When Founders No Longer Have Any Upside

“I thought I was doing the right thing by raising more and more money, but now I’m stuck with so little equity that my upside is super limited. On top of that, the probability that we’ll ever reach the exit we need to (in my lifetime) to make this worthwhile is a long shot. What are my options here?”

The Value of Many Tiny Financial Wins

Can I get rich without an exit? There’s a chance that my startup may never be the next Facebook or Google, but does that mean I’m resigned to being the salt mines of startup life always wishing I was them? I want that good life too — so what’s my option?

The No Man’s Land of Funding

It’s becoming pretty clear we’re not going to be able to raise our next round of funding. I feel like no one is giving any clear direction about what to do from here. Do we keep waiting? Shut it down? Why doesn’t anyone ever talk about this?

How to Find Minimum Viable Happiness

I know that someday my startup can achieve all of my life dreams and make me happy (right?). But right now everything is a mess and I feel like crap. What can I do to get my head around some goals that can get me fired up again to press on?

The Risk of Trading Vulnerability for Opportunity

I’m just getting started and thinking about giving away some equity for a Cofounder and some early investment. It sounds like a lot of startups do this, but is there something I should be considering before I hand out all of this equity I won’t get back?

Stop Glorifying Hustle Porn

I’m getting inundated by Startup Hustle Porn which seems to tell me the only way to grow my startup is to work every waking hour and apparently crush things. Is this really what I’m supposed to be doing?

The Case for Growing Slowly

I wanna go fast! Startups are all about scale and speed (or so I read on Twitter) and my genius idea is no different. How could there possibly be a case for growing slowly if what I really want is a game-changing startup?

Don’t Rush into Your Second Act

I just wrapped up my last startup and I’m totally ready to take on the next one! I just had this great idea 5 seconds ago and I’m running with it! If I just had a good outcome on my first run as a Founder, my second one should be even better, right?

Beware the Absentee Landlord of Equity

I’ve got a cofounder who is leaving the company and has a huge chunk of equity. Am I missing something or do they now get the same amount of value that I’ve got except they never have to work for it again while I slave away for the same benefit for the next decade?

Startup Culture is a Reflection of its Founders

The culture of my startup is starting to head south. People are starting to get real toxic, everyone’s complaining that they are overworked, and the vibe is getting really bad. Where is all this coming from and how do I change course?