An End To My Independent Life & Why I Now Work at RateGravity
Legit photo credit: Ally Schmalling. Deliberately hacky photoshopping: Yours truly.
For the last year and a half, I have accidentally stumbled into being an independent contractor. After leaving my last startup in a bit tumult, I was not actually looking for work. In fact, I was determined to not work at all. However, I now am starting another chapter as Chief Marketing Officer of RateGravity, a seed-stage startup that is out to revolutionize the mortgage industry.
I am thinking to myself, "How the hell did I get here? Another seed-stage startup? Are you really doing this again? What are you, nuts?" The announcement goes public today in a few hours, so I thought I'd try to take some time to reflect on the journey that got me here.
I: What Did You Learn, [Loser]? The month after I left my startup, my father-in-law and I went out to dinner. As the former Amtrak Chief of Police, he has a gift for cutting all the crap and getting to the heart of the matter. He asked, "In life, you either win or you learn. So, what did you learn?"
Ouch. OK, I didn't know what I learned. I was burnt out. Cashed. In fact, I was looking forward to my time "on the beach." More gooey blender drinks. Less thinking.
Ironically, I never afforded myself that luxury. I think I was just too scared to answer the questions directly. A former investor quickly brought a due diligence project. Another friend asked for another project help. Snowvation needed sales, marketing, and temporary executive leadership, and I was determined to ensure that ShredBetter would not have been sold in vain (BTW, Snowvation is kicking ass).
Looking back, I think I used work to defer having to answer the hard questions. This cycle repeated itself in random ways about 6 times in the last 18 months. I consider myself very lucky and thankful to my friends for being so gracious and open to letting me into their enterprises. What's more, that luck bought me enough time to assuage my own fears, I think.
II: For Hire: CXO With Commitment Issues So I worked, and through work often comes great therapy. As the great activist once Grace Lee Boggs said, "You make your path by walking." And in that walking, I think I have figured some things out and have a clearer answer to my father-in-law's question.
By seeing lots of growth and turnaround companies, I have gained newfound perspective about what I learned from my last startup: I honestly failed to continually evaluate my own 3 Questions This Over-The-Hill Entrepreneur Asks (if you don’t at least scan this link, the rest of this piece may not make sense to you, if at all!).
FFS, I wrote this myself about myself. Idiot. While I wrote this just before my 40th birthday, it has all the awkwardness of a high school prom photo. But you just have to embrace the awkward.
Fail 1. My co-founder and I jumped in too fast, never knew each other as people. It was a startup version of a shotgun marriage. Thus, I failed to answer my own Kidney Test: Would I give my business partner my kidney? I really never took time to answer that question with an open heart and wide eyes.
Fail 2. I also failed my Uzo Abada Test: Where will my art live? We didn't define roles or what we individually owned. Through poorly constructed founding relationships, there was no place for my art to live. Despite guidance from my lawyer and friends who shared their co-founding disasters, we just forged ahead and said, "No need for explicit roles. We'll just figure it out later."
All bad moves. But I did it anyway. Fail. Fail. Fail.
So Horsepowered Partners was reborn. Originally only intended to be a shingle for my side project ShredBetter, Horsepowered evolved into a very comfortable consulting model. I was able to de-risk myself personally and professionally. I figured I sucked at answering those 3 big questions for a founder, so why try?
Most of my projects were tidy 60-90 day projects. Everything was by referral. I took a little cash from my clients, usually a little equity, and sometimes hired my long-term successor. I didn't want to be around forever. See it, fix it, exit. I toyed with renaming Horspowered Partners to Your Rebound CXO.
Subconsciously, I think I was hoping to just finish that last project for my beach time, which never came. To illustrate, I did a lot of digital marketing, yet have no website myself. Serious commitment problems, for sure.
III: Gravitational Pull And now, I begin another chapter at RateGravity. It started as another one of my projects, "Hey, the person we were hiring fell through. Can you hold us over? ... Sure, no problem." 30-day contract. Then another 30. And now here we are full-time.
So, did I learn anything? I think so. Let's run the 3 Tests again.
1. Kidney Test: Would I give my partners my kidney?
You may not believe this but the founder, Patrick Boyaggi grew up in the same freaking Cleveland suburb that I did, Westlake. Unreal.
In the two months we have worked together, we have also both worked hard to get to know each other as people. I've stayed in Patrick's house, played with his kids, and gotten to know and adore his wife. We've tried to connect as men, fathers, husbands and also desperate Cleveland sports fans. Our kids have said hi on Slack calls. Is it kidney-worthy? No, but it's darn good for 60 days.
That has extended to the rest of the executive team, where I spent extensive 1-1 time with each of them. While it's not perfect, it might be the most I know about my co-workers before I started a job except for starting ShredBetter with my lifelong friend Brian Morgan.
So does this pass the Kidney Test explicitly? Probably not. But that's a really high bar, and probably bears revisiting. The point is, in being wiser this go-around, and spending 60 days working and acting like a member of the team, I know more than I've ever before in approaching a new job.
2. The Kid Test: Can I explain this to a 7-year-old?
Me: You know how we had to borrow money to buy our house?
Jack (now 8): Yeah.
Me: Well, Daddy's new company helps save people lots of money on that loan. We shop all the little banks for them and they can get deals that the big banks won't give them.
Jack: Like when you used to work at Bank of America? And how much money?
Me: Yup. Average? About $29,000. It's like getting our minivan for free.
Jack: Cool. Can I get a computer now?
Check.
The mortgage industry is quite a stacked deck. If you know me, you know I am a sucker for companies that overturn large entrenched business that accumulate wealth on the backs of everyday people. I've been involved in this idea in many industries from financial services to funerals to fashion. If there is a way to disrupt inequitable structures and give Jane and John Public a fair shake ... well, you have my interest.
That's the core of RateGravity's business model and founding story. Patrick was an exec in a major lending company. But when wanted a loan himself, he hacked the mortgage supply chain. He went direct and got a rate that no one else could get. He thought, "Wait. That's the business. Why should I be the only one to get this? We make money on people not 'seeing our screen."
RateGravity is about flipping the screen, hacking it, and saving people money. I'm in.
Oh, and by the way, you are overpaying for your mortgage. For now.
3. The Uzo Abada Test: Where will your art live? That's one of the beauties of working together for 60 days vs. interviewing for 3 days. As my good friend Farhan Thawar correctly writes cites, interviewing is garbage. My art is already living. And I think there is more to come.
With RateGravity, we've already had more than a couple of "passionate differences of opinion." What's more, we have worked it out. Even before we agreed to full-time terms, the team allowed me to implement and change several keystone parts of the business such as brand, CRM, analytics, and content. The impact of these decisions extends far beyond my consulting tenure. There is a mutual respect for each other's roles that has already been tested. I am confident stuff will get out in the world ... and that's all I ever wanted.
***
As I look back among all this, I still at times doubt my own heuristic evaluation. However, my wife, Katherine, is an amazing partner -- my best friend, and my best advisor. While in compensation negotiations, always the most fun part of any recruitment, she said to me, "Look, I haven't seen you engaged in your work like this for over 2 years. It's nice to see you like this. If you can get it done, then just do it."
Well said. And I did.
OK, enough navel-gazing.
Fired up. Ready to go.
