Finishing Fights

Sports idioms are everywhere, startup world included. We talk about home runs ideas, ball park estimates, and (nonsensically) below par quarters.

These analagoies permeate casual conversation, board meetings, and all-hands, but they are (pun intended) off-base.

Building a start up isn’t a ball game, it’s a fight sport. What’s the difference?

1) There’s more than one way to win

In football, baseball, soccer, basketball, etc, there is exactly one way to win. You score more points than your opponent. When my (un)loveable loser Jets are down 20 points, their only hope of winning is to score 21. Hell, even quidditch, the sport from Harry Potter — a fantasy book full of mythical creatures, flying brooms, and literal magic —  follows this. The Golden Snitch just gives the catching team 150 points. If 150 points isn’t enough to close the deficit? Tough luck, your team loses.

Deficits exist in start ups and fight sports as well, and should not be ignored. Periods of poor, lagging performance can leave founders, boxers, and wrestlers behind their competition. If not corrected, time can run out, those deficits can become final, and the competition can be decided on points, just like all the sports mentioned above. However, unlike those aforementioned sports, those deficits can be short circuited.

No matter the score, no matter the time remaining, fighters and founders are never more than one punch, pinning combination, or well executed idea from breaking through and short circuiting, not closing, the deficit. It doesn’t matter how bad things have been, and how far behind you are. Until the final bell is rung, or the company is closed, there’s a fighting chance.

2) There are no substitutions

When football games become routs, both sides, winning and losing, pull their main players and ease up. The stars sit on the bench, the clock runs down, and the coaches prepare to shake hands. When a basketball player gets injured, he comes out, a sub goes in, and the game continues. In start ups and fight sports, this concept doesn’t exist. If a fighter gets injured and can’t continue, the fight is over. If the founders burn out and quit, it’s (effectively) a death sentence for the company.

Just like a UFC fighter needs to fight smart and not gas out too early, founders need to be smart about their physical and mental energy as well. To repeat a cliche I used to vehemently not believe, it’s a marathon, not a sprint. Finish the fight.

Agree or disagree? Let me know via twitter or email or elsewhere.

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Predictions for 2020

Since I love being wrong, here are my predictions for 2020

Bitcoin continues to flounder

Over a decade since creation, Bitcoin has failed to establish itself as anything else besides an instrument of speculation. Much like the year of Linux on desktop, the Bitcoin as currency movement isn’t happening, and the HODLers, most scarily, appear to have accepted that. Without the idea of Bitcoin as currency,  the price of Bitcoin will continue to be volatile, but overall deflate, as HODLers move on to newer and shinier altcoins. Markets can stay irrational longer than the participants can stay solvent, and if the participants are irrational as well, that can’t end well. I’m bullish about the blockchain as a technology, but Bitcoin will end up as the Sega Dreamcast of crypto.

Prediction: Bitcoin slowly declines, spending the back-half of the year under $5,000

Trump impeachment trial goes along party lines, Trump remains president

As the country gets more and more tired of impeachment discussion, Pelosi will have to deliver impeachment articles prior to the main stretch of the general election. McConnell and the Senate Republicans will run a show trial that introduces no new info, and will call none of the relevant witnesses. The vote will go along party lines, and Trump will remain as president (and tweet about being vindicated shortly after)

Prediction: Trump remains president, partisan polarization continues to increase.

Shitty companies will continue to stink, as market regains sense of smell

You can go up on a steep hill and look West, and with the right kind of eyes you can almost see the high-water mark—that place where the wave of insane Softbank fueled valuations finally broke and rolled back. The collective group delusion is done, and 2020 will be the real year of reckoning, for WeWork, Uber, Lyft, Peleton, and other money burners. With no one else to pass the bag too, we’ll see these companies scale back from their grand ambitions and turn into more traditional, smaller, less AI gobbledy-gook versions of themselves. On the other hand, at-scale companies with strong unit economcs (e.g the Zooms of the world), will continue to see their stock price rise.

Prediction: WeWork continues to shed everything besides office space in already established cities, Zoom gets back up to $90/share, Uber ends under $20/share, Lyft ends under $35/share.

Snap continues to show up it’s haters.

It’s been a banner year for the Snap (and it’s stock price), and there’s no reason why it should stop. The worst has happened, Facebook did it’s best to copy all of Snap’s offerings, and Snap stays bloody but unbowed. What’s left is a company with a sticky userbase that has realized it’s not going to be bigger than Facebook, and has set out to build a really solid (dare I say profitable) company, that is finding it’s own (very large) niche.

Prediction: Snap ends the year at over $22/share.

Highly Contested Dem Primary leads to Biden nomination, Trump victory

An overly crowded Democratic field —  with low policy differentiation between candidates, refusals to withdraw, and Michael Bloomberg’s Super Tuesday strategy, leads to a drawn out primary slate, ending up with a battered moderate Dem nominee in Joe Biden. Sanders and Warren will get into each others way until it’s too late, Buttigeg will flame out nationally after good showings in the early states, Bloomberg will be too tough a pill to swallow, and the rest of the cast (Yang, Steyer, Gabbard, etc) won’t ever be serious contenders, thus leaving Joe Biden as the parties nominee. In the general election, Biden’s lack of true fans and unexciting campaigning won’t do enough to affect voter turnout, and Trump’s rabid base will give Trump a victory in 2020, likely while losing the popular vote again.

Prediction:  Trump beats Biden, loses popular vote.

Everyone on Twitter agrees that there are multiple valid ways to grow a company and that VC is neither the solution nor the devil

(just kidding)


1/2/2021 Update

Now that the year is over, we can review the predictions I made

I was wrong about:

  • Bitcoin floundering. I expected a slow decline, with the price ending the year sub 5k. Instead, it rose to $29,000. One part – “Bitcoin as currency movement isn’t happening, and the HODLers, most scarily, appear to have accepted that” has definitely turned out true. My corresponding prediction that new alt coins would take over has not. I don’t hold any Bitcoin positions (in either direction), and have no plans to.
  • Uber and Lyft stock prices. Instead of declining sharply, Uber and Lyft both ended up far above their starting 2020 prices. As predicted, these companies definitely scaled back further from their grand AI-powered ambitions this year and are focusing on profits. However, I have realized the naivety in me trying to predict specific stock targets (especially downwards).
  • The presidential general election outcome.  While Biden still has few true fans, and ran an unexciting campaign, the 2020 election saw record turnout. The turnout gave Biden the popular vote (as predicted), but also the electoral college as well.

I was right about:

  1. The Trump impeachment trial. Pelosi did deliver impeachment articles, the trial did bring no new info (as the Senate refused to call witnesses), and the impeachment vote went along party lines, and Trump remained president.
  2. Zoom stock price. Obviously COVID sent Zoom stock soaring to an unimaginable price. However, Zoom crossed $90 in mid February. Even with a lesser impact from COVID, I am confident Zoom would have had a banner year, due to their high-quality product, and strong unit economics.
  3. Snap stock price. Despite doubters, Snap had a strong year, and has definitely carved out a large enough niche that it can’t all just be copied by Instagram. They cleared my $22/share prediction easily, and are poised for a good 2021.
  4. Democratic primary results. As predicted, Sanders and Warren got in each other’s way, Buttigieg did flame out nationally after a strong initial showing, and the rest of the cast got nowhere. This left Biden as the nominee.

Goals for 2020

This post was edited a year later (on 1/2/2021), with updates on the status of these goals.


Get Healthie to (redacted)MM in ARR

We’ll get there if we have a similar/slightly better year than last year. Will be a nice milestone, and a continuance of the good, solid growth we saw in 2019.

Status: Achieved

Maintain Healthie’s profitability in 2020

Being a profitable company lets us control our destiny, and build the company we want to build. Now that we have a history of turning a profit, we should maintain that, barring any large new growth channels that prove worth pouring a ton of money upfront in to.

Status: Achieved

Spend time identifying first Angel investment

I’ve been strongly considering doing this in the past year, and I think I’m finally in the position of being able to do this (Spearhead/Indie.VC Scout programs be damned), if I find a company that I really believe in. This goal was originally “Make first angel investment”, but don’t want to commit to doing so, in case I can’t find the right company.

Status: Achieved. I made my first real Angel investment in March, into

Start sharing and building a record of my thoughts

I’ve gotten really into Fred Wilson, and other bloggers, this year, and want to start doing something similar on a small-scale myself — both for my own sake (it’s interesting to see my prior thoughts), but also to try to become a greater part of the  larger start-up community. Concretely, I want to blog twice a month, and tweet regularly, in order to end the year at over 1000 followers.

Status: Failed. I wrote 13 blog posts in 2020 (up from 0 in 2019), and tweeted a lot more, but ended up far below my quantitative goals here.


Work out 4 times a week

8/2018 to 6/2019, I was regularly going to BJJ class 4 or more times a week. Since I got my Blue belt and moved out, it’s been a lot more hit or miss, and more like twice a week. I’ve been making a lot of excuses (some of them valid), as far as class times, and other engagements, but there’s no reason why I can’t fill it in with other excerise types like running.

Status: Failed

Win a BJJ match

I went 0-3 in 3 competitions in 2018/2019. I want to do a round robin tournament (to ensure myself matches), and finally win one. I signed up for a Grappling Industries tournament on 1/18, so committing to doing that (185lbs with Gi for those curious).

Status: Achieved. I thankfully got this out of the way last January. I won 4 matches, and finished 3rd.

Try striking

I have been doing grappling for over a decade now, but have never tried a striking sport. Want to check out a Muy Thai or a MMA gym, for a trial at the very least.

Status: Achieved.


Travel somewhere I have not been to

I travelled a fair amount in 2019, but outside of NOLA (which was amazing), all were to locations I had already visited (LA, Vegas, Philly, Toronto). I want to take a trip in 2020 to somehwere that’s new and distinct (maybe Prague?)

Status: Failed. COVID threw a wrench into this.

Play a real gig

Overall, I played less guitar, wrote less music, and played less open mics in 2019 than in 2018. With all that said, guitar remained a major hobby for me, and I’d still would love to play an actual non open-mic show. I don’t care if it’s in front of two people, more important thing it’s part of a show that people are choosing to go to.

Status: Failed. COVID made this impossible, but I don’t think I would have achieved this regardless.

Have a winning poker year

In 2019, I played 28 live poker sessions (probably around 100 hours total), and finished the year a few hundred dollars down (barring any remaining sessions in the next couple days). I am unsure if I’ll hit a statistically meaningful sample size of poker playing in 2020, but regardless, would like to win money overall.

Status: Failed. I only played 5 meaningful sessions this year, and ended down a little bit.

Read 30 books

After a year-long period where I didn’t read any  books, I started actively reading again in May, and have read 18 books in the past 6 months. I want to continue this pace, and read 30 books in 2020. I mostly read non-fiction, so if anyone has any recommendations, please let me know!

Status: Achieved. I read zero books from January to March, but read 31 in the last 9 months. 

Continue surrounding myself with great people

2019 was a great year, in large part due to the people I surrounded myself with, from coworkers, to friends, to my roommates to my SO. I truly think you are the average of the five people you spend the most time with, and I want to continue to spend time with great people.

Status: Achieved. A lot of the “surrounding” ended up being via Zoom.