Alex Cohen knows his way around the tech industry. He's been working in startups since he was in college, and went on to co-found fintech company Birch, which was acquired in 2018 by Even Financial. Today, he works as Director of Product at Carbon Health and is a part-time investor at Bloom Venture Partners. But his Twitter feed doesn't look the way you might expect.

In a world where VCs and startup founders are often content to tweet vaguely inspiring one-liners or tout their successes in threads, Cohen chooses to do the opposite. Follow him for long enough, and you'll often see him as the loudest voice on the other side of the aisle, criticizing or mocking posts from other notable, popular figures in the industry — something which he's gotten his fair share of flak for. His Twitter bio claims one singular purpose for existing: "Here to shitpost."

We spoke to Cohen about his thoughts on the state of the discourse on Business Twitter, the state of the tech industry at large and the way it presents itself to the world.

Business of Business: You're often the contrarian on tech Twitter, and I want to talk about your thoughts on the general discourse there and why you have the stance that you do. But before we get into that, I think it would be helpful for readers to get a little bit of a background on you. Let's start at the founding of Birch and your experience with the company up to when you left Even Financial, and if any of the experiences you had during those four to five years informs the way that you see things now.

Cohen: I accidentally fell into startups is how I would describe it. The very first startup I joined was in Florida and was called Sharpspring — it was a marketing automation platform. Our claim to fame was Grooveshark. When that went under, Sharpspring was the next Gainesville-based startup to actually do something interesting. I couldn't even tell you what a startup was at the time, but I got recruited by a friend and next thing you know, The CEO made me an equity offer to stay. I was 19 or 20 at the time and was like, “No, I need to go get a big name company on my resume. I don't think this is gonna help me.” So I left and went to JPMorgan. 

And then six months later, Sharpspring was acquired for $15 million in an all cash deal. And then fast forward three or four years later, and they're now a $200 million public company. So that was probably my first mistake that I made. But I eventually came back to Sharpspring after doing the big company life. I just could not stand working at a large bank or consulting firm. I just felt like everyone was super mediocre. So I went back to Sharpspring and worked on the partnerships team. I had been experimenting with Birch before all that, and then six months later, we ended up going full time into Birch. So I quit for the second time at Sharpspring and spent four and a half years basically trying to make a better version of Mint.com.

We went up and down Sand Hill Road a couple times and got rejected by the majority of VCs, and we were raising money for the first time. Then four and a half years later, we were running out of money. So we figured out how to sell the company in a deal that sort of gave another shot on goal for the team and for investors. And then we joined Even Financial for a year — Well, I did for a year, the rest of the team stayed for two years or more. And then I just took some time off the end of 2019. I started working on some SAAS stuff that I left after it ended up taking a direction different from what I expected, and eventually got recruited by Carbon Health when I found out that the VP of Product was one of my angel investors. 

Everything about Carbon is incredible. I did a lot of diligence and sort of looking into the team and the mission and the company. And it's hands down the best most talented team I've ever worked with. We're just in pure hyperscale mode with COVID. Our core business is primary care and urgent care, and everything's just exploding. Tomorrow marks a month since joining them, which is crazy. But that's sort of the thing — I knew I didn't want to start another company. Being at three early stage companies got me to the point where I said, something feels a lot more interesting about joining a serious, C-stage or later company that's on track to have a large liquidity event or hopefully an IPO at some point. And I want to be a part of that and see things through the stage. And I'm very happy with that decision. It's been great.

Why didn’t you want to start another company? There’s always a lot of talk about how important it is to join one of these big, fast-growing companies early on, and to not make the mistake you made with Sharpspring. Could you talk a little bit more about how a Series C company one with a big liquidity event coming up is different? 

I think that there's this over glorification of early stage companies. I think normally what you see is a lot of really strong founding teams, and that makes sense in terms of the equity distribution that they have early on. But I think what ends up happening in this middle stage, and why it's so hard to hire when you're pre-seed or even through Series A, is you sort of get self selected, junior people in who are more risk seeking, but typically not as talented. That is, unless the situation is that you left an Airbnb or Stripe, and you’re recruiting a team from there. 

"I see all these threads that are like, “Give a one-liner pitch for your startup and let's get you funded!” I read through them and I’m just like — most of these companies just can't raise venture money because they're just not big enough things." - Cohen

I think for most people, if you're really really good, like, why would you join somewhere as employee number five or six and take 5-10% equity when the founders are at 40% or 50% unless you like unequivocally believe that that founder is super talented, and like you can get behind them? And I think that's rare. There are definitely founders like that — I can name a few like people who I would go join, but that's rare. 

I think there's also some arguments to be made that early stage feels so doomed to fail. Like, 90% of companies fail. If you’re joining somewhere that's in a later stage series, there's lower risk and lower reward, but it still has pretty meaningful outcomes. I like to use Snowflake and Snapchat as an example. They’re outliers, but any director that you go look up on LinkedIn who joined Snowflake two years before IPO is worth upwards of, like, $30 million. And that happened because they joined when the internal fair market value of Snowflake was probably like a $600 million or $800 million cap, and then when they went public, they just skyrocketed up to $80 billion. I don't think many people do that equation. It feels good and hot to be a part of an early team, but the math doesn't work out a lot of the time. And I think I learned that over and over again. Like, how likely are these things to fail? Why am I trying to whack-a-mole at product market fit and build something big again when there's stuff out here that's scaling and has very good potential of getting huge from the point that I join?

Could you talk a little more about what the experience of getting rejected repeatedly for funding at Birch was like? You’re putting everything into this company, working long hours, and then other people aren’t willing to buy into the thing you’ve invested so much of yourself into. What’s that like?

I think if you can't raise venture capital, you shouldn't take it personally. And I did. But you just need to look at the sheer number of companies out there. I sit on the other side of the table now, as a venture partner at Bloom Ventures, and the majority of companies we see are just not venture-backable companies. The business just doesn't scale to a point that makes venture economics work. So I hope we see more non-traditional routes of financing for companies to grow that aren’t venture. I think there are a lot of opportunities with companies that are not going to be multi-billion dollar companies. 

And that's not to say they're not going to be big companies — you can go and sell a company for $200 million and have it be an amazing outcome for the entire team. It just doesn't return the funding. I think a lot of founders are naive going into the process saying like, "I deserve to raise venture capital" when they're just not working on a big enough thing. I don't think enough founders ask themselves, “Is my company actually the right fit for what venture funds are looking for?” I see all these threads that are like, “Give a one-liner pitch for your startup and let's get you funded!” I read through them and I’m just like — most of these companies just can't raise venture money because they're just not big enough things.

Let’s start talking about Twitter. Like I said earlier, you and your feed really stand at the opposite end of this stuff that I typically see from VCs and founders — things like the “one-liner startup pitch” threads you mentioned. It’s a really broad question, but what’s your read overall on the way that this industry presents itself on social media? 

Do you mean the toxic positivity or everyone sort of fluffing each other?

I guess both. I don't want to be too harsh, because obviously these people have accomplished huge things. But I see the way people who aren't in that world react to it online as well, and I think it really frustrates people.

Yeah. So I think what I would chalk it up to is that there's very little downside to just being overly optimistic and nice and patting everyone on the back. And I think that’s boring. I think it's the safe way to be a human being on the internet. 

I'm not gonna call out anyone specifically. But there's definitely people who I just can't follow because they're overly positive and optimistic and not realistic. And it's just — it's really annoying. And I find it just disingenuous. I think that's how it comes across to me and a lot of people who don't work in tech — like people are scared of calling each other out.

I guess I bundle it all up into shitposting, which is what I call most of my tweets. But I feel like there's competitive advantage to being just genuine and authentic. My genuine personality is I just question everything. I'm typically skeptical of things, and I call bullshit when there's bullshit. I've never really shied away from that. And I think about that sometimes — like, “Am I being too negative on Twitter?” But then I get messages like one yesterday from a friend, who is an amazing founder, and she's like, “I literally unfollowed everyone except for you. You make the toxic parts of Twitter bearable.” I thought that was hilarious, but also kind of sad.

My feed definitely attracts a certain kind of person. I've met so many people in real life off of Twitter, and it’s really only been like a year and a half of me tweeting a lot. I think I just leaned hard into, “I'm just gonna tweet my authentic thoughts and be my genuine self on Twitter, and it'll attract people who want to follow me and engage with my tweets.” And for those that it doesn't resonate with, like, I don't really fucking care, it's the internet. I think that has led to a lot of really great real life relationships where I meet people for coffee or drinks. Even during the pandemic I'll get outdoor, socially distanced coffees with people. It's led to a lot of good relationships, because we typically have things in common versus, you know, other people who are just spewing out platitudes on the internet. Sure, they're sure they're going to attract a large audience and cast a wider net, but I don't really want those people following me because it doesn’t add any value to my life.

I don't mean to do a psycho analysis of shitposting — I post dumb things on Twitter all the time. But on some level it’s definitely a reflection of things I actually think. Would you say that your feed is a kind of reflection of you wanting the industry to change or act differently?

I mean, I don't tweet with the expectation that  people are gonna follow suit. I just tweet the way that I want to tweet and walk to the beat of my own drum. That's it. People are going to keep doing what they’re doing. You can't change people and who they are. But I get a lot of messages — like a weird, strange amount of messages — of people that say like, “I love following your Twitter because it's so honest and refreshing.” If I’m trying to overanalyze people, I think they’re afraid to be authentic on Twitter. 

"I'm definitely wanting to push back against things like when someone who's got 300,000 followers says “Everyone should go start a company.” Like, no, that's fucking bad advice." - Cohen

Online, people forget everything a week later. And whatever I post — as long as it's not, you know, really terrible shit that's going to get me cancelled — most people will just forget about a week later, because everyone has so much going on. And I kind of tweet with that mentality. A few nights ago I posted about fund economics and math with a very simple spreadsheet. And I didn't even think twice about what numbers I put in there for company valuations. And I was like, "Look at that — if you invest at two x evaluation, you get half the return." And everyone's like, yeah, no shit, that's algebra. And I'm like, Yeah, I guess I didn't post this with the expectation that everyone's gonna rip it apart like that. But I figured in a week, no one will remember that that exists. 

That feeds back into what you were saying about the human interactions and friends you’ve made through Twitter being more important.

Yeah. That's more important to me than being right all the time or trying to prove that I'm smart on the internet. There's demand for whatever type of Twitter post category. There's demand for platitudes, for tech drama, and for hyper positivity. And that's fine. I mean, people will follow what they like.

But yeah, I do think I'm definitely wanting to push back against things like when someone who's got 300,000 followers says “Everyone should go start a company.” Like, no, that's fucking bad advice. Someone needs to say something because, like, you really shouldn't do that. I also hold sort of a personal thesis that if you need to be told to go start a company and that's your motivation, you probably shouldn't be going and starting a company. Those things are pushed from within versus being pulled out. So I push back when I see dumb tweets like that that are just really bad, generalized advice. 

But I don't want to be just negative - There's a lot of really great advice on Twitter.

Since we’re on that topic, who are some other people whose feeds you really enjoy or you recommend others follow? You said you didn’t want to call anybody out, so how about a few shoutouts?

Oh yeah, I will definitely call people out in a positive way. There's so many people who are actually posting really in-depth, good tweets. Austin Rief, who is one of my old angel investors, started to share more of his learnings from running Morning Brew and building it into an $80 million company. He's very authentic with the way that he describes the stuff that he's learned. 

Lenny Rachitsky, who used to be at AirBnB, went and started a newsletter and writes a lot about product. And that stuff is really good and really authentic to what he knows and understands. Shreyas is also great. I think he was the first product manager, or director of product, at Stripe. He tweets these elaborate threads about product management and I love it. It’s something that I like to follow. Elizabeth Yin from Hustle Fund is another. Her tweets are really good. She's super authentic and open and transparent about the way that they're building Hustle Fund over there, so I follow and retweet a lot of her stuff as well. 

So anyway, there's really good people to follow on Twitter. You just have to curate it. And maybe one of these days I’ll actually put together a list of my favorite people to follow on Twitter. But, you know, that takes effort.

Is there anything else that we didn't touch on that You'd want to mention?

I'm 50% scared and 50% excited. I haven't really spoken publicly about my thoughts on Twitter and tweeting, and just generally about the tech industry. I think everything I’ve mentioned probably describes why I post the way that I do on Twitter. Why I'm not really afraid to get into arguments with people. Because I believe that people will forget things a week later.