Everything starts somewhere ...
Hello! š
Iāve been writing newsletters for Bullpen for more than a year, but this one feels a bit different.
This is the first installment of a weekly newsletter that will document the journey of building Bullpen to a $100M revenue business (more on where weāre at today below).
Why? Entrepreneurship is a big life endeavor, full of ups, downs, and valuable learning lessons. Itās worth documenting, and maybe one day my kids can use this to circumvent some of the mistakes that Iāve made.
Buckle up - itās going to be a ride.
A bit about me ā¦
My name is Tyler Kastelberg. I was raised in Richmond, VA, went to public school, and graduated from Virginia Tech with an engineering degree.
While that may sound pretty ordinary on the surface, what I didnāt mention is that I had a severe stutter when I was young (and a little that lingers today).
On the outside it sucked. However, it turned out to be my superpower - building massive resilience that equipped me to navigate the ups and downs of building a company.
Corporate wasnāt a good fit.
Before becoming an entrepreneur, I worked two corporate jobs - a finance role at GE, and an investment banking role at Raymond James.
I worked with some great folks, many of whom I still consider friends today. Ultimately, the corporate world didnāt suit me.
Iām not detail-oriented (important for both corporate finance and investment banking roles), and my desire for true ownership of my efforts made it tough to be a ācog in a machine.ā
I once read (or heard - not sure tbh) that you should only become an entrepreneur if you canāt imagine doing anything else ā¦ thatās definitely true for me.
My first business.
Iāve been working on Bullpen for about 4 years, but thatās not where I started.
After leaving investment banking, I planned to syndicate multifamily real estate in Virginia with a business called Kastelberg Real Estate. My plan was to raise money from investors in San Francisco (where I lived) and invest in the city where I was raised, Richmond, VA.
I thought it was a unique idea at the time, but it turns out that everyone was doing it. The competition was fierce, and I only ended up buying one property - an 8-unit multifamily building in Portsmouth, VA.
Long story short - it was a big mistake. I came out of pocket to make my investors whole and lost a bunch of money.
While pursuing real estate deals, I started to take on some freelance work for other investors in town. They needed help building financial models, and my banking background made people think that I knew what I was doing ( ā¦ I learned everything I knew from free videos on adventuresincre.com).
It turns out there were a lot of people who needed help with financial models, and I was able to grow my little consulting business by hiring a few freelancers from Upwork who would do the work while I managed clients.
Nearly two years in, I realized that I was the bottleneck ā¦
Enter Bullpen.
Nathan Latka (a fellow Hokie entrepreneur and SaaS expert) says that some of the best startup ideas come from consulting businesses.
Nathan recommends building a consulting business to $1M in revenue before pivoting it to a software business - my little financial modeling businesses made it to a few hundred thousand in revenue before I decided that the commercial real estate industry needed Bullpen - an Upwork of real estate.
You might be thinking ā¦ ābut Bullpen isnāt like Upworkā ā¦ youāre right, but in the early days, I set out to build a software-based, commercial real estate freelance network like Upwork.
I learned the basics of coding and created an Upwork replica on Bubble. I launched the software and watched as customers trickled to our site (mostly my old consulting clients).
There were several problems.
First, I had no idea what I was doing.
Fortunately, Y-Combinatorās Startup School content on YouTube taught me about product market fit, the lifetime value of a customer, and customer acquisition costs.
You might be seeing a theme ā¦ Iām a big proponent of learning by doing (financial modeling via adventuresincre.com, building software via startup school, etc).
One of Bullpenās corporate values is having a bias towards action. You can learn a lot through google and calculated experiments.
One of the biggest mistakes that I made was tricking myself into thinking that we had product-market fit and needed to raise money.
Armed with a slide deck and mustard seed of confidence, I set up calls with angel investors to raise a $1M seed investment. We ended up receiving checks from three different angel investors, for a total of $45,000 ā¦ a far cry from my $1M seed goal.
With the luxury of hindsight, I can confidently say that the failed fundraise was the luckiest thing that ever happened to Bullpen.
Rather than dump hundreds of thousands into a bad idea, I had to figure out how to build Bullpen profitably - it was time to bootstrap.
We pivoted.
Remember when I thought we had product market fit? I was wrong.
Our customers didnāt like using our āUpwork-likeā software. Our unit economics were terrible, and we couldnāt seem to make more than $10,000 per month in revenue.
However, there was one bright spot. The customers who called me to handpick a freelancer for their job typically had a very good experience and returned to hire more people (albeit through me, not the software).
Based on this, I knew there was a demand for fractional hiring in commercial real estate, but it wasnāt going to be fulfilled by my software.
As such, I laid off my 6-month-old team of Ukrainian engineering contractors and pivoted Bullpen to a sales-enabled, curated freelance network.
Side note ā¦ Remember that stutter? Cold calling and sales are not natural skill sets. Fortunately, Iāve worked with two very talented sales professionals that have helped us grow exponentially.
As a leader, Iāve had success playing to my strengths and hiring experts around me who supplement my weaknesses.
It worked!
After pivoting Bullpen into its current form, the business exploded.
My newly hired salesperson was slammed with work, and our monthly revenue started to grow ā¦ $10k, $13k, $18k, $30k, $60k, ā¦ $100k, $200k, ā¦
We hired a talent manager to help source and vet our freelancers, established more robust processes, and worked with a mentor who helped us hone our revenue model.
It was clear that we had achieved product market fit.
That brings us to today.
Bullpen became a 4-year overnight success. We currently average between $250k and $300k in monthly revenue (~$3M annualized) with solid sales, marketing, and operations team members.
However, itās not all sunshine and rainbows.
Iāll share more in future posts about the road bumps along the way, lessons learned, and what weāre doing about the current plateau that weāve found ourselves in.
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