It’s never as easy as it looks.

Paul O'Brien
2 min readJan 4, 2023


I lost $50,000, more or less, on a business started in my 20s. Hurt a lot. I’m now 4d-*ahem* and finding peace with success. Lessons learned along the way:

1. Always have income. Never quit a job or engagement until you’re confident of success. That bullshit some claim about focus is just that, bullshit; people say ‘focus’ because they’re ignorant of any other meaningful advice to give. Always, always, work while starting something.

2. It takes 6x longer than you think and 10x longer than you hope. Plan accordingly. Now, plan again, it will take longer.

3. Team team team team. Job 1, day 1, find people who agree. Job 2, every day, keep finding people who agree and will join you.

4. 90% of people won’t get it and will tell you ‘no.’ This never goes away. If you think they’ll say you suck now, welcome to being an entrepreneur. Get over that, that comes with the territory.

5. Marketing is the most important thing you do. Not promoting. Not sales. Not advertising. Marketing. Learn the difference. Marketing is how companies avoid costly mistakes and failures. Avoid it at your peril.

6. Do NOT buy into the hype. The shows, books, and local ‘startup’ thing, they’re selling something and you’re the customer.

7. Entrepreneurship is a leading cause of mental health issues and money lost; it is not for most. Be wary of anyone who is saying it’s easy or encouraging you to be one (consider why they’re encouraging it).

8. Being a startup is not about the idea. Ever. It’s about thousands of ideas, hundreds of thousands, testing them constantly (daily) and discarding most of them. Most of what you do will fail. Focus on your mission, then a vision; everything else is a pivot as fast and efficiently as possible.

9. Lastly, perhaps most important, it is NOT about finding success; it’s about avoiding complete failure. The trick no one tells you is that “fail fast” is actually very right, but not fail as in ‘quit,’ but rather as in, ‘try, and abandon things quickly.’ When 90% of everyone fails and quits, the trick isn’t trying to be the anomaly in the 10%, it’s working so as not to be in the 90%. Sounds like the same thing but it’s not! Too many founders/startups get enamored by and drawn to wins and success. If you win, stay humble; buy yourself a nicer cup of coffee and get back to work discarding failures. Most startups fail because of confirmation bias, zombie status, and listening to customers telling them the wrong things. Always, ALWAYS, think, “this is wrong, this is not good enough,” and do better, even with wins, “always better,” because you are NOT successful until you are.



Paul O'Brien

CEO of MediaTech Ventures, CMO to #VC, #Startup Advisor. I get you funded. Father, marketer, author, #Austin. @seobrien & @AccelerateTexas.