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It’s been a little over a month since I received my last paycheck as a full-time Developer. That’s the day shit got real.

I spent over a decade building products with great people at a Fintech company. Walking away from the comfortable six-figure job was hard, but ignoring my thirst for more was even harder. The decision to leave was easier knowing I had two chatbots in Slack’s App Directory. Both with thousands of installs, tons of dedicated users, and one starting to generate revenue. The door to botrepreneurship was waiting for me to walk through.

The Start

Around this time last year I began my exploration into chatbots. I had no idea of the onslaught that would soon develop. I was spending sleepless nights learning Node.js and tireless...

Just a couple of weeks ago, I closed my first ever investment in a private Silicon Valley startup. I didn’t go through the standard procedures though: while I did conduct my due diligence, I did not get pitched face-to-face in a nice conference room, negotiate deal terms, or seal the deal with a firm handshake.

Instead, like many other educated folks who are excited about startups but don’t quite have the wealth to be accredited investors, I invested through a crowdfunding campaign.

There’s a storm of hype building around this new equity crowdfunding model, which allows middle and even working-class people to invest in a startup by the tens or even hundreds of thousands, without many of the onerous regulatory and accounting issues that so ...

Contrary to popular mythology, venture capitalists are just regular guys who make bets on big opportunities like anyone would in the stock market. They do everything in their power to make sure their bets pay off, but ultimately, even the best ones miss far more often than they hit.

While there are a handful of titles that are thrown around, such as General Partner and Principal, what matters the most is that you talk to a “Partner.”

A venture capitalist is charged with finding a relatively small number of investments (usually less than a dozen per year) to make over a 7 – 10 year period. While the venture capital firm may look at thousands of deals in a given year, they can only pick a handful of deals to pursue.

Writing Checks is Easy. Ma...

Amy Errett wasn’t the likely candidate to reinvent women’s haircare. For one thing, she doesn’t color her hair. For another, she’d never built a company shipping physical goods before.

And this wasn’t lost on her high-powered Silicon Valley network, who couldn’t quite understand why someone so “smart” was wasting her time on such a frivolous category. One they (Usually men whose wives could easily afford $400 salon treatments) just didn’t “get.”

Instead of listening to the Valley elite, Errett listened to her nine-year-old daughter who’d heard her ask countless family friends about their hair routine, whether they colored it, what they used, if they were concerned about the toxins in those treatments, the ammonia that could burn a hole in a...

##What is an operating agreement?

An operating agreement is a legal document that outlines the financial rules, responsibilities of founders, how disputes are resolved, and even more of a limited liability corporation (LLC). Other business formations, like corporations, have articles of incorporation and corporate bylaws, which are similar to operating agreements but not the same. Basically, they’re the way you and your cofounders will outline everything you need to know and do in order to successfully run your startup.

While only California, Delaware, Maine, Missouri, and New York actually require that an LLC has an operating agreement, we very, very highly recommend drafting one, regardless of where you’re located. If you decide not to h...

So much has been written about startups and founders, it’s challenging to sort through it all and make sense of advice that often ‘depends’. Here’s my guide to entrepreneurial sins from 2 decades of entrepreneurship.

Taking an honest look at your startup — never an easy thing to do.

But you must.

Being too Early

A startup needs to be early to market, to disrupt while an early market is not yet conducive to incumbent self-disruption. But being too early is often deadly. No amount of brilliant entrepreneurship will save a venture that is too many years ahead of the convergence of factors necessary for success.

How many years is too many? This depends largely on capital, but a few years of prematurity may suffice.

What makes this business sin...

In June 2013, I met the CEO of a data analytics startup here in the Bay Area. They had raised many millions already and I was on a mission to pitch them our services. However, as I stepped into their foyer, I was already filled with questions.

This was a handsome office for a company that had just raised a Series A round. Rather outsized, like a gangly teenager wearing his father’s jacket. Looked nice, but why does a small startup need a 5X office in one of the priciest real estate areas?

His answer caught me off guard. “I don’t ever want to feel cramped again!” he said, squishing his shoulders together.

Not far from this office, not so long ago, Steve Jobs had made a speech about “Stay Hungry, Stay Foolish”, and here was a company that go...

There you are: Standing at the edge of the metaphorical startup cliff. You want to cannonball into the abyss that is Founder-hood… But, you’re scared as hell that you might be jumping in too soon.

What do you do?

Are you asking yourself the right questions? How do you evaluate whether this very moment is the one to take the plunge? Are you sure?

Every startup Founder goes through this inner battle, yet few know what to look for.

While everyone’s situation is unique in their own way, there are three critical indicators that can help you determine if the timing is right— before making the leap.

Critical Indicator #1: Customers are buying — constantly

The moment you start seeing real revenue from a consistent stream of customers, it’s time to...

I believe passion is infectious, and when you get likeminded individuals in a room together, discussing real change and impact for not only a company or organization, but also an entire city, it creates a real sense of dedication.

Buenos Aires, Argentina, is not the first place that people think of when they think of startups — but that’s going to change if Lisa Besserman has anything to say about it.

Lisa’s organization, Startup Buenos Aires (SUBA), has been working tirelessly for the past few years to harness and unite the massive amounts of creative energy and technical knowledge that are floating around South America’s most dynamic city.

In just three years, Lisa and her team have not only created a resource hub for entrepreneurs in Bue...

Rich Aberman and his co-Founder Bill Clerico were making great progress with their payment processing startup, WePay.

The platform – which made it easy for small businesses, organizations and nonprofits to accept credit card payments online – had taken shape over the course of six years. Revenue was growing month-over-month. Customers liked it, the press liked it — and investors had put in a lot of money to keep growing it.

But in 2014, Rich and Bill were getting ready to kill it.

The transition away from direct business

No, it wasn’t the startup equivalent of a suicide pact. They hadn’t given up – quite the opposite. Almost without meaning to, they had landed on an opportunity with the potential to leave the direct business in the dust.

Th...