How Much Are You Willing To Bet On Yourself?

Small business owners need to bet on themselves.

“We were betting on ourselves,” Jeff Ullrich, co-founder of Earwolf and founder of Midroll, explained.

He had taken his wife’s Roth IRA and invested the whole of it (about $30k) in starting a company with no guarantee of success.

He wasn’t betting on the market. Earwolf was a podcasting company before podcasting companies were a thing. There was no market.

He wasn’t betting on his track record as a business owner. He was a washed-up, alcoholic manager to B-level talent. He had no track record.

He wasn’t betting on a proven business model. He couldn’t follow any blueprint for raking in cash because podcasts just weren’t making much money at the time. There was no proven business model.

The only thing he and his business partner could bet on was their own ability to persevere, overcome, and figure it all out––largely because there was nothing to fall back on.

I was out for a walk this morning when I heard Jeff say, “We were betting on ourselves,” on Arlan Hamilton’s podcast Your First Million. And it stopped me in my tracks. Hat tip to Jacquette Timmons for the podcast suggestion!

“We were betting on ourselves,” struck me because, for so many of us––myself included, we’re so quick to bet on anything other than ourselves.

We’ll bet on someone’s proven 6-figure online course formula. We’ll bet on the global reach we can get through Facebook or Instagram. We’ll bet on getting found in search on YouTube. We’ll bet on meeting the exact right person at a conference. Or, we’ll bet on getting featured on a great podcast or news outlet.

What I heard Jeff say, though, was that he was willing to bet on his own ability to get stuff done. To make it happen. To find what works one step at a time and build on it.

Amy Hoy writes, “Success is, by definition, figuring out what works and doing it over and over again… Keep doing it until it stops working. Which, by the way, it almost never will.”

Building a business that works isn’t about placing a bet on something novel, innovative, or trending.

It’s betting that, no matter what the path to success is going to be, you will find that path by doing the simple, small, boring work.

We’re getting to that time when we decide what to bet on in the new year. Maybe you have your sights set on a new product. Or maybe you’re eyeing a new marketing strategy. Maybe you’re making an investment in a new coach or course.

Whatever you decide to commit to next year, remember to bet on yourself first.

With gratitude,

Tara McMullin
Founder, What Works


Over 8 years ago, Rebecca Ching signed a commercial lease on the space where she would make her dream into reality. But the stars in her eyes quickly faded as she realized how misguided her initial expectations for her business were. I asked her about the mistakes she made, what she learned from them, and how she’s doing things very differently today.

🎧 Click here to listen.


I loved Jeff Ullrich’s conversation with Arlan Hamilton–a venture capitalist who’s made waves prioritizing investing in women, people of color, and LGBTQ founders. Jeff speaks very humbly about what he created and how he did it–while making the point that a huge part of his success was being willing to continue better on himself by reinvesting almost every penny back into the business as they grew. He also shares how much reflection he’s done on the privilege he has benefitted from along the way.

🎧 Click here to listen.


You might have heard me say, “People don’t buy drills, they buy holes,” before–paraphrasing marketing professor Theodore Levitt. But what if they’re not even buying a hole? What if they’re buying the image of themselves as a competent DIYer? The kind of person who spiffs up their own house on the weekends? What we buy–and how we sell the things we sell–is so much more that talking about your product or service. This article explains a unique way to think about it.

👓 Click here to read.


Most sexy headlines are about how to write a bestseller or how to launch a hit product. But what if the real key to creating great things was to create a lot of “just fine” things? I’ve long admired my friend Srinivas Rao’s ability to crank out good work every single day. Not all of it is a hit (although he’s had plenty) but all of it is good and moves his message ahead. He’s just released a completely free (no email address required) ebook on how to become prolific.

👓 Click here to read.


I’ll be sitting down with Marie Poulin to take you behind-the-scenes of how the What Works team manages our full editorial calendar––podcast, community events, member contributions, communication, this newsletter, and more––on Friday, November 8 at 1pm Eastern/10am Pacific. Join us!

🎥 Click here to register.

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Cover of What Works book by Tara McMullin

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