One of the Most Underestimated Responsibilities of a CEO

Earlier this month, I saw quite the thought-provoking tweet from Ashley Brasier.

Whether it’s a function of confirmation and availability bias or lesser-known leadership secret, I saw similar themes pop up everywhere from Phil Libin of Evernote and General Catalyst fame to Kelly Watkins at Abstract to Colleen McCreary at Credit Karma. And because of that, I thought it was a topic worth double-clicking on.

There’s the age-old saying: Leaders lead. Managers manage. And a CEO is frankly a marriage of both. While there are the canonical examples of Musk and Jobs, a CEO both leads with her/his vision but also manages expectations.

Phil Libin has this great line:

“I think the most important job of a CEO is to isolate the rest of the company from fluctuations of the hype cycle because the hype cycle will destroy a company. It’ll shake it apart. In tech the hype cycles tend to be pretty intense. At mmhmm we are very much in the Venn diagram of two hype cycles. There’s a general hype cycle around video, which is going to be way up and down over the next few years. […]

“There is also a hype cycle around early and mid stage startup investment. It’s super volatile, now more than ever, because of potential changes in the tax laws, interest rates, and inflation. So you’ve got these two very volatile areas, video and startup investment, and we are sitting right in the bull’s eye of that. This means that my most important job is to isolate the team so that we don’t float based on the ups and downs of the current. Make sure we have enough mass and momentum to go through it, meaning we don’t change what we do based on the hype cycle.

“And that takes capital, which is why we have to raise some capital to do this. It also takes understanding of where you’re trying to go and knowing where you’re going is not based on the hype cycle. You have to have a long term conviction about that. You may be wrong. The conviction could turn out to be wrong, but you’re not going to know that based on day to day fluctuations of excitement or month to month. So have a clear direction of where you are going and then make sure the ship has enough momentum so it doesn’t matter what the waves are doing, you’re still going relatively straight.”

Kelly Watkins, CEO of Abstract, also said in an interview: “People might think the job of the CEO is to make a lot of decisions, but I see my job as setting the tone for the company. People look to leaders to gauge their own reactions in a situation. So if I’m running around like a headless chicken or my tone is on a really high frequency, people graft off of that.”

Similarly, I wrote an essay a year and a half ago. On Sun Tzu and how a leader’s job is setting the tone for her/his company. In short, your team follows you and is a direct function of:

  1. How much they trust you, and
  2. How well they understand a leader’s commands (the why, the how, and the what)
    • As a caveat, one might disagree with the what, and maybe the how, but a strong team believes in the same why.

In another interview, Colleen McCreary of Credit Karma once said: “Founders, in particular, are always looking to move onto the next thing, but people don’t come along the journey that quickly. So you have to slow down to be consistent, stay on message and tell employees how they’re going to define success. Because if you don’t focus on what really matters, people will hang their hat on an IPO or the stock price as being the determinant of success, and it’s just hard to unwind.”

And why does all this matter?

As Ben Horowitz wrote in his book What You Do Is Who You Are, “Culture is a strategic investment in the company doing things the right way when you are not looking.”

Photo by Antenna on Unsplash


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Why Career VCs Emerge at Fund III

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Though I’ve spent a minute in venture capital, I’ve never raised a fund. So I’m not going to pretend I know everything. Because I don’t. Every single idea here is one I’ve borrowed from someone with more miles on their odometer in this industry.

When does an emerging fund manager turn into an emerged fund manager? I’ve always heard the general rule of thumb is by Fund III. But in all honesty, I took that for granted and never knew why.

I found out why this week. Samir Kaji has this great conversation on his podcast with Braughm Ricke of Aduro Advisors and former CFO at True Ventures. And Braughm says:

“The other [successful trait in fund managers] that we see a lot of is really having a defined strategy, and really sticking to it and executing on it. Straying away from your strategy is one of the best ways to create issues for you down the road. Yes, it might be successful and it might create returns for you today, but it will create difficulties down the road when you’re looking to raise that next fund. Because that’s what you’re selling to me at the end of the day.

“Fund I, basically what you’re selling is a promise. You’re selling a dream. You’re selling the concept around the strategy.

“Fund II, you’re selling the execution on that strategy. Depending at what stage you’re investing at, for the most part, you’re not going to have returns to be pointing to. You’re going to be selling your ability to execute on that strategy.

“Fund III, you’re selling the returns on Fund I.”

Samir then follows up: “Fund III’s are the hardest [to raise] because by then, it’s four, five, six years in and you have to show something. It is return-based.”

Phil Libin, co-founder and CEO of All Turtles, mmhmm, and Evernote, and former Managing Director at General Catalyst, in his recent interview with Tyler Swartz, said: “We don’t need scale to make a good product, in fact, it’s a distraction if you focus on scale prematurely.” In venture, your fund is your product. And like an entrepreneur, an emerging manager shouldn’t worry about scaling the size of their fund in the Fund I and II days. Stay small. Focus on delivering on the strategy and promise you made to your LPs. After all, it’s much easier to return a $10M fund than it is to return a $100M fund. Especially since a 3-5x multiple means you’re just average these days. As Mike Maples Jr. of Floodgate says, “Your fund size is your strategy.”

By the time you get to Fund III, you now have a track record of financial return (or not). And by then, you and the market should have a good idea if you have a longer time horizon in venture or not.

And even if not, many former VCs go back to the operating side of the table, armed with the knowledge, skills, and relationships they gain on the VC side.

Photo by Markus Winkler on Unsplash


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Startup Growth Metrics that will Hocus Pocus an Investor Term Sheet

Founders often ask me what’s the best way to cold email an investor. *in my best TV announcer voice* Do you want to know the one trick to get replies for your cold email startup pitches that investors don’t want you to know? Ok, I lied. No investor ever said they don’t want founders to know this, but how else am I going to get a clickbait-y question? Time and time again, I recommend them to start with the one (at most two) metrics they are slaying with. Even better if that’s in the subject line. Like “Consumer social startup with 50% MoM Growth”. Or “Bottom-up SaaS startup with 125% NDR”. Before you even intro what your startup does, start with the metric that’ll light up an investor’s eyes.

Why? It’s a sales game. The goal of a cold email is to get that first meeting. Investors get hundreds of emails a week. And if you imagine their inbox is the shelf at the airport bookstore, your goal is to be that book on display. Travelers only spend minutes in the store before they have to go to their departure gate. Similarly, investors scroll through their inbox looking for that book with the cover art that fascinates them. The more well-known the investor, the less time they will spend skimming. And if you ask any investor what’s the number one thing they look for in an investment, 9 out of 10 VCs will say traction, traction, traction. So if you have it, make it easy for them to find.

That said, in terms of traction, most likely around the A, what growth metrics would be the attention grabber in that subject line?

Strictly annual growth

A while back, my friend, Christen of TikTok fame, sent me this tweetstorm by Sam Parr, founder of one of my favorite newsletters out there, The Hustle. In it, he shares five lessons on how to be a great angel investor from Andrew Chen, one of the greatest thought leaders on growth. Two lessons in particular stand out:

And…

Why 3x? If you’re growing fast in the beginning, you’re more likely to continue growing later on. Making you very attractive to investors’ eyes – be it angels, VCs, growth and onwards. Neeraj Agrawal of Battery Ventures calls it the T2D3 rule. Admittedly, it’s not R2-D2’s cousin. Rather, once your get to $2M ARR (annual recurring revenue), if you triple your revenue each year 2 years in a row, then double every year the next 3 years, you’ll get to $100M ARR and an IPO. More specifically, you go from 2 to 6, then 18, 36, 72, and finally $144M ARR. More or less that puts you in the billion dollar valuation, aka unicorn status. And if you so choose, an IPO is in your toolkit.

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Source: Neeraj Agrawal’s analysis on public SaaS companies that follow the T2D3 path

For context, tripling annually is about a 10% MoM (month-over-month) growth rate. And depending on your business, it doesn’t have to be revenue. It could be users if you’re a social app. Or GMV if you’re a marketplace for goods. As you hit scale, the SaaS Rule of 40 is a nice rule of thumb to go by. An approach often used by growth investors and private equity, where, ideally, your annual growth rate plus your profit margin is equal to or greater than 40%. And at the minimum, your growth rate is over 30%.

For viral growth, many consumer and marketplace startups have defaulted to influencer marketing, on top of Google/FB ads. And if that’s what you’re doing as well, Facebook’s Brand Collabs Manager might help you get started, which I found via my buddy Nate’s weekly marketing newsletter. Free, and helps you identify which influencers you should be working with.

But what if you haven’t gotten to $2M ARR? Or you’ve just gotten there, what other metrics should you prepare in your data room?

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