Should You Consider Replacing Yourself as CEO?
My internal compass has always steered me strongly toward the belief that founders who can scale with their startup companies are better to back that founders who eventually need to hire a CEO. I have talked about this publicly a great deal – how I prefer “missionaries” over “mercenaries.” But lately I’m more swayed by [...]
The One Word That Shouldn’t Exist in an Entrepreneur’s Vocabulary
No. The one word the best entrepreneurs never accept. I said it. Now let me walk you through a broader story because avoidance of the word in and of itself will seem cliche. Stay with me. When I was little I had a role model for entrepreneurship – my mom. She was a natural leader. [...]
The Corrosive Downside of Acquihires
For the past 5 years or so Google, Facebook and a handful of tech industry giants have been quietly buying scores of early-stage startups for their talent. And to keep up with the Jones’s it seems that Yahoo! has now employed the same strategy. And who cares, right? A couple of tech giants throw millions [...]
The Damaging Psychology of Down Rounds
Yesterday I wrote a post about proprietary dealflow for VCs. In the article I discussed the downside of raising capital at a too high of a price and referred people to a previous article I had written encouraging founders to raise “At the Top end of Normal” as opposed to stratospheric prices. In the comments [...]
Why Early-Stage VCs Should Be Careful About Intros from Bankers
When I was new at Venture Capital I was trying to figure out the business. It was a fun period for me because everything was new and I was curious. What kind of deals should I be doing? What stage? What price? With which other investors? Should I focus on geographies or industries? Should I [...]
How to Raise Money When You’re Not in a Major VC Market
I travel the country a lot. And I am often approached by entrepreneurs in cities which don’t have a vibrant VC community. They often ask whether they have to move to SF, NY or LA to get financed. I have the same response always, “Where do you want to live? Where do you want to [...]
Two Amazing Women Setting Out on Their Startup Journey
Note: if you’re a parent please check out their website. Kara called me on a Tuesday. She was leaving IAC to start a company. “Tasha, clear some space on my calendar tomorrow. OK?” “I want you in my offices tomorrow, Kara. Does that work for you?” Kara came. She didn’t tell me she was bringing [...]
My Favorite Entrepreneur Story in a Long Time
If you don’t like it hot, use less,” he said. “We don’t make mayonnaise here.” This morning I was reading my social media and came across an article that Christine Tsai had posted on Facebook. It was about the founder of Sriracha sauce, David Tran, displaced from Vietnam when the North’s communists took power. As the son [...]
Stop Trying to Catch Lightning in a Bottle
I’m sure you’ve all heard saying derived from Voltaire, “don’t let perfect be the enemy of the good” which in a way is encapsulated in the lean startup movement and the ideology of shipping a “minimum viable product” (MVP) and then learning from your customer base. Or to borrow a simple life lesson from Gretchen [...]
How to Sell Your Roadmap Without Selling Your Soul
This is my third post in a series on Enterprise Software. In part one I covered the need for early-stage enterprise software companies to build up professional services staff to ensure successful implementation projects. This goes against the conventional wisdom of VCs. In part two I talked about how to ensure that your professional services [...]
How to Better Manage Relationships with Your VC
Just back from 2 solid weeks on the road in Boston, New York & Philly. I spent countless hours with VC firms, startups & LPs (the people who invest in VC firms). I find these trips invaluable both from a relationship-building perspective as well as stretching my mind about our industry. I ask questions, test [...]
How to Make Sure Professional Services Don’t Take Over Your Software Company
I recently wrote a blog post in which I pointed out that many investors & advisors discourage enterprise startups from having a professional services (PS) business and I think this is a big mistake. I think it’s important for enterprise startups to layer in professional services into your revenue stream. PS capabilities are important for enterprise [...]
Why Your Marketing Campaign Sucks
Creating awareness for your brand and products is one of the lifebloods of technology startups yet in a world where so many companies are being created it becomes difficult to rise above the noise. Ever notice how some companies tend to be in the press all the time and your big new product launch struggled [...]
Consequences. And The Decisions We Make. Or Don’t.
Every decision has consequences. We often don’t fully perceive the consequences because they are often hidden by the compromises that make us feel better. Every step forward requires a decision. Or the inverse – indecision. Or as I call it, “decision, by indecision,” which is insidious. It rots the core very slowly until you don’t realize [...]
The Importance of Benevolent Dictators
I believe that groups coming together to make tough decisions driven by consensus tend to make poor decisions. This is especially true in startups where speed matters and where there is a need to constantly calibrate direction and where these decisions can have existential outcomes. Should you increase your burn rate by adding 2 senior [...]
