Mentoring Entrepreneurs: My Mindset When Raising Capital

The topic of raising capital has come up a lot in my mentoring sessions. While I am certainly not an expert on raising capital, I have raised 8 different rounds of capital across my 3 companies. So I thought that it would be helpful if I share my mindset. Any VC or Founder friends reading

Mentoring Entrepreneurs: Breathe through the Pain

I mentored a very compelling entrepreneur last night. She has a great background and has built a compelling v1 product in a massive market with little competition. In my view, she is on the precipice of greatness. She asked for mentoring time because she wanted to talk through a business challenge. The challenge was so

Mentoring Entrepreneurs: Why Customers Don’t Purchase

I had a great mentoring conversation with Boyede Sobitan. He is the Co-Founder & CEO of a startup in the food delivery space, OJAExpress. His business offers food delivery for specialized grocery stores. It is a very interesting business idea for a number of reasons, including what should be a customer base with great word

Mentoring Entrepreneurs: Customer Financing

I am passionate about entrepreneurship. I truly love it. And I deeply believe in equality in our society. And so I decided to put those two beliefs together when I sent out the below tweet:   Before I hit send on the Tweet, I thought that I would only get a few responses. I do

Lessons Learned from Startup #3

Wow, it has been a long time since I last blogged here. Guess I got so wrapped up in my last company that I didn’t have time for blogging. But since I sold Validately in June, I now have time to share my thoughts on entrepreneurship.  I will re-enter the blogging world by sharing my

Why a Founder Sells

I had a “conversation” with Keith Rabois yesterday on Twitter about why a Founder sells his company.  Our conversation was in a response to a blog post by Bijan Sabet in which Bijan makes the case that selling a startup allows a founder the opportunity to create something new. Keith responded that founders only sell

What @Dens can teach John Boehner

The shut down of the US government is a great case study for Product Managers and Entrepreneurs. It is a case study on signal vs noise. Power Users There is no doubt that all Congressmen have a very loud and ardent set of “customers.” Pick the issue, and you have passionate believers on both sides.

How To Avoid Being The Idiot

I wrote last week that there are three categories to any market: the Innovator, the Imitator and the Idiot. This pattern happens over and over again. Once a product shows success, rational people follow with a 99% similar product, aka a “me too.” And while it may be rational, it is a stupid decision. The

The Innovator, The Imitator & The Idiot

There are three “I”‘s of every product category: the Innovator, the Imitator and the Idiot. You can clearly see this pattern in any product category. Why it Happens There are many reasons that products follow a herd mentality. – Strategic reasons (ie to cover a flank). – Desperation (ie we are failing and have no

What Scares A Founder The Most

Founders take a lot of risk. They constantly live on the edge of failure.  It gets a little better after achieving product-market fit.  But before then, you are doing a dance with failure.  And during this highest risk period there is nothing that scares founder more than…False Positives What’s A False Positive? False positives come