Dave Will is an entrepreneur, but hasn’t always been one. He is cofounder and CEO of Prop Fuel, a platform that helps associations take action on member feedback. He is also the host of the Entrepreneurs’ Organization Podcast, EO360.
He started his career with venerable companies like PWC, Kraft, and Nielsen. But, he was doing just fine. He lacked urgency. He got fired.
Enter entrepreneurship. Dave built a successful company and exited. He jumped into new pursuits like hosting podcasts. He interviewed television adventurer, Bear Grylls. He learned to manage intimidation, embrace radical candor, and set aside time to think.
Listen to the full episode. You’re sure to pick up a nugget or three.
Don’t have time on your commute to work? Skim the top five themes below. Then listen to the full episode on your commute home.
5 Core Themes
Here are five themes you should take note of in your own career adventures.
Be Intimidated
Remember to do things that are intimidating. It’s easy to get comfortable. We grow when we step out of our comfort zone and into a new space.
Dave interviewed Bear Grylls once at an Entrepreneurs’ Organization event. Bear Grylls is a survival expert and adventurist well known for his work in the television show Man vs. Wild. Before interviewing Bear, Dave was intimidated. He was about to be on stage in front of thousands of attendees. Yet, he leaned into his strengths and previous experiences to manage his fear. He excelled. It was a great experience.
“I don't think I slept for the next two nights until I interviewed him. The interesting thing is even though I was really nervous leading up to it, I've done so many interviews. As soon as my foot hit the stage, all the fear went away, which you would think it would get worse, like you would think walking up a stage lights all the people like that would make it worse. But I think instantly I was just in my comfort zone because I'm so used to actually doing the interviews with people. It's like finally I get to actually just sit and have a conversation and ask him questions.”
How can you pair strength with fear to grow your career?
Just Jump into Opportunities
Dave runs the Entrepreneurs’ Organization podcast, EO 360. About a decade ago he started it. He didn’t know anything about podcasts at the time. All he knew was that virtual learning webinars were going the way of the Dodo and being eliminated with the EO. As an EO member, he found the virtual learning series to be valuable. He saw an opportunity to keep virtual learning alive just with a different medium: the podcast.
Jumping into the opportunity helped grow his career. He’s learned from thousands of people. He’s likely helped tens of thousands more.
“I was like, count me in. So I joined the global virtual learning committee and, the first meeting I had with them the asked ‘New kid. Do you know anything about podcasts? I was like, yeah, totally.’ Because I did listen to, but I've never done one, but you know, it's the entrepreneur answer to everything.
It's like, yeah, totally. I can figure that out. And that was the beginning.”
Sometimes our actions in time’s smallest micro-moments lead to big adventures. Christine Fisher and I discussed this same thing on her podcast episode: Adventurous Career Investments. Next time your intuition tells you to leap in, DO IT!
Radical Candor
How would you respond if you were told you haven’t grown in 10 years? It would likely feel like a gut punch. Would you get defensive and deny? Would you be sad and cry? These would be logical responses. This happened to Dave.
A board member and friend told Dave he hadn’t grown in a decade. The board member didn’t say Dave was a bad leader. He just offered up a bit of radical candor from his personal vantage point. Dave could have rejected the observation. Instead, he used it as a leadership wake up call. Dave decided to ad critical “thinking time” to his daily routine to work on himself.
“About a year ago, I was in a board meeting. One of my board members said, ‘You know, Dave I've known you a long time and you haven't grown as a leader since the last company. So this is just me giving you a little heads up. Like I have not seen a lot of growth in you in the past 10 years or so.’
And I woke up. He said it gently.”
I haven’t read Radical Candor by Kim Scott. Dave received feedback that closely fit the bill. It was sincere, specific, and clear.
Are you prepared to receive radical candor? Do you have people in your network whom you can trust to provide it?
Carve Time to “Think”
Dave took specific action upon receiving feedback from his board member. He carved out time to “think” in his schedule. This might sound simple. It isn’t. There are always more immediate and known problems to address. The to-do list is never ending treadmill you think you can control. You can’t. It will control you if you let it.
Carving out time to think is requires discipline and personal empathy. It requires constant management like pruning a banzai plant. It requires focus driven by your ability to hear what is needed in your life. Here’s how Dave approached it…
“I have a time blocked off that says think. I took myself out of my office. I put my phone away and I had a pad. I'm like, now what? It took me a little while and what I realized that what works for me is I go to these sessions now and I don't do it every week, probably end up doing it twice a month, but it's still really valuable.
I go to these sessions with myself and I ask myself a question. The question is something that might be related to work or it might be related to something that I should be thinking about, like where is this industry going? In two or three years, what's going to be unique in this industry?
That's a question a leader, a visionary needs to be asking themselves and then have that conversation with other people…”
This approach applies to both job and career. Carve time out on your calendar. Find your thinking place. Ask yourself key questions and take notes. My thinking place is running. In 30 - 60 minutes I collect a half dozen thoughts to fuel my work as a writer, content marketer, growth leader, innovator, dad, and husband.
Doing Just Fine
How are you doing? Are you “fine?” Dave was doing just fine in his corporate career. His managers told him he lacked a sense of urgency. One even told him “you walk too slow and smile too much.” Never mind that this kind of managerial advice is terrible. Dave got fired because he was doing just fine. Then he did more than “fine.” He excelled.
“If I ever were to get a tattoo, that's what it would say. Walk slow, smile more. And it doesn't mean lazy. The walk slow. What that means is enjoy the journey. And I think that's where it broke down for me. I was chasing the money.
I was chasing the path that I thought I should be on. Yeah, I lacked a sense of urgency. I didn't really feel like doing anything that I was doing. It was interesting. It was fine. I completely lacked this drive and so that's why at 30 years old when I was fired from my job I found something that I could own for myself. I ended up building that and selling that for a shit ton of money and it was awesome.”
Dave’s journey isn’t for everyone. Building a company and selling it for a lot of money is REALLY TOUGH. But, his message is pertinent to all of us. If you are doing just fine and lack urgency, ask yourself, “What has to be true?” What has to be true to enjoy work? This might mean you need to incorporate your interests into your work more fully. It also might mean it’s time to move on to another gig.
Listen to the full story
Dave has lived both big corporate and entrepreneurship. His thoughts will help encourage people who are feeling a lack of urgency in their current gigs to identify how to be engaged. Plus, his story about interviewing adventurist Bear Grills is a fun listen.
Enjoy the episode! Thanks for you support!
Paul G. Fisher
I’d love to hear from you. Have any guest recommendations listeners should learn from? Shoot me a note!
Walk Slow, Smile More