Entrepreneurship: Murray Simser’s Journey of Staying Power and Grit

Murray, you’ve had quite an impressive career.  Can you tell us a bit about your career journey and how you became an entrepreneur?

Like so many things in life, it was by accident. I had worked at a summer job for a very successful company in Toronto. Following graduation I was offered a job there. Within 12 months of starting at that company was bought by a Private Equity firm in the Bay Area and merged with an American company from Phoenix, AZ. That led to a recapitalization of the new entity to the tune of almost a hundred million dollars. I was invited to move to the new head office in Rancho Santa Fe, California. Now remember at this stage I had NO idea what entrepreneurship meant, and even less about venture capital. That changed really quickly upon arrival in California. I caught the entrepreneurship bug and never looked back. Bottom line, I was given the opportunity of a lifetime and it changed my life. I have some pretty cool entrepreneurs to thank for that. They offered me the red pill and I took it!


How did you come up with the idea for your first company, and what were some of the biggest challenges you faced as a founder?

My first company was a group effort of 5 founders; I was the junior man on that list. It was called eAssist. Its origin is a classic case of building a better mouse trap. My first job was at a company in the tech support and customer service business (the one that brought me to California). That business was designed in the pre-internet age. We surmised that the internet would irrevocably alter the industry. So we invented what today is called CRM software.

Our biggest challenge came about after we raised $80+ million dollars and were preparing to go public. Credit Suisse had agreed to take us out. I was in San Francisco for what is referred to as the Org Meeting (the beginning of the quiet period) preparing the IPO’s registration statement for the SEC. The dot.com bubble collapsed right then. Our company’s valuation was to be in the billions. We were set to go. We pulled the offering. Our company was subsequently privately acquired. That experience was the hardest thing I ever experienced to this day. I was 28. When you lose don’t lose the lesson.

What do you think are the most important qualities for success as an entrepreneur?

Staying power and grit. You must believe in yourself above ALL others. Don’t be dumb about it either. Respect yourself enough to do what must be done, control what you can, suffer what you must, don’t take ANY wooden nickels, and stick up for yourself, even if it costs you.

Churchill said it best, “This is the lesson: never give in, never give in, never, never, never, never give-in nothing, great or small, large or petty — never give in except to convictions of honor and good sense. Never yield to force; never yield to the apparently overwhelming might of the enemy.

How do you approach mentorship and what qualities do you look for in mentees?

I give a huge amount of my time to young entrepreneurs because I believe in the adage “never underestimate those that overestimate themselves” Charlie Munger, Berkshire Hathaway or put another “Here is to the crazy ones” Steve Jobs, Apple.So naturally, what I look for in a mentee is the aggressive and earnest desire to win but it must be combined with intellectual curiosity. I do not believe in people with desire but no thoughtfulness. Tech bros need not apply. Fail fast types need not apply.


Can you speak to any specific experiences you’ve had as a mentor that have been particularly impactful?

I like to speak at University Entrepreneurship programs. I am a bit of bull in a China shop when I do. The feedback I get is that I inspire these fresh young minds in a way the Universities never could. I have never lost that bright eyed sense either. So I can meet them where they are mentally. When I see their eyes light up, I know I have done well. I have spoken at dozens of University Business Schools and early stage incubators across the planet. The very first was in your home town, at the University of San Diego.


How do you approach balancing your responsibilities as a founder with your role as a board member for other companies?

It’s easy, don’t take on boards if you can’t afford the time. Your fiduciary obligation to your startup investors doesn’t change just because you have other commitments. Officers and Directors of companies are held to a higher standard so there can be NO excuses for being unavailable or not fulfilling your commitments. Keep your commitments at all cost, no excuses!


Can you share any specific lessons you’ve learned throughout your career as an entrepreneur and how you’ve applied them to your work as a mentor and board member?

As an entrepreneur the most important lesson I try to share with mentees is that you cannot have blinders on. You must continually try to control risk by de-risking what can be controlled. So interrogate every assumption you have made over and over. Measure twice cut once as it were.

As a Board Member I am a bull in a China shop. Governance is not sitting around and being chummy with other board member. You must also interrogate what is being fed to you. Too often boards are nothing more than rubber stamps. That is NOT their function. If a board only intervenes in a crisis it has failed to meet its fiduciary obligations.


How do you think the entrepreneurship landscape has evolved over the course of your career, and what advice do you have for aspiring entrepreneurs?

I think the greatest change is the cost of entry to becoming an entrepreneur has fallen by several orders magnitude. For instance when we founded eAssist the lion share of the money was used for CapEx (depreciable capital expenses); buying servers because there were no data centres or Azure/Google Cloud/AWS companies. That meant that there were many more gates to pass through to get that money. The ones who made it really had to think about what they were doing or they would fail along the way.

That is not case today. It is almost TOO EASY to become an entrepreneur today. For $50 you can now do what cost us $20 million in the year 2000.This means that you are on your own to determine if your effort is worth the time.  


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