The journey of a founder often feels like a series of trials of worthiness. And no experience embodies this more than fundraising.

Something happened over the last 20 years. America — the nation whose foundation was built on immigration — has itself became anti-immigration. The rest of the world has seen America's achilles heel and is in attack mode.

In our first meeting, I’m focused less on what a founder says and more concerned with how they say it.

It was 2012. My cofounder and I were huddled around a laptop pitching Brad Feld, the "final boss" in our quest to secure a term sheet from Foundry Group.

One of the most frustrating experiences for startup founders is to have multiple calls with a potential investor, only to hear…nothing. Why do VCs act like this?

The uncomfortable truth is that the majority of startup ideas are fundamentally not a fit for VCs. And it’s because of the size of the market that they’re going after.

Countless stories have been written about founders using FOMO to catalyze a fundraising process to stratospheric heights. What too many founders misunderstand is that FOMO only works when applied to a well-run fundraising process. It’s not a replacement for actual investor interest.

And it’s not something you can fake.

VCs are always "looking for alpha." But what is “alpha” and where do you find it?

I was recently asked by a founder to explain why early-stage VCs ask for side letters when investing using SAFEs. “Isn’t the point of a safe that it’s a standard agreement?”

It's been nearly 15 years since I founded DataHero. To this day, I viscerally remember how I was treated by each and every investor I met. All founders do.

What exactly is a Delaware C-Corp and why do Silicon Valley VCs care so much about where your company is incorporated?

Friday’s shocking collapse of Silicon Valley bank reverberated across the tech sector while making one thing very clear:

American’s really don’t like Silicon Valley.

What does the collapse of Silicon Valley Bank mean for Canadian founders who don’t have a banking relationship with SVB? And what, if anything, should they do about it?