VCs Don't Owe You a Response or a Follow Up

VCs don’t owe you a goddamn thing—and especially not after they’ve already met with you. That was the time they had for you. They offered a meeting—no more and no less.

The fact that you didn’t spend the last few minutes of the meeting asking for specific feedback and posing the question of whether or not the VC was going to move this forward as a champion of the deal or at least whether they wanted to schedule a next call is your failure. When you’ve got any kind of a lead—be it for selling your product or selling your equity—and you let them go with no scheduled next step, you risk never speaking to them again.

That’s your problem, not theirs.

Fundraising is Biased and Broken. It Also Works Pretty Well and Isn't Going to Change

Everything you’ve heard about fundraising—all the worst things about it—are largely true.

Yes, straight white dudes get most of the money.

Yes, biased straight white does dole out most of the money.

Yes, many of these founders are pitching dumb stuff that gets funded all the time—especially by people they know.

Yes, someone else in the Silicon Valley insiders club got way more money than you for basically the same idea, even though you were first.

All true.

Here’s the other truth: The venture fundraising process actually does a pretty good job of distributing capital to the founders with the best chance of creating big financial outcomes.

The Nicest Place on the Internet

There aren’t a lot of places you can go online that genuinely make you feel good—and that bring out the best in you…

…especially in an election year.

That’s why when you’re in a social network for over a decade and you’ve never ever seen a negative post, gotten into an argument, or never felt worse about yourself for the time you spent on it, it really stands out.

What I Learned Coaching VCs for the Last Year and What’s Next

About a year ago, I asked why more VCs aren’t using coaches.

Given the uncertain career paths for VCs, the unique dynamics around partner promotion within and across firms, and lack of clear direction on how to best spend your time on a day to day basis, it felt like investors would benefit from talking to someone who could provide some guidance.

After all, it’s something they recommend founders do.

What followed was a stampede of newly minted associates, ambitious principals aiming for partnership positions, emerging GPs navigating their firms through fundraising, and even a few experienced partners looking to optimize their time in order to compete with up and comers.

I honestly wasn’t prepared to handle the interest—and it didn’t stop. Every week, new VCs inquired about coaching even though I had barely put it out there. I wasn’t intending on making coaching my main activity, but I found it incredibly rewarding.

I coached investors to promotions, first board seats, internal personnel decisions and even a long overdue resignation.

Here are a few key things I’ve learned...

Thinking About Proximity and Optimization in a Job Search

If you’re in venture capital and you’re trying to make partner somewhere, should you get some operational experience somewhere and then come back? It’s a question my VC coaching clients ask all the time.

Yes! 100%.

You should be like Sarah Tavel. You should source Pinterest while at Bessemer, then “[join] as a "utility player" before we had product managers, and [become] the first PM at Pinterest.”

That will lead you to ultimately become a Partner at Benchmark, one of the top venture capital firms in the entire world.

Easy peasy.

Of course, you just have to find the next Pinterest, which IPO’d for $10 billion, but that’s just a small detail.

The Tech Industry and VC Case for Kamala Harris for President

If the United States is going to continue to solve tough problems with technology, we have to have the ability to collaborate—to work together as a diverse population. That starts at the top, by example.

Kamala Harris represents the best American story we can write—the daughter of two PhD students from different cultures who came here to study. She went on to serve her fellow citizens for decades in the legal system and then in national elected office, keeping people safe and fighting for justice.

She even gets high marks from her husband’s first wife, who considers her a dedicated co-parent and a valued part of her family. This is the kind of person you would co-found a startup with—not a guy who destroys the careers of just about everyone who works alongside him.

The people who simply don’t get paid by Trump comparatively consider themselves lucky.

How to Objectively Measure the "Fundability" of Your Fund

Generally speaking, I think it’s easier to answer the question, “Is this manager going to be sought after to fund the best opportunities in X space/geo/etc?” than it is to try to figure out whether an individual founder will be successful with a particular startup idea. Once you’ve answered that question, you can dive into their ability to sort through their deal flow, do deal selection and the administrative functions of running a fund. Most of the criteria I listed above is all about being someone the very best and highest potential founders want on their cap table—and that’s the most important path to having great returns.

How to Objectively Measure the "Fundability" of Your Startup

The fundraising process sucks for about a million reasons—not the least of which is that investors often lack clarity and transparency in their communication. Still, there is somewhat of a method to their madness. Because feedback is usually given quickly and somewhat dismissively due to the sheer size of the average VCs funnel, founders walk away from the process feeling like VCs didn’t quite understand what they were doing, or they don’t understand the market.

This is some of the worst thinking anyone trying to make a persuasive argument can make—that if you only fully understood me, you would agree with me.

Founders need to shift their thinking to an assumption of understanding—that investors who see thousands of pitches per year probably do understand what a founder is doing the vast majority of the time, and have simply decided that the risk/reward for investing in their company simply isn’t as good of a deal as others they’re currently looking at.

That’s a hard pill to swallow—that perhaps you’re objectively not measuring up compared to other companies. This can be the case at the very same time you’re experiencing bias, microaggressions, and discrimination.