The Hard Thing About Startups

My good friend Ori Allon recently published a an overview of the fundraising strategy employed by his previous startups and now at his current upstart Compass. Ori's first two startups were acquired by Google and by Twitter. So needless to say, very few entrepreneurs find themselves having the luxury of starting out with an $8 million seed round as he and Robert did at Compass.

I've known Ori for many years since we were both working on universal search ranking problems at Google. I advised Julpan and saw him build that company from zero, acquire top talent, build awesome tech, and then recognizing opportunity when Twitter (along with others) came knocking. And today I'm continuing to work with Compass as an advisor.

Compass has raised $72 million in their relatively short period of existence since 2012. Some may say they're overcapitalized, and maybe they are. This doesn't matter much. Ori is an awesome entrepreneur, has assembled an incredible team (starting with his CEO) and knows how to make ends meet.

Another uniquely crazy entrepreneur is Ben Horowitz. I've never met Ben, but I read his book The Hard Things About Hard Things. It's an awesome read. But for most entrepreneurs, you'd be crazy to try to emulate the way Ben runs startups. He raised a $100M+ seed round at the peak of the dot com bubble. He executed 11th hour acquisitions to save his company. He tamed executives who were otherwise thought to be unmanageable. 

Ben has some great advice on management and company culture, but as far as startup building, I'm not sure there's too much to be learned there. His style is so unique. Same with Ori. And same with many other great entrepreneurs.

Incubators like Y Combinator do a great job of paving a path for young startups to follow. YC has had a great track record, partly because they provide good advice, and partly because they're able to get great entrepreneurs through the program.

Common entrepreneurial pitfalls are well documented and fairly easy to spot. Avoiding mistakes doesn't necessarily lead to success.

But achieving success requires finding your own personal startup type, and that's hard.