I want to share with you the story behind why I started ShareWillow, a platform for small businesses to design and manage incentive plans.
I’m dedicating the next 20 years of my life to this mission and here’s why…
In 2012 I was working at a big corporation.
I was grateful to have a job but I found myself scrolling TechCrunch and more attracted to startups than corporate life.
I didn’t know it at the time but I was desperately seeking to create something.
In the summer of 2012, I was fortunate to meet a young, passionate founder of a small business in Reston, Virginia named Vincent.
Vincent was exuding passion and excitement and just talking to him about his company left me inspired and energized. I wanted to join him.
His business was really small, doing maybe $10k per month in revenue, and didn’t have the budget to bring me on full-time with a salary.
I pitched him an incentive plan that would reward me with a rev share from new customers that I closed and some equity that would vest over time.
Luckily, after some back and forth, we agreed to an incentive plan and landed on a deal.
I immediately quit my corporate job.
I noticed my motivation and behavior instantly changed once this happened.
To reduce my personal expenses, I rented out my bedroom and slept in my living room. I cut my burn down so that I was only spending money on things that I absolutely needed to survive. Read the full blog post on that story here (it’s actually a crazy story).
My first few “paychecks” (from new sales I brought in) were small but I could see how it would grow over time if I dedicated all my energy to the company.

Some of my early paychecks at mHelpDesk
Since my personal incentives were aligned with the success of the business, I spent every waking hour thinking about how I could make the business successful.
I adopted this mindset and motivation without being a founder of the company - I was simply an employee with an incentive plan.
Over the next 1.5 years, we were heads down growing mHelpDesk.
Quick scroll through time on some photos to see the growth…

January 2013 (Vincent’s house lol)

March 2013 (free office space at AOL)

September 2013 (working from Bahamas)

November 2013

February 2014

May 2014

August 2014 (Me and Vincent were on the phone negotiating the sale of mHelpDesk)

June 2015
Eventually in August 2014 we were acquired by HomeAdvisor. This changed my life.

Visiting HomeAdvisor after acquisition
I went from sleeping in my living room and making no salary to having a bank balance with at least one comma (maybe more!).
But it didn’t stop there.
I was able to parlay that win and confidence/motivation to starting my own small business called PhoneWagon in 2016.
After 4 years, PhoneWagon was acquired by CallRail. And my bank account grew even further.
How does someone from a lower-middle-class background (emphasis on the lower) with $50k in student loan debt go from unmotivated and working in a cube for $62k/year to having life changing money in just a few years?
Was I just getting lucky? Or was this driven by something bigger?
Was there a deep change in motivation that began in 2012 that led to these extraordinary outcomes?
I was seeking answers and was determined to find out why this happened to me.
Both of these companies (mHelpDesk and PhoneWagon) sold software to small businesses (think HVAC, plumbers, marketing agencies, etc). A common theme I would hear from customers over the years was how difficult it was to find and keep motivated employees.
During these conversations I kept thinking back to my own motivation. I wondered why these businesses weren’t able to unlock that deep motivation from within their employees. The same motivation that unlocked from within me and changed the trajectory of my life in 2012.
I knew that if the motivation was within me, it had to be within their employees too. I just didn’t know of a solution to help them unlock this motivation from within their employees.
Then something happened in 2023 that gave me all the answers.
In May 2023 I flew to a family friend’s wedding in Italy. I wasn’t supposed to go to the wedding but due to someone else dropping out, I received a last minute invite.
At the wedding I was randomly seated at a table next to a nice couple named Chuck and Stacy. Chuck owns a moving company outside of Washington DC called JK Moving & Storage. He mentioned that he started the company 25 years ago from his garage and now they are the largest independent moving company in the United States.

idk why they’re touching my hair but this is me and Chuck at wedding in Italy
I was fascinated and curious about how you grow a small local moving company to be the largest independent moving company in the country (according to Google they do around $300m in revenue).
I started asking Chuck a million questions about his business. One thing that stood out to me was that he offers profit sharing to all employees.
Chuck mentioned how profit sharing aligns incentives and motivates their employees to act like owners. He said profit sharing enables all employees to participate in the upside of the business when they have a good year.
He said he celebrates the wins with his employees too. He posts on LinkedIn every year with a photo of him and his employees and a big check with the profit share distribution.

Employees love it and it shows potential future employees how JK Moving & Storage is a company that shares profits with employees… a huge benefit over other moving companies.
I was inspired.
Chuck’s story about profit sharing reminded me of a blog post that I read a few years prior.
Nathan Barry of ConvertKit wrote a blog post about how ConvertKit does profit sharing.
I actually made a comment on this blog post in 2020 (which is still live today) that I was going to build a SaaS tool for profitable companies to build and manage profit sharing plans.
Jason Fried from Basecamp writes about how they share profits with their employees and how it’s been a huge unlock for the team. He tweeted here how they shared 6-figures in profits to 20 employees for 2024.
Okay wow. Lots to unpack.
There’s a pattern here.
We have my personal story about how incentives changed my life, Chuck’s story about how incentives helped him build JK Moving & Storage to the largest independent moving company in the country, and Jason Fried using incentives to grow Basecamp into a $300m+ profitable company.
The obvious pattern here is that employee incentives are helping these companies achieve massive success.
After this realization I felt incredibly inspired and decided to start ShareWillow.
When I sat down to think about the “why” behind ShareWillow, I wanted to answer the following questions:
Can we impact the outcome of small businesses by helping them design and manage incentive plans?
Can we help small businesses create incentive plans that motivate employees to act like owners just like I was motivated from an incentive plan back in 2012?
Can we help the next small business become the largest independent business in the country (in their industry), just like JK Moving & Storage was able to do?
Can incentive plans help small businesses achieve extraordinary results just like JK Moving & Storage and Basecamp?
I plan to spend the next 20 years of my life trying to answer “yes” to these questions.
And this is me creating my life’s work with ShareWillow and finally getting around to building the software that I said I was going to build in the comments of Nathan Barry’s blog post back in 2020.
It’s time to inspire millions of small businesses to motivate their employees and achieve extraordinary results.
Welcome to ShareWillow 🎉
PS - I’d love to show you how we can help you unlock deep motivation from within your employees.