A Nerd in a Football School
In the Fall of 1980, I had it all figured out. I was a Junior at Medford Senior High School, the big leagues. My GPA was perfect and I was looking forward to my AP classes, science club, and the debate team. I grinned when I found my locker, #B69. Chad, the Varsity football captain grunted … Continue reading A Nerd in a Football School
Karma is real
I received a message on LinkedIn yesterday. It read: Martin! It has been like 23 years since we met in Silicon Valley. I so enjoyed our connection. You still in digital media? How have you been?” A couple clicks reminded me of our connection and the memory popped into my head of a couple of … Continue reading Karma is real
Reframing a guiding principle today.
“I hope you don’t get what you want in life, because then you are Fucked.” Martin Tobias For over 20 years, this phrase has been one of my guiding principles. Today I am softening it. Why soften it? I want my guiding principles to be in the positive frame, not the negative. While this has … Continue reading Reframing a guiding principle today.

Finding out about ROAM
Pretty much my experience so far. finding out about roam… from r/RoamResearch

My Angel Investment funnel
Over 8,000 companies received pre Series A funding in 2019. 2020 is on pace to surpass that. How does one separate the signal from the noise? Over 25 years of Angel Investing, I have made every mistake there is and built a process from all that learning. This is the process I use to select … Continue reading My Angel Investment funnel
My Meta Investment Themes
In addition to being asked how I decide to invest, I am often asked WHERE I look for investments. The short answer is where I have an ADVANTAGE. Some kind of information, insight, or talent advantage that is not available or at least non-obvious to others. The long answer is the rest of this post. … Continue reading My Meta Investment Themes
Remember Martin: There is nothing to believe
Why do I find the Stoic frame for answering the “how do I live my life?” question so useful? There is nothing to believe. No pretend friends. No magic underpants. No invisible hand. There are questions to examine yourself and others on the path to wisdom. There are practices which over time can reveal wisdom … Continue reading Remember Martin: There is nothing to believe
How I decide on Angel Investments
I have invested millions of dollars directly in over 100 startups over the last 25 years. Many more through Venture funds and other syndicates. I am often asked how I decide to write the check. Well here is my process which has produced a 3.5X return on capital (so far). This is my process for … Continue reading How I decide on Angel Investments
How much money should I raise?
This is a question that I get multiple times a week talking to CEOs of startups. Having raised over $500M for my own startups and invested in over 100, here is my best advice. Decide the two or three most important measurable questions your company has to answer in the next 12 months, calculate a … Continue reading How much money should I raise?
Glossary: Assume
One of my first memories of wisdom, an eternal truth that run true and would be useful over time, came from my high school debate teacher, Terry Rose. “Never Assume anything.” Terry said, “It makes and “ass” out of “u” and “me”.” The poetic ring to the quip helped it stick all these years. Oxford … Continue reading Glossary: Assume
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