Tag: career

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DGQ 19: Does the overall level of the team make me question if I’d be a good enough to play in this industry?

“I won’t forget the first time I saw Jason Peters do a one-on-one pass set with Trent Cole, and being amazed at the speed, balance, and power I just witnessed. It reminded me, or looked like, a grizzly bear wrestling a panther. It was so impressive, it made me question if I was good enough to play in this league.”

Much of this DGQ was inspired by Jason Kelce’s retirement speech, delivered with the prose and candor befitting of a legend. Which for those who have yet to read/listen to it, it’s 24 minutes that will be well-spent, whether you’re a sports, football, or Eagles fan or not.

There’s something really special about being the underdog. Whether you feel it or others say it. That slight chip on the shoulder, that measured level of imposter syndrome, is fuel to the fire. There is a distinct advantage for being the dumbest person in the room, knowing that there are mentor figures on the team you can learn voraciously from, even if by osmosis. And if you do have naysayers, you have the greatest privilege to prove them wrong. It means that you have space to grow. That journey ahead, at least for me, is quite exciting.

After all, in Jason’s 2018 Super Bowl Parade speech, he quoted another line from Jeff Stoutland. “Hungry dogs run faster.”

Although not framed nearly as eloquently as Jason Kelce put it, it’s something I think about a lot. Does the overall level of the team make me question if I’d be a good enough to play in this industry?

Challenge is as scary as it is thrilling.

Similarly in VC, we often say it’s an apprenticeship business. And it’s true. Almost every great investor I know had someone who took them under their wing and showed them the ropes. Sometimes a set of people. And it’s incredibly hard to learn and check your blindside without someone who plans to dedicate a good portion of their time to do so. That said, the next best you can get is to learn by osmosis.

You are the average of the five people you hang out with most. So if you have the chance to live and breathe alongside people who intimidate you with their skill, intellect and the way they execute in a good way, take it.

Photo by Vicky Sim on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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The Tale of Two Risks: Market and Execution

market, flea market, farmers market

Folks coming out of school and/or are still in school often ask me how they should break into venture. It’s surprisingly a timeless question. The goalposts change every era. And as the signal-to-noise ratio and regression line oscillates in bull and bear markets, young professionals chase a moving target.

That said, while my opinions will likely change when the facts change, as of now, this is my best proxy for a timeless answer. Market risk versus execution risk.

Let me elaborate.

Early in your career, you should take market risk. Bet where others are not willing to bet. Or have the same starting point as you do. If the starting line is even, it’s all about how much faster you can run compared to your peers. And if you can outlearn them, ideally because of internal drive and motivation, you’ll be the incumbent in the space in the future.

Execution risk is what you pursue as you grow. Your network, your expertise, and your experiences make you a more robust executioner. You’re an incumbent. You’re a juggernaut. There’s no reason to focus on this risk when you’re younger because you don’t have an unfair advantage here. In fact, you have an unfair disadvantage. Others more senior to you have a better network, more expertise, and have done more reps than you have.

Steve Jurvetson recently shared the only rule of business that is inviolate. “Take any company that is large or top three in their industry. They will never lead the charge to disrupt that industry.” He goes on to say, that even in recent years, Google didn’t fight to change search until OpenAI. Apple is innovative outside their core business, but never in their core business. So as a result, innovation needs to come from the bottom. People who are willing to take market risk.

Similarly, in venture, as a young VC, you need to build your own thesis. For as long as you are investing on the basis of someone else’s thesis, you are competing on execution risk. And every VC who’s older, wiser, and more connected than you are on that thesis will out-execute you.

So… the risk you have to take is betting on a brand new thesis. That no one else is pursuing. No one else is investing by it. And that… is market risk.

The above is no less true if you’re an emerging GP. Your fund lacks the resources, likely the connections, the experience, the talent, and the ability to out-execute your incumbent on your incumbent’s thesis. The solution is to just not play when they have the home field advantage.

It’s why thesis and the question “Why does another venture fund need to exist?” matter so much to LPs betting on new fund managers.

Photo by Kayle Kaupanger on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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#unfiltered #58 The Shortcomings of Resumes

resume, computer, laptop

The goal of any professional in today’s economy is to never have to submit another resume ever again.

I swear this isn’t an original line, yet I can’t recall the person nor the setting in which I was told. Nevertheless, whether this was a lucid moment or not, it has been firmly etched into my pre-frontal cortex for years.

Building in public and growing under public scrutiny – be it on Twitter or a blog or another form of social media – is one of the best ways to build rapport and credibility. It’s a photograph. An imprint. Still, and in many ways, permanent. A record that you and others can revisit and reasonably objectify your personal growth. Those data points tell a story. Either you connect those dots personally, or often times, someone else connects them for you.

“We are all the unreliable narrators of each other’s stories.”

If you’ve been following my blog over the past few months, that line will carry a familiar scent. My favorite and the first line I heard from the best film I watched this year, In and Of Itself. When my buddy DJ recommended it to me, he told me only two things:

  1. It’s about identity.
  2. And, “we are all the unreliable narrators of each other’s stories.”

It’d be a travesty if I spoiled the plot now. The best way to watch it is, like most unforgettable experiences, going in blind. No summary, no trailer. If my word means anything, it’d be my answer to the question: What is the one movie you’d recommend someone who just time travelled 50 years from the past to catch up with the way people in 2021 think?

But I digress.

Street cred is built up not by what you say about yourself, but by what other people say about you. That street cred will benefit you much more than a sheet of paper that summarizes your entire career into a single pager with 12-point font. I wrote a blogpost recently on how a pitch deck fails to summarize the motivations, the story, the wins and the losses behind building a business. So, you should always be fundraising. Always be selling. Always be pitching. And as you build champions around you, they’ll tell your story – by referring you to investors, share your product on social media, and sell you for you to their friends. Analogously, a resume for a job seeker echoes the same shortcomings a pitch deck has for a founder. Job-seeking sucks. Just like how fundraising sucks.

If only life were simple

Every person has a story. If not multiple stories. We are each a product of more than one storyline. A narrative in hindsight, when we willingly choose to ignore 99% of the other facts.

One of my favorite internet writers, Max Nussenbaum, recently wrote something quite profound. “We tell ourselves stories in order to live, but our lives aren’t actually stories. If they were, they’d be poorly written ones: just a bunch of stuff that happens, with no coherent structure or consistent thematic underlines.”

There’d be far fewer cases of self-doubt and depression, if life was as straightforward as a movie script. But it’s not. And neither should it be. It’s messy. But that’s great. Because we can connect the dots however we want.

There are many ways to tell a story. And the best stories are told by others.

And yes, the goal of any professional in today’s economy is to never have to submit another resume ever again. Frankly, after a certain threshold of rapport, you won’t need to.

Photo by Glenn Carstens-Peters on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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#unfiltered #19 The Goal of Job-seeking

job seeking

Last night, I caught up with an old friend who has a few more miles on his career odometer than I have. And he shared something quite profound.

“The goal of job-seeking is to never have to submit another resume again.”

In frankness, I’ve never thought about job-seeking in that context. But it makes complete sense. You perform so well in each position that your (former) co-workers start spreading the word about you. “If you need help with [insert subject matter], you have to work with [you].” Effectively, you’re building virality around you through each ‘customer’ interaction being amazing.

And the more I thought about it last night, the more parallels I found. For founders…

The goal of an entrepreneur is to never have to pitch to investors again.

For investors…

The goal of an investor is to never have to pitch how awesome or founder-friendly their firm is to LPs or a potential investment.

And taking a step back, looking at this through macro-lens…

The goal of any professional is to never have to sell again.

You may neither be a startup founder nor a salesperson, but I believe any of us could appreciate the contextualization of our own efforts. What is your endgame? And how can you pave the the most scalable road to your success?

There’s a saying that luck only gets better with success. I’d like to believe that after you reach critical mass and word-of-mouth, you manufacture your own luck.

Photo by Avel Chuklanov on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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