The Unexpected Habit of Highly Successful Entrepreneurs
Embracing failure openly
I recently had the pleasure of interviewing Jeff, a seasoned entrepreneur and leadership coach, for my new series of Courages Voices in Leadership.
He's a totally fascinating leader with a refreshingly candid perspective on everything from overcoming imposter syndrome to building a thriving online community.
Jeff's willingness to share his own missteps and vulnerabilities makes his insights even more valuable for those navigating the turbulent waters of online writing and entrepreneurship.
In this interview, we delve into Jeff's unconventional journey, exploring the courage it takes to hit "publish," the delicate balance between vulnerability and boundaries, and the power of writing to unlock personal growth.
His advice is both practical and inspiring, delivered with a healthy dose of humor that will resonate with anyone who has ever wrestled with self-doubt or dreamed of making a difference through their words.
So grab a cup of coffee, settle in, and get ready to be challenged and encouraged by Jeff's hard-won wisdom.
Q: Tell us a little bit about your background
I’m assuming you don’t mean what the wall behind me looks like, but just in case, it’s muted white with a red and orange abstract painting that is too complicated for me to describe but, trust me, you’ll like it. I’ve got some great mood lighting going on now which you really have to see to believe. But nobody reading this is going to see it, so let’s just move on to my history.
I’m a recovering entrepreneur. I started my first company at 11 years old, which is an interesting story but I won’t get into that here. As an adult, I’ve started 3 companies, each of which was acquired by a public media conglomerate. After each acquisition, I worked in leadership capacities at the acquiring companies. So I’ve been involved in company growth at every phase of an organization's development cycle.
Over the last couple of years, I’ve focused my time on helping leaders and their teams become more collaborative, highly productive units. I basically teach people how to avoid all the mistakes I’ve made in my past.
I do this through individual coaching, team coaching, fractional leadership, courses, workshops, and keynote speaking. I mostly work with teams at growth-stage and enterprise-level companies.
I’m also a writer, runner, and Ironman triathlete. I like cooking, reading, and short sunrise walks on the beach as long as it’s not too cold.
Q: Beyond the act of hitting "publish," what's the most courageous thing you've done as a writer on Substack?
Ooh, that’s a good question. There are two answers that come to mind.
The first courageous thing was when I decided to launch a paid option to my newsletter. I had about 5,000 free subscribers and believed the Substack hype that 10% of them would become paid subscribers. I was gonna have a good stream of passive income that I could scale.
I soon learned that the paid subscriber hype is just hype. I worked really hard and got less than 100 paid subscribers. After 6 months, I realized that the amount of extra effort required to cater to those 100 people didn’t make sense. So I turned it off after a year and made everything free.
The other courageous thing I do is to continuously try to remain creative and innovative with the articles I write. Sometimes my attempts crash and burn, like this piece of crap where I tried to turn a fairy tale into a parable for Imposter Syndrome:
But sometimes they succeed, like this piece about female leaders that is mostly just a list of facts:
Q: Many people dream of writing but fear of judgment or failure. What advice would you give to those who are hesitant to share their voice on Substack?
Let’s talk about failure first.
Failure on Substack means nobody reads what you write, right? Assuming we agree on that, there’s not much to be scared of.
If a newsletter gets posted on Substack and nobody reads it, did the newsletter even exist in the first place?
If you are walking through your hallway and trip on your own shoelaces but nobody else is in your house to see that, does it really matter?
That’s a rhetorical question.
So if failure is what’s holding you back, I’d say we solved that one.
Let’s go to fear of judgment.
Assuming your desire is for people to read your newsletter, I guarantee you can make that happen. At the very least you can get some family and friends to stop by.
Most likely they probably won’t love what you’re writing at first - but they’ll tell you it’s great. Don’t believe them. Keep working to improve your writing and try to find the right fit for the right readers. There are actually specific steps you can take to do this.
Shameless plug: I put on a workshop called The Secrets To Growing Your Newsletter that you should probably sign up for here:
Which brings us to the fear of judgment.
Judgment always comes with success.
Always.
As Indira Gandhi never said but people claim she did:
First they ignore you
Then they laugh at you
Then they fight you
And then you win
If your writing is being judged, that means people are not ignoring you. They’re reading your newsletter. They can’t judge you unless they pay attention to you, and that’s good news, right?
If you don’t want people to have feelings about what you write, then you should never post on social media or give your opinions on anything.
If you’re being judged (for good or bad) it means you’re doing something that elicits emotions. Mission accomplished.
Not everybody will judge you poorly, but the more popular you get the more you’ll find a smattering of people that will try to bring you down. That’s natural.
But here’s the thing - they are still subscribing and reading!
I once wrote a post about racial discrimination and had a reader contact me and threaten to fly out to Los Angeles and punch me in the face. I’m pretty proud that my words were able to elicit that emotion. I’m also pretty proud that the person never unsubscribed from my newsletter.
The bottom line is that you need to reframe your perception of judgment. It’s not a negative reflection on you, it’s actually a positive reinforcement of the success you’re having.
I probably could’ve said all that in fewer words, yet here we are.
Q: In your opinion, what's the most courageous thing a reader can do after engaging with your work?
I would say the most courageous thing a reader can do after reading my articles is to fly across the country just to punch me in the face.
Probably the other thing is to consciously implement my suggestions for a week or two with an open mind and then tell me what worked and what didn’t.
Q: Vulnerability is often a key component of courage. How do you balance being vulnerable with maintaining healthy boundaries as a writer in such a public space?
I am a fairly authentic person - what you see is what you get. Part of my authenticity is being open and honest with who I am and the things I’ve done.
I talk about my current and previous challenges - like anxiety and Imposter Syndrome - in the hope that it helps people relate to me and lets them know that I understand their struggles. You can see some of that in an article like this:
Or this
Now, I also have a specific voice in my writing and I maintain that voice. The voice is an experienced professional who has a lot of knowledge about business and leadership. But the voice is also somebody who has some self-awareness and is focused on continued personal growth and learning.
So what boundaries do I have? Honestly, as long as it relates to business, leadership and personal growth, I’ll share it. That means there are certain things that aren’t worth sharing just for value sake. For instance, I’ve talked about my wife and our relationship a couple of times, but rarely - because it doesn’t bring value to the purpose of my articles.
I won’t ever mention our daughter’s name or put images of her in my articles - but that’s just for safety.
Q: Courage often involves taking risks. What's the biggest risk you've taken in sharing your writing or building your Substack community?
My biggest risk has been in believing that I have something of value to share (refer to previously mentioned Imposter Syndrome).
The risk has been in believing that I can actually inspire people with my writing and elicit emotions from the readers.
The risk, I suppose, is believing in myself.
Q: What advice would you give to someone who feels stuck or unfulfilled but is hesitant to take the leap and reinvent themselves?
I’m not sure a “reinvention” is needed in order to unstuck oneself. It’s more about self-exploration.
If somebody feels stuck or unfulfilled, one of the best ways out of that maze is to write. It doesn’t matter who you are or what your stuck situation is, writing is magical—even if it’s just a journal.
Remember, you’re not writing for anybody but yourself. But I guarantee that if you write every day - even just for 15 minutes per day - you will start understanding more about yourself and exploring some things that you want to say that are worth sharing.
Keep in mind, the first draft of whatever you put out is probably not going to be liked by others as much as it will be liked by you. That’s ok. That’s expected. The point of writing is to continue down the journey to find your voice and maybe find others who are on the same journey.
There are a lot of people out there who feel stuck or unfulfilled. Simply writing about your experience being stuck has the potential to connect with thousands of people.
Q: If you could go back and tell your pre-Substack self one thing about the journey ahead, what would it be?
Here are a few things I’d tell myself:
Keep articles short. 700 to 1000 words is more than enough.
Start with SEO best practices from the beginning. Once you finally find your voice, it’ll make scaling so much easier. (Hint: See previously mentioned course on the secrets to growing your newsletter
Create a scalable relationship with your readers early on. It’s about more than just a newsletter article every few days.
There are probably a bunch of other lessons, but I’ll remember all of those after this gets published. That way I can beat myself up for not getting them in here.
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’s way of being, subscribe and reach out! He’d love to hear from you.👉 If you enjoy reading this post, feel free to share it with friends! Or feel free to click the ❤️ button on this post so more people can discover it on Substack
Wow if someone threatened to punch me in the face, it would take me a long time to reframe that into appreciation!! And I liked this question “if a Substack doesn’t get read, does it exist?” lol I think so!!
I enjoyed this insightful interview very much and followed Jeff. Thank you for another empowering and inspiring piece on leadership.