bold, brave and determined – that’s what being #Stout is all about.

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#Stout BONUS:

We asked Thom to choose his favorite podcast from the Cool Things Entrepreneurs Do archives, and we’ve shared it with you here. For even more inspiration, subscribe to his podcast, and check out our other great coverage on successful entrepreneurs.