I Told You This Wasn’t Going to Be Easy!

“I have never started with a tight goal in mind. What I have always done, and to this day, still do… I see an opportunity, I wade out into the water and I try to figure out where that opportunity is going to take me. It’s a little like body surfing when you go on vacation. You go to the ocean and you know, you get out far enough away from the shore, you start to watch the waves come in and then you choose a wave and you think that’s going to be a powerful wave and then you get on that wave and you see where it takes you, and you start to navigate and negotiate your way to shore.”

“I just love the process of figuring it out."

“If you really focus on listening you will learn amazing things.”

These are some of the amazing quotes from Ron Shaich, Founder of Panera Bread and head of Au Bon Pain that can be heard on the “How I Built This” podcast. I couldn’t agree more. I have always felt the exact same thing and it’s how I have approached my own journey as an entrepreneur for the past thirty years.

For those founders/entrepreneurs/professionals in the CREtech sector, I seem to be having more and more conversations lately about how truly hard, uncertain and scary it is to be working in this space. And it’s nothing new either. I have been having these same conversations with people in CREtech for years. I tell everyone I connect with (Founders, in particular) that it’s going to be a long, challenging and frightening journey. Maybe they thought it was going to be easy. Perhaps it’s their first time being an entrepreneur. Regardless, it’s not and it won’t ever be.

As a scarred veteran of building several businesses, and as someone who proudly talks about my own failures as a daily occurrence, here are some of the things I have offered to my fellow entrepreneurs who seek my advice on being an entrepreneur in this space...

  • You will stare at the “no money in the bank” abyss many, many times.
  • Your product will take a while to gain traction (while staring at the no money in the bank abyss).
  • Your technology will break and break and break.
  • It will be virtually impossible to get attention in the marketplace among your target audience.
  • Hiring and retaining talent will always be a challenge
  • You will have many a sleepless night where you question yourself, your decisions and your strategy.
  • You will feel alone, isolated and mentally/physically exhausted.


Sounds fun right? :)

Well, if you are like me and you gravitate towards a challenge and building hard things, then embrace all of the above.It also took me a while to understand this about myself. When I look back on my own journey as a Founder, I think about when I was in my early 20’s and running my PR firm. I was FUCKING terrified every minute of every day for years! Terrified of failure. Scared shitless of running out of money and having to lay off good people. I was always in fear of the competition. And the crazy part was that I was actually thriving in business. Even though the numbers were strong as hell, I never felt secure in myself or the business.

What I realized later on was that that fear was actually my secret weapon. It’s the fear that drives many of us entrepreneurs to work harder, to be more manic and obsessive. It’s our secret sauce that ensure we NEVER EVER let up and why many of the greatest businesses in the world were started by crazy founders. You really have to be a bit crazy to see things others don’t, to take risks others won’t and to not quit when others would.

And so once I embraced my own crazy, I never thought that way again. Everything now comes so much more naturally to me as an entrepreneur. Staring at $2,000 in the bank with no idea how I am going to make payroll? No sweat this time around! Product, marketing and adoption pressures? I got this! People challenges? Well, maybe that one never gets easy.

Which brings me back to CREtech. We are indeed in this same cycle. We are in this climate where it’s increasingly challenging to raise early stage funds. And despite daily headlines about the market really taking off, we are still so early in the adoption phase of CREtech. So, my advice to fellow founders is to ignore the fearful voices in your head and instead focus on your product and listen to the market, for it will tell you where to go. Don’t worry about creating a road map or business plan (yes, I said that)! Fuck strategy and what the consultants/advisors might tell you about how you need to commit to one strategy and follow that with great precision. No! The answer lies in listening, building a small tribe of enthusiasts and constantly adjusting course.

Oh, and having the grit of a motherfucker that will never, ever quit or give up!

Embrace the unknown, the uncertainty and the craziness of it all. You are a trailblazer. Risk taker. Embrace it. Own it. And when therefore all of the hard things come you way, don’t be surprised. Embrace it as a reflection that you are in the fight we all go through. It’s ALL of our journeys, not just yours. Welcome to the club!

If only someone had told me that when I was setting out on my journeying would have saved me a ton of stress and sleepless nights. But then again, if they did, I wouldn’t have been able to write this blog and help other entrepreneurs!

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