A big mistake I’ve made as a founder is treating the successes and failures of my startup as a reflection of my own self-worth.
When things go great I feel great, when things go wrong I feel like shit.
I believe this causes a lot of stress, it is a source of bad-decision making and damages your leadership.
Startups navigate constantly on the edge of both extremes, success and failure.
Keep your mind healthy and pour your heart in. Don’t let the current status of your business dictate how you feel or what you are worth.
Founder burnout is the most serious threat to a startup. Protect yourself from burnout like you would protect your servers, database or premises from hackers or burglars.
The earlier in a life of a startup the more important the founders are to its success. Most of the early-stage investors invest in people. So it is pretty much an obligation to take care of yourself if you receive funding.
When founders of our portfolio can’t sleep and ask us for advice we encourage them to hire a life or executive coach and have their startup pay for it.
The ROI of good sleeping is great and for that reason I think it is an investment. A good sleep brings productivity and creativity which are essential to boost a startup’s growth and to thrive in difficult times. …
One of the golden rules (or clichés) in early-stage investing is to ‘invest in people’.
I’ve found this rule is easier said than done. Most people like to see themselves as successful individuals whose sum of life decisions (good and bad) have brought them to a good place. I am no exception.
A problem many tech startup founders face is meeting with investors that have different backgrounds.
For example, it is hard to convince a business-oriented investor about a technical breakthrough. Especially if that breakthrough has no sustainability path or interesting market size to address. 
I think it is. Limiting ourselves to our vision might prevent us from finding interesting opportunities or people. …
The tone about Grooveshark and Secret (update: and now Homejoy) shutting down sounds a lot like they failed but, did they?
Grooveshark was around for almost 10 years and was a pioneer in online music streaming. Secret and Homejoy made millions of users happy for a while. Both made something people wanted, and this is something only a small percentage of startups achieve. 
What if Facebook shuts down in five years? or Airbnb? Would Mark Zuckerberg be a story of success or one of big failure?
The lesson I see here is that success is subjective, transitory, nonlinear and mostly a state of mind we choose. …
Two amateur mistakes I’ve made (and still make sometimes) is getting too excited about deals:
To avoid this, I now try to make myself some questions and be honest with my answers before making a decision with my partners.
The good thing about these questions is that they are inversely useful for founders to assess the quality of their investors.
Do I or one of my partners know the industry well? …
Investing in payment plans happens often in emerging markets. However, it is a terrible term for a startup to accept. Counterintuitively, it is also one of the worst terms for an investor to ask for. 
Many things can happen in the life of a startup during that payment plan period. Most commonly, a startup starts to fail. The founders fight, growth ceases and employees leave. Momentum is lost, the hype is gone.
Legal implications aside, this is when investors with pending payments face a big dilemma. From a financial point of view, it is not a smart decision to continue to invest in a dying startup. …
Early startup employees often find it difficult to determine a fair stock compensation for them. 
A good way to do it could be if early employees asked founders some of the same questions investors ask before investing. In other words, they should see themselves a bit more as investors. 
When did you last raise money and what was the last valuation of the company / cap of the convertible instrument?
The answer to this question is a good parameter for early employees about the current value of their stock or options. It helps to find out how much it was worth months before when the startup raised money and how much it is worth today. …
Are you a 100% sure you will be selling the same products or services twenty years from now? I love this Brian Chesky’s quote in a letter written to his Airbnb team “Don’t fuck up the culture”.
“Our culture is the foundation for our company. We may not be remembered for much after we are gone, and if Airbnb is around 100 years from now, surely we won’t be a booking website for homes.”
Investing in startups is not about charity. It is not philanthropy either. It is not about ROI. And for God’s sake it is not about PR or marketing. …
Startups are hard for many reasons. Rejection is one of those.
Getting rejected is a natural thing in startups. You get judged by the market, by investors and even by your family sometimes.
Why is it hard for some people to deal with rejection? Because we all pour a lot of effort into building a product. Even if it’s not that good or beautiful yet, having that creation of yours rejected may sometimes feel like a personal thing. 
At a deeper level I see two underlying reasons. Arrogance and low-self esteem. The former is taking yourself way too seriously. …