Summer Roller Coaster: moving from NY->CA->NY
There’s so much to write about from this summer…but let’s start with the basics: I moved from NYC to Palo Alto and back in a span of a month and a half. Since a lot of people are surprised to see me back and I go through the story a lot in person…I’m going to talk about what happened with this summer rollercoaster. Interested in entrepreneurship? Get ready to hear ‘rollercoaster’ often.
This is a long post, but I hope reading this is worthwhile for you - some lessons learned include: trust your gut, references should all be A-OK, don’t let go of key team members for replacements until the replacement starts, time and communication are key indicators of commitment, always be recruiting, avoid intellectual boredom, a deal is not done until it’s done, and be prepared for the worst-case scenario. Lastly, when you aren’t prepared for the worst-case scenario and you are met with it, come up with a plan or four quick.
It started with a
post draft of a blog post that I wrote but never published called “Goodbye NYC.” It started a little something like this:
To say that the New York City entrepreneurial community has developed over the past few years would be an understatement — flourished, or transformed, would probably be more accurate. Foursquare, in vogue companies like GroupMe and Turntable, and the next white-hot companies (who happen to sit next to us) Art.sy and Neverware are all testament to this, with the latter two headquartered at the new epicenter of Silicon Alley — General Assembly.
Unfortunately, despite being born and raised in NYC (Stuyvesant HS holler), I’ll be moving to Palo Alto over the next few weeks to take YouAreTV to the next level. Two entrepreneurs who I consider good friends, blazed this trail over the past year and have enjoyed success thereafter. When I found out they were moving, I was bummed; as such, I appreciate my friends’ efforts to convince me to stay.
The premise of the post was primarily around my some of the struggles that we endured along the way with CollegeOnly and YouAreTV and the difficulty of finding a strong technical counterpart — but that will be left for another post.
With incredible delight and two years of searching, the draft of the post read
The reason I am moving, then, is…I have found a solid technical partner.
I had been searching and reaching out to the dozen or so top candidates in small world of the bi-directional video space. This individual, let’s call him Ted, in particular was a perfect fit — we connected on LinkedIn through a mutual friend. We spoke a few times on Skype and then I flew out to CA to spend the weekend with Ted in early June. During that time, he let me know he would start working with me in early July, I was super pumped. We begun parting ways with our developers, started to wind down most of our NYC operations, and I stopped recruiting for the CTO spot. Bad idea. Although I continued discussions with potential #2 or #3 hires or contract help, I shifted my focus to this new journey.
A few weeks later, during the reference/finalization process, Ted let me know that he wouldn’t be able to start until mid-August because of obligations at his current company, but would be able to start part-time at the agreed upon date. This was a major red flag to me, but my advisors let me know that it’s normal.
I had get togethers with both personal and professional contacts letting them know that I was moving out indefinitely. I made plans accordingly and, in early July, I flew out to Palo Alto to work with him.
It made me think about something one of his former CEOs said - the only single negative part of the reference checks. When I did word association (“Would you associate this word with this candidate”) for “dishonest,” there was hesitation. Apparently the separation process between Ted and that company did not go smoothly. I figured it was normal that things might be kind of awkward. As someone who values honesty above almost all, this should have been a complete red flag.
My mom had warned me not to move across the country for one person, but the caliber and fit of this individual made it seem worthwhile. One of my investors strongly recommended that I move out there, and almost all the other investors agreed.
At first, things were great. The weather there is perfect - 75 degrees, 0 humidity, sunny, EVERYDAY! I was living with my good friend from school Joe Perla so that was cool. I also had the amazing opportunity to meet and play hockey a few times with Guy Kawasaki (who is awesome) and Evgeni Nabokov (pro NHL goalie). I had a standing desk, as featured earlier - baller. I also started to get back into shape. I was hanging out with Bay Area Princetonians and meeting amazing folks in the entrepreneurial community. We also had a great third roommate, Austin, who was the chef of the house.
Fairly quickly though, things started to be not so awesome. As a city kid, I started to feel the isolation of living in Palo Alto and not working in a coworking space. Ted didn’t end up working nearly as much as he said he would before his actual start date, red flag. As we were discussing completely re-architecting the site from scratch, we were blocked on development progress (back and front-end) pending his work, decisions, and overall impact. Instead of working the one day a week and 2-3 nights, I saw him maybe once a week for about 2 hours, some weeks I didn’t see him at all.
Because of the technological difficulty involved, YouAreTV has taken a very long time to execute on and release (subject of another blog post) which goes against one of my key suggestions: get product in the hands of users as soon as possible. It’s so important for team morale, in addition to all the critical reasons according to the preachings of Eric Ries, Trevor Owens, and the Lean Startup Movement. Morale and momentum are critical for startups.
While waiting for Ted, there wasn’t much real work that I could do and my morale declined…my mind started to wander — should we productize our technology in a different way? What are our competitors doing? Are there other companies doing interesting things that I should be aware of? How are all these companies in TC, Mashable, VentureBeat raising so much money? It felt like the world was just passing me by — it was. I spent a bit of time learning more about Rails, but I should have really spent more time reading, learning, and keeping my mind active and/or meeting with people.
To make matters worse, in late July I pulled my hamstring and could barely walk for a week. It wasn’t until month and a half later that I ran a mile for the first time since pulling it. Anyway, I digress.
It was early August and almost time for my new co-founder and CTO to start. I was incredibly excited to start working with Ted and we (with help from you know who you are) finally got the API we’re working on top of and our app to work smoothly throughout the full course of one of our shows for the first time. I was starting to get connected to the Bay Area start-up network and spending time at Facebook/Google/etc meeting with cool people and attending interesting events.
The highs and lows continued. I realized we shouldn’t support a full production operation until our product was completely done, tested, etc. The night before Ted was supposed to start, he sent me an email saying he had to spend one last week at his company to finish things off because of the success of one of the products they launched. Friday, he said, we’d start for real. I was pretty freaked out, but “Friday it is” I texted him. Warning sign.
That Friday, I let Ted know that we need to trim down the team further and discussed some strategic plans. He only spent an hour and a half with me chatting about the opportunities we had for disruption from a product and content standpoint and that we should reach out to another individual to join the team as an additional technical co-founder — which would have given us an incredibly strong bi-directional video streaming team.
That night, I flew to NYC on the red-eye and the next day and parted professional ways with my best friend out of necessity for a variety of reasons - not easy/happy. Fortunately we are still BFF.
The night after, I was back on a plane to CA. Our flight was delayed so I didn’t get there until after Midnight —- so the Caltrain was closed. I took a cab (expensive) back. In the cab, I was exhausted, but I looked at my phone and saw that I had an email and/or text message. I literally thought, “I really hope I don’t get a message from Ted.”
Sure enough, after midnight on the day Ted and I were supposed to really start (after pushing back a month and then a week), I received an email from him titled “Involvement with youare.tv going forward:”
Hope you had a good trip back.
Would like to discuss with you about my involvement with youare.tv, and I am sorry for the change.
Things have changed in last 36 hours, since a few people I am leaving [company name redacted].
There are a few very exciting opportunities just surfaced, from idea stage to growth stage, andall are working on very disruptive products and technologies,
All these sounds exciting, and I would definitely like to explore further - still too early to tell,but sounds very exciting.
Would like to discuss how I can best help youare.tv going forward, maybe an advisor role to helpyou recruit a few engineers to work on the product.
We can meet early next week to discuss further.
Also, I will not be available Monday, but can meet together Tuesday afternoon.
I am very sorry about this change - really get attracted to the news things.
I closed my phone and fell asleep in the cab until I got back. I woke Joe up, I let him know what happened and that I was going to move back ASAP. It was not a happy night. Over the course of the next two days, I told all of my investors what happened and fortunately they were all very supportive, though I knew I lost a lot of confidence from some of them. One described what happened with him as “the single most unprofessional thing I have ever heard of.”
Obviously we had a signed employee agreement, but as you can tell, apparently that doesn’t matter much - legal docs are a prerequisite, but they only go so far in startups - early on, it’s about commitment, honesty, and trust.
I let Ted’s former CEOs [the one who hesitated on ‘dishonesty’ word association] know what happened, and apparently Ted did something similar to a very well-known and established company (something that didn’t come up in neither his references nor his LinkedIn profile [and obviously not in conversations with him]).
Two days later, I shipped my hockey pads back. That night, I met with my landlord / friend and his co-founder and let him know what happened and said my goodbyes. Two days later, I met up with my friend Zach and talked to him for an hour or so about how a small ripple can cause a tidal wave of success and individual events can have a tremendously negative impact. I let him know I was bouncing back to NYC, and that he could have my exercise ball [apparently he is sitting and bouncing on it right now as we gchat]. The next day, FedEx picked up my stuff. An hour after that, I was on the Caltrain to SFO to fly back to NYC permanently.
Although it was a huge blow, I’m still incredibly excited about the work that we are doing on YouAreTV now, though disappointed because of how much of an impact Ted would have had in taking us to the next level.
Fortunately, I’ve been able to put together a backup plan or four (as encouraged above) quickly. We still have Davis (intern turned super-coder) on the team and we are actively (and rapidly) improving the product, about to launch a redesign, start to see if we can sustain a large number of concurrent users (500+) on our platform and begin working with Merton, the person who inspired YouAre.TV.
The next month will be a critical time for us and I’m looking forward to the challenges and excitement ahead…back at home in New York City.
Above I listed a multitude of lessons that I learned from this ordeal. As one of my former chess coaches, Svetozar Jovanovic, always said “You learn a lot more from a loss than you do, if anything, from a win.” While it’s always better to win, the lesson learned here above all else is there is only one person you can really, truly trust in making critical decisions and executing thereupon - yourself. As noted, trust is critical - and if your gut indicates you you probably can’t or shouldn’t trust someone - either exhaustively figure out and deal with it, or, more likely, hit the big red stop button and shift gears.
Yes, in case you were wondering, we are looking for a CTO with significant experience in the bi-directional video space and management/recruiting experience.
Been holding off on sending this for a while until our new layout went up (last night), so nice coincidence that it is now time for a sweet new year. Shana Tovah.