How One Entrepreneur’s Persistence and Patience Led to Success

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In a recent Authority Magazine Q&A article, Fractional Leadership Founder and CEO Ben Wolf shares his story about the challenges he encountered on his way to forming his own business and why he never gave up.

Q: Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

A: I left the company where I “grew up” entrepreneurially — a healthcare startup called FreedomCare — because I realized that I like making massive change and building things and my ability to do that had plateaued. I accepted a role as COO at a smaller organization I hoped would be an even greater opportunity long-term to make a massive difference in their mission, growth, and organizational health.

While I knew about some of their major organizational challenges, I had already joined the company when I Iearned about some organizational dysfunction among the partners. This dynamic doomed me to presiding over a slow-motion train wreck I was powerless to avoid.  

I had just left a stable position and had to choose between the misery of feeling responsible to solve problems I was not permitted to even address and risking going out on my own with a wife and four children to support with no certain prospects. With my wife’s support and some savings, I had built up doing some consulting work on the side, I decided that the misery of staying where I was outweighed the risk of taking the entrepreneurial leap.  

I submitted my resignation two months after starting the new role and hung up my shingle as a Fractional Integrator, a term coined by Fractional COOs who work with companies running on the Entrepreneurial Operating System® (EOS®). I was very scared.

I began doing business development by having calls with business owners, various kinds of trusted advisors, other Fractional Leaders, and EOS Implementers®. I started a podcast called Win / Win — An Entrepreneurial Community, met with 12-18 people every week, and created measurables for myself to ensure I was doing the right kind of business development work for my new solopreneur business.

It was maddening at the beginning. Together with my beloved wife, before I was able to get any clients, it felt like that song from The Greatest Showman, “Never sure, never know how far we could fall. But it’s all an adventure. That comes with a breathtaking view. Walking a tightrope with you.”

Finally, after over three months, I got my first client. That was amazing! I helped drive massive change with that company and they grew their top-line revenue 25% the first quarter I worked with them. Things got a lot easier for me personally then, but we were still financially walking on a tightrope.

I continued hacking away at emailing, Zooming, calling, and meeting with people for another six months, always putting on a confident, non-desperate affect, when COVID-19 hit. All the business owners I was speaking with froze up, but I kept plugging away at the emails, calls, and Zoom meetings. I wondered whether I would ever feel successful. Would it ever get easier?

Then, in May 2020, the dam finally broke. As people’s paralysis broke and they realized they could no longer put their lives and businesses on hold, more and more started reaching out to me to be their Fractional Integrator. I got one client, and then another, and then another. Once I became fully booked, I began referring the leads I continued to get to other Fractional Integrators and getting invited as a speaker at various entrepreneurial groups. I began paying off my credit card and student loan debt. It was a huge relief I would never have experienced if I hadn’t kept up my weekly regimen of emails, calls, and meetings without regard to the self-doubt I felt.

Q: So, how are things going today? How did your grit and resilience lead to your eventual success? 

A: As John Astin used to say on Night Court, “I’m feeling much better now.” Because I kept going out there and helping whoever I could and connecting with more and more people, I started to develop a bit of a reputation as one of the most competent Fractional Integrators and one of the industry leaders in the Fractional Leadership community in general.

Because I continued getting so many referrals and leads for Fractional Integrator clients, I converted my “solo-preneurship” into a firm, Wolf’s Edge Consulting, with several other Fractional Integrators. I developed a proven process we took our clients through, identified what made us unique, and set up a meeting pulse through which we helped resolve each other’s challenges with clients. Now none of us are on an island, a challenge every solopreneur knows too well. 

And the people I met through my podcast, in the EOS community, and in the Fractional Leadership communities ended up making me realize that the whole Fractional Leadership world was completely fractured. There were thousands of websites by the various Fractional Leaders, both firms and solo practitioners, but there was absolutely no center of gravity in this relatively new industry. That ended up being my inspiration to write Fractional Leadership: Landing Executive Talent You Thought Was Out of Reach and creating FractionalLeadership.io as the first vetted Fractional Leader referral platform for business owners.

Read the full Authority Magazine piece, Ben Wolf of Fractional Leadership: 5 Things I Wish Someone Told Me Before I Began Leading My Company.”

Ben Wolf Author
Ben Wolf, founder and CEO of Fractional Leadership, has been on both sides of the Fractional Leader search process.
As a leader in companies where he served as Fractional Integrator (outsourced COO), he has searched for and found multiple Fractional Leaders for clients. And as a Fractional Integrator, he has gone through many cycles looking for new clients at the successful conclusion of each engagement.
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