How Entrepreneurship and Networking Are Synonymous With Each Other

A few days ago, I came across a question on Quora that sparked my interest. “What [is] the best network for developing entrepreneurship skills?” And I couldn’t help but backcast, as Mike Maples Jr. at Floodgate would call it, which I shared a bit more here. Looking at the entrepreneurs I know who have achieved some modicum of success, how did they build their entrepreneurial skills?

Taking it a bit further, what is one skill that they have that made all their other skills much easier to acquire and/or hone? And I could only come up with one answer, which is understood in various nominations. Resourcefulness. Scrappiness. Creativity under pressure. Staying lean. Frankly, their ability to hustle.

“The best network”

What is the best network for developing entrepreneurial skills?

The simple answer: One you build yourself.

The longer answer…

Entrepreneurship is a career that requires you to hustle. Likewise, a network you build yourself from reaching out and cold emailing has the potential to be stronger than even the best of networks out there. But entrepreneurship can come in two flavors: a hobby and a lifestyle.

A hobby or a lifestyle?

If entrepreneurship is a hobby, there are amazing collaborative:

  • Slack groups,
  • Subreddits,
  • Facebook groups,
  • Quora spaces,
  • Meetup groups,
  • Conferences/trade shows/expos,
  • You name it, it’s out there.

But it will be akin to sitting in a classroom and learning the theory and conceptualizations.

If entrepreneurship is a lifestyle, you need to learn by application. And unfortunately, you’ll need to develop scar tissue from making real mistakes outside the classroom. You need to hustle and find what works and doesn’t work for you. Two of my favorite venture firms, 1517 Fund and Hustle Fund, invest in founders who do exactly that. Unlike many other venture funds, it’s in their thesis. Learn by doing. Learn by hustling. While there is merit in literature and academic institutions, you are learning at the pace of the system. And when you’re a founder, often times, time is not on your side.

In a parallel, an entrepreneur once described the bifurcation as a “lean-back” versus a “lean-in” activity. A “lean-back” activity would be watching a sitcom, picking strawberries, or typing a simple response to an email chain. Whereas a “lean-in” would be playing football, playing a competitive first-person shooter game, or fixing a bug in the code 2 hours before a product launch. Entrepreneurship, as you might guess, is a “lean-in” sport. So is networking.

There are two French words I often allude to – savoir and connaître. Both mean to understand. Savoir means to understand on a superficial, factual level. Connaître means to know on a deeper, emotional level – to be deeply familiar with. As an entrepreneur, the lifestyle you choose is often not passive, but an active one, or some might argue, an aggressive one. One where the clock started ticking before you started. Sometimes, before you were even born. Ben Horowitz makes a brilliant comparison between a peacetime and a wartime CEO. From his piece, I’ll quote two of his juxtapositions:

“Peacetime CEO knows that proper protocol leads to winning. Wartime CEO violates protocol in order to win.”

“Peacetime CEO has rules like ‘we’re going to exit all businesses where we’re not number 1 or 2.’  Wartime CEO often has no businesses that are number 1 or 2 and therefore does not have the luxury of following that rule.”

Where you’re required to make decisions in difficult times, and if you don’t understand a concept or a skill to the level where it’s engrained in your bone, you will fumble more often than you run touchdowns. Part of the reason why second-time, third-time entrepreneurs usually perform better than first-time entrepreneurs.

I graduated from a stellar university, UC Berkeley, located at one of the epicenters of Silicon Valley/Bay Area, where I got my economics degree and a certification in entrepreneurship and technology. I took a number of classes that allowed me “to learn and hone” my entrepreneurship skills. While there were a handful, I came out feeling I was equipped with the knowledge to take on the world. When I put them to the test, I realized I knew nothing. When faced with reality, I didn’t know how to deal with edge cases since edge cases are rarely taught in the classroom.

Most communities and classes teach entrepreneurship skills in abstractions, making it easier to understand. Even this blog post is, in many ways, an abstraction. They rarely teach the edge cases ’cause frankly, there are too many “what if’s”. But as an entrepreneur, you need to be ready for the “what if’s”. For anything and everything. And over time, what transcends the individual skills you have is having a mental model to hedge yourself from future edge cases.

I once asked someone what being an expert meant. And I really liked his answer, as it stuck with me all these years. He said, “An expert is someone who has made all the mistakes in a very narrow field.”

Photo by Jed Villejo 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!

Part-time vs. Full-time Founders

Over the weekend, my friend and I were chatting about the next steps in her career. After spending quite some time ironing out a startup idea she wants to pursue, she was at a crossroads. Should she leave her 9-to-5 and pursue this idea full-time, or should she continue to test out her idea and keep her full-time job?

Due to my involvement with the 1517 Fund and since some of my good friends happen to be college dropouts, I spend quite a bit of time with folks who have or are thinking about pursuing their startup business after dropping out. This is no less true with 9-to-5ers. And some who are still the sole breadwinner of their family. Don’t get me wrong. I love the attention, social passion, literature and discourse around entrepreneurship. But I think many people are jumping the gun.

Ten years back, admittedly off of the 2008 crisis, the conversations were entirely different. When I ask my younger cousins or my friends’ younger siblings, “what do you want to be when you grow up?” They say things like “run my own business”, “be a YouTuber”, and most surprisingly, “be a freelancer”. From 12-yr olds, it’s impressive that freelancing is already part of their vocabulary. It’s an astounding heuristic for how far the gig economy has come.

Moreover, media has also built this narrative championing the college dropout. Steve Jobs and Apple. Bill Gates and Microsoft. And, Mark Zuckerberg and Facebook. There’s nothing wrong in leaving your former occupation or education to start something new. But not before you have a solid proof of concept, or at least external validation beyond your friends, family and co-workers. After all, Mark Zuckerberg left Harvard not to start Facebook, but because Facebook was already taking off.

Honing the Idea

The inherent nature of entrepreneurship is risk. As an entrepreneur (and as an investor), the goal should always be to de-risk your venture – to make calculated bets. To cap your downside.

Marc Benioff started his idea of a platform-as-a-service in March 1999. Before Marc Benioff took his idea of SaaS full-time, he spent time at Oracle with his mentor, Larry Ellison, honing this thesis and business idea. When he was finally ready 4 months later, he left on good terms. Those terms were put to the test, when in Salesforce’s early days, VCs were shy to put in their dollar on the cap table. But, his relationship he had built with Larry ended up giving him the runway he needed to build his team and product.

Something that’s, unfortunately, rarely talked about in Silicon Valley and the world of startups is patience. We’ve gotten used to hearing “move fast and break things”. Many founders are taught to give themselves a 10-20% margin of error. What started off as a valuable heuristic grew into an increase in quantity of experiments, but decrease in quality of experiments. Founders were throwing a barrage of punches, where many carried no weight behind them. No time spent contemplating why the punch didn’t hit its mark. And subsequently, founders building on the frontlines of revolution fight to be the first to market, but not first to product-market fit. Founders fight hell or high water to launch their MVP, but not an MLP, as Jiaona Zhang of WeWork puts it.

In the words of the one who pioneered the idea of platform-as-a-service,

The more transformative your idea is, the more patience you’ll need to make it happen.”

– Marc Benioff

As one who sits on the other side of the table, our job is to help founders ask more precise questions – and often, the tough questions. We act more as godmothers and godfathers of you and your babies, but we can’t do the job for you.

The “Tough” Questions

To early founders, aspiring founders, and my friends at the crossroads, here is my playbook:

  • What partnerships can/will make it easier for you to go-to-market? To product-market fit? To scalability?
  • What questions can you ask to better test product feasibility?
  • How can you partner with people to ask (and test) better questions?
  • What is your calculus that’ll help you systematically test your assumptions?
  • Do you have enough cash flow to sustain you (and your dependents) for the next 2 years to test these assumptions?

Simultaneously, it’s also to important to consider the flip side:

  • What partnerships (or lack thereof) make your bets more risky?
  • How can you limit them? Eliminate them?

And in sum, these questions will help you map out:

At this point in your career, does part-time or full-time help you better optimize yourself for reaching my next milestone?