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“Personal Branding”

The term is fingernails on a chalkboard-level cringe for many of the best founders—mostly because it feels most of the people who spend time building their personal brand don’t actually have much there there behind it.

At best it’s boasting and at worst, it’s blowing smoke.

Which means that most of the people who actually do have the most interesting and useful experience to add to the public conversation aren’t doing so. That means the public conversation winds up feeling like a lot of hot air driven by people who crave the limelight, which tends to be an adversely selected bunch that hard workers don’t want to associate with.

Unfortunately, this has real consequences for founders. You’d like to believe the world is completely meritocratic—that you’ll put your heads down to work on your company, hit all your metrics, and just show up on the doorstep of a VC firm who will just be bowled over at the fantastic little company you’ve created. They’ll obviously see the value of what you built and will be compelled to offer a term sheet on the spot.

That’s just not how it works.

There are so many companies out there and the reality is, many of them kind of look like each other. Very few of them have standout traction—because starting a company and achieving results is more “machine driven” than ever. If you raised the same sized seed round as everyone else, you can only hire so many salespeople, put so much into marketing, and those resources can only grab so many customers in an efficient market for people’s time. Sure, maybe someone turned a $500k friends and family round into a $10mm run rate company, and that founder will automatically get a check, but for everyone else, you’re not looking as special as you think.

So how can founders differentiate?

That’s a question that relates to what VCs are actually buying into when they decide to write a check—and by the way, this goes for talent as well. They’re not buying your past history. They’re buying what you will become—because you’re there selling a ticket to the future.

That goes far beyond what your cash flow model says you’ll do. That gets right at the heart of what kinds of decisions you will make as a founder in an uncertain future. It’s all about how your brain will work, what that will mean in terms of the moves you’ll make as an executive, and the results it will drive at your company.

Unfortunately, the blueprint and operating manual for how your CEO brain works doesn’t really come off in a pitch meeting. You’re spending most of the time talking about the market, the product, the financials of the whole thing, when in reality the person across the table is trying to figure out if your brain is awesome or broken.

Talent has to make that same assessment when they’re trying to decide whether they want to work for you. They’re imagining coming into your office to explain an issue they’re having and trying to figure out whether you’ll be just reasonable, or even better, super creative about solutions, or so petty that they’ll immediately start looking for the next job.

How’s anyone supposed to figure this stuff out about you?

Well, they’d know it if you wrote a book, of course!

I’m not saying you have to write an actual book. I certainly don’t plan on writing one—but in a way, I write a book’s worth of content every year on my blog/newsletter/Substack/whatever the kids are calling long form these days. It also wouldn’t be too hard for me to put my content into a book, because, in my head, I kind of know what book I’m writing and what the table of contents is.

And what’s what I’m getting at—it’s having a mental outline of the content that would be helpful to you if you put out there. Whether it actually winds up in book form ever is up to you. In fact, writing might not even be your thing. That doesn’t matter, because content can be microchunked into lots of different forms.

So, whatever the book you’d be writing would be—be it a book for salespeople learning how to sell solutions versus product or what it’s like being a founder and a parent of a kid with special needs—you can start with a set of chapters and each of those chapters would have some equivalent number of pieces of content that would build up to it.

Let’s say you had an idea that you could break down into 10 chapters. A non-fiction book might have 60,000 words—so each chapter would be about 6,000 words.

Medium reports that the ideal read for a post is 7 minutes or 1600 words—which means that every chapter is really just 4-5 Medium/blog/long form newsletter posts. Maybe one of those is a three part series and then you’ve got just a one off one to throw on top of that.

Want to break that up into tweets and tweet threads? You can fit about 40-50 words in a 280 character tweet and a good tweet thread is probably between 6-10 tweets. Let’s call it 8, which means the average tweet thread will give you 400 words or so.

That means if you tweet a thread everyday for two weeks, you’ve got a book chapter.

Maybe you’re not much of a writer at all. Maybe you’d rather do a podcast or a video series. Well, at 125 words per minute, 48 minutes of podcasting will net you a chapter. Of course, not all of the minutes in a podcast are dense content… you’ve got intros, outros, commercials, etc… and don’t forget tangents. So, if you were actually trying to turn your podcast content into a book, it would probably take you between 2-3 podcasts to net a chapter.

The point is, rather than start out by starting at a blank page on Substack or an empty tweet, you should start with the end goal in mind.

Ask yourself the following question:

What book would serve you and your company well if you wrote it and it became a bestseller?

Now, obviously, it’s got to be reasonable, right? You can’t write the bestselling book on how to IPO your company if that’s not a thing you’ve done before—or can you?

Well, not every book is just you spouting off what you now. Most books involve research—and there’s no reason your personal brand can’t also be one that is more about being a public student than an expert. Your whole “personal brand” could be just you curating the best thinking you can find on a particular topic as you seek to become the expert on that topic.

I mean, it’s really hard to be a boastful, blowhard learner, right? No one could call you a knowitall if you’re just studying to know more. Being less authoritative and more curious is a perfectly acceptable brand for a founder—and I would argue that curiosity and the ability to learn are actually some of the most predictive traits for founder success.

You’re going to encounter lots of things you don’t know along your startup journey. The willingness to ask questions of other people to figure out how these problems have been solved before or how they’re being solved more efficiently that you’re doing now is so important. I don’t need a founder to know exactly how to run an enterprise sales team as long as they’re the kind of founder that can write the post entitled, “I Asked the 10 Top Sales Leaders the Keys to Running a Successful Sales Team and This is What I Learned.”

Just think for a moment what it would be like to be discussing your enterprise SaaS business model with a potential investor having written that post. I mean, just being the person who took the time to reach out to all those leaders to learn from them is going to give you a real leg up on your answer—because your answer is bound to be much better than it would be having not used the excuse of a post to do that research.

Plus, if that post is in your e-mail signature, LinkedIn activity feed, pinned to your Twitter profile, etc. even if the VC didn’t see it the first time around, that’s going to help a lot with your own personal conversation funnel.

This is something a lot of people don’t think about. Whenever I suggest that they start putting content out there, their first thought is, “There’s so much stuff out there, who’s going to read anything I put out?” Well, maybe no one, unless someone starts researching you. What comes up when someone Googles you? Just your LinkedIn profile? Crunchbase? The About section of your company website? Do any of those things do a great job at answering an investor’s question of how your CEO brain works and what they can count on from you in the future if they were to invest? Does it help a prospective employee understand what you, and by extension, your team, might be like to work for?

Forget about the fact that some of your content might actually make the rounds in the startup community, which would be a bonus because then you might actually source investors you’ve never heard of or talent you didn’t know was looking. Focus on the people you do actually need something from that you are putting yourself out to. What are those people finding when they poke around your internet presence? What does it say about you? You need to start thinking about those people and treating your content like “pre-reads” for your e-mailed pitch deck and subsequent meeting. Wouldn’t it be better if they already thought you were a savvy operator before you tried to make that first impression on them in the first pitch?

Well, they’re certainly going to think that if they’re sending your Medium post to their other ecommerce founders or retweeting it.

The question of what your “book” (or, rather, the aggregate narrative thread of the thought leadership you’ll be putting out over the next year) should be about depends on what kind of persona you want to portray, what your company or career needs, how senior you are, etc. That’s best workshopped with others who already put out content, the types of people you hope to build relationships with (investors, clients, talent) and also the people who take the time to get to know you.

I’ll write more on that soon, but if you’re a founder interested in building out your “personal brand” (ugh), my wife, Aja Singer, and I are noodling on some ideas on how to help people with this and we’d love to reach out when we’re ready. Fill out this form and we’ll hit you up when we’ve got something to share.