So much trouble on my mind

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.

Our bank account took forever to get and there is no good reason why. This is not going to be a super deep post but rather more of a public service announcement / instruction manual in hopes that some other entrepreneur or business owner won’t have to go through the same logistical hell that I went through. There’s a lot of confusion out there as to what you have to do to get a bank account as a foreign limited liability company in New York

Here is all you need:

Operating Agreement of your LLC

IRS Letter granting your Employer Identification Number (EIN)

Banking Resolution saying you need a bank account and specifying who can sign

Certificate of Good Standing from the State of DE

I was able to get 1-3 from when I incorporated (I used Incfile.com and it was like $300 all in), but we drafted a more comprehensive Operating Agreement later with our lawyer (thousands more, but that was another post).

I got 4 from an expedited service ($99 - just google it) since I was in a time crunch but you can get it straight from DE for $50 if you can wait.

That’s all you need. You should be able to go to a bank branch, ask to speak to a banker (not a teller) and then it should be about 30-45 minutes to open the account.

Here are things I wasted time on.  Don’t be a fool and fall prey to what I wasted weeks on:

LLC Publication Requirement -- There is an old, arcane law where LLCs have to pay for an announcement in a newspaper stating our LLC was it is open for business.  And then, you are supposed to get an official form from New York State saying you have fulfilled this requirement.  I was told I had to have all those ads and accompanying certifications done before I opened an account. While you have to do it (technically-speaking) to do business in New York, it IS NOT part of what I eventually had to turn in.

Small-town / Inexperienced Bankers -- I was told all this above by my local suburban branch.  I actually called Incfile to see if this was true (which my lawyer said was - technically) and the rep recommended I just keep trying different branches.  He had never heard of this before.  So I did it in Manhattan, where there is likely more business volume and I was out the door in 40 minutes. 

“ What do you want out of Incubator X?*” asked the interviewer.

I replied, “Community.  Being an entrepreneur is the loneliest place in the world.  It’s like moving to New York for the first time.  You are surrounded by 8 million vibrant, active people but you are often alone wondering what’s wrong with me. Why am I stuck home alone with a can full of Pringles and reruns of The Iron Chef?” 

“I think New York is now the 2nd loneliest place on Earth. Starting your own company is now #1. I want to be around people who are going through what I am going through.”

And that is the honest truth.  There’s this “Everything is Awesome” mentality that pervades coffee shops, bars, and the press.  You hear it all the time. Oh, my brother just started his gig, crushing it ... My friend is at Exit Company A .... My former colleague started XYZ and is killing it. 

It’s bullshit. 

If you are an entrepreneur, run from these people.  Or at least change the conversation to small talk and grab yourself a drink.

The people I choose to combat this with are people who have a genuine search.  They know every day is hard and the direction is unknown. Those are the real creators. People who tirelessly grind with a mission. 

This presentation by my Orbital colleague Tina who hits the nail on the head (and has amazing projects about food).  To me, it’s a must read.  She gets it. Creators are generally long on problems and searches, and always short on progress or solutions and honest about that. 

But that is the struggle.  And that is why anyone who is *really* doing it, would never say “Oh, I am crushing it.  Killing it.” They know its bullshit. Even those who I know who have the next unicorn on their hands think that the road is so long and there is so much to do.  Mostly, they feel lost in the vastness of their quest.

That’s not to say that there haven’t big successes in Coeio’s path so far (there have), or my partner and I aren’t working together in lockstep (we totally are), or there aren’t days when feel we like we can beat the world (we do); but the progress made vs. the open questions is forever a completely daunting, unfavorable equation.

Lastly, these are not a niche virtues. I think there is a piece of everyone who aspires to this.  I recently rediscovered David Brooks’ piece on The Moral Bucket List, (another must read) where he extols the virtues of building “inner character” vs. “external careers.” He writes that these people don’t feel like captains of industry, but really stumblers:

The stumblers occasionally experience moments of joy. There’s joy in freely chosen obedience to organizations, ideas and people. There’s joy in mutual stumbling. There’s an aesthetic joy we feel when we see morally good action, when we run across someone who is quiet and humble and good, when we see that however old we are, there’s lots to do ahead.

At risk of being lonely, that’s the company I choose to keep these days. 

And I am more than OK with that. Here’s to lonely stumbling!

(Photo credit: Steven Miyao)

Nearing 40, I’ve been in big companies and other founders’ startups, but never have really taken a startup from the ground up. I used to think it’s a domain reserved in mostly for the twenty-something hoodie set (some think 35 is washed up).  

I do feel old, and at times out of place. I know I am not the only one to feel that way, as I am guessing whoever asked this on Quora had the same feelings of awkwardness (no, it wasn’t me).

That said, I believe my age has taught me powerful life lessons that I hope to take into Coeio and beyond.  As I’ve talked to many people my age who are considering their next role, I share with them the three questions I asked when I decided to take the plunge.

1. The Kidney Test: Would I give my business partner my kidney? 

Yes, my kidney. 

When I was younger, I used to ask myself, “Would I go to war with this person?” These days, I want I want more.  It’s not enough that my partner have amazing, world-class complimentary skills to me (I am so lucky JR does), but that they also have to push me to be a better person, personally and professionally. 

Being awesome at your job is a necessary, but not sufficient, condition to start a company with you.

I spend more time with my business than with my family, and so I want to feel that that is time of my life well spent.  We all have gut feelings about people, and the Kidney Test is a good checkpoint to see how strong those are.  

2. The Kid Test: Can I explain what I do to my 7 year old? 

This isn’t just a marketing pitch test, it’s a purpose test.  I want so badly for my kids to do something meaningful and important with their lives, that I have to live it.  Here is a real conversation I had with my daughter last month:

Elizabeth: So what’s your new company do?

Me: You remember when Gong Gong and Po Po (grandpa/grandma) died?

E: Yes.

M: We are making stuff that let’s the bodies go back into the ground naturally rather than be in the coffins.

E: Like our compost pile outside that helps the environment?

M: Yes.

E: Cool.  Can I help?

I will never forget that conversation, it was the first time that I have been able to really connect my work with something my kids not only understood, but wanted to pitch in.  It’s changed my motivation to work immensely, and I hope I never have to give that up.

3. The Uzo Abada Test: Where will your art live? 

The actress Uzo Abada who plays ‘Crazy Eyes’ Suzanne on Orange is the New Black said gave an interview on NPR that I will never forget.  On why the show saved her acting career, she says:

It gave me an opportunity and a voice to speak and let my art live, which is all I've ever wanted to do.

That interview hit me between the eyes like a hammer.   

Unlike much of the corporate world where output is private or subjective, art is not. Art can’t hide. It is there to be seen, judged, lauded, criticized, revered, and even feared. Art has the creator’s heart and soul on a canvas, episode, plate, album, etc. There it sits.

After spending a fair amount of time in the corporate world, I see what a hard and rare gift the ability to make art is.  So much corporate work is subjectively judged by a small group: your boss, a select small group of execs, or clients.  

Again, since I am nearing 40, I want to be the 8-year old at the Lego table again and make something for everyone to see. 

Hi-five me or say it sucks. I am cool with either. 

For me, Coeio and the suit was that.

And it’s just about escaping corporate life, the rule needs to be applied to startups as well.  To illustrate, I considered a lot of starting up some things in adtech with some very awesome, successful people.  All are continuing without me in their own endeavors and I hope they all become incredibly successful. That said, I passed at this stage of my life.  Right now, adtech fails the Uzo Abada test.  Few would see the art of advanced advertising analytics or optimization algorithms, no matter how elegant or efficient.

Happiness: The endgame

At risk of getting overly personal, I’ve been much more lovey-dovey at home.  I asked Katherine my wife, why and her response was brief:

Because you are happy. 

She’s right. I realize that these are high bars, and I don’t know if I will always be able to apply all three at once, but I know they are out there.  Even if I have to make a return to corporate life (I am not adverse to that), I hope that these are the questions that I will continue to answer.  

In New York, like most places, the second question someone asks you after your name is either where you live, or what you do for a living. 

When I say “I run a funeral startup,” I’ve been amazed by the responses.  I’ve started asking people if I can photograph them if I tell them to get their first reaction. 

If a picture says 1,000 words, I will stop this post now and leave you with 3 of the archetypical responses so far -- but it all makes me think we are onto something.  You will see more here on the hashtag #coeiowhat

(FYI, these were taken at the Asian-American Tech Entreprenuers Summer BBQ - explains the whole Asian thing.)

The “Really?”

The “Holy Sh!@$@#@”

In the name of starting a new page, I wanted to let everyone know that I have started a new endeavor, Coeio.  Site is super ugly right now, but that’s how it goes. 

It is a startup that is going to be focused on delivering green funeral products, along with my partner, Jae Rhim (”JR”) Lee, who is a TED fellow and gave a super famous talk.  She is awesome I am lucky to have met her. 

The funeral industry is a $20B+ market in the US that is ripe for innovation; however, the reasons for taking this on are more personal than professional.  Many think I am crazy to have quit a senior executive job at Bank of America, but I lost my grandparents last year. For those who are friends with me on Facebook may remember what a profound impact that it had on me.  Meeting JR this year at Stanford made all these events feel like a calling that had to be answered at this time in my life.  

Through working on Coeio, I hope that I can find a way to figure out a way to make that terrible process better.  

One way to get a glimpse of what we are doing is to check out our first project on kickstarter (not live yet - but will be soon, would love your feedback).  We are telling the story of our first customer -- an amazing man I’ve met named Dennis White.