From Wall Street to Startup Success: Adam Robinson's Journey

Adam Robinson's entrepreneurial journey has been filled with ups and downs, from nearly selling his startup for $70 million to building a profitable business generating $1 million in monthly profit. His story offers valuable insights for founders on managing finances, dealing with setbacks, and balancing risk-taking with financial stability.

From Wall Street to Startups

Adam began his career as a trader on Wall Street, where he quickly found success:

"I actually had a pretty successful for a 20-something year old trading career. But these guys were they were just living this crazy life. I just could see and feel that what they were doing was more meaningful than what I was doing."

Despite the financial rewards, Adam felt unfulfilled and was drawn to the startup world after seeing friends launch Vimeo:

"I was rooming with these guys who were starting Vimeo, the video sharing website in my apartment. I actually had a pretty successful for a 20-something year old trading career. But these guys were they were just living this crazy life. I just could see and feel that what they were doing was more meaningful than what I was doing."

After the 2008 financial crisis led to a major setback in his trading career, Adam decided to leave Wall Street and pursue entrepreneurship:

"I came back there basically weren't any good jobs. I took this like job at a second rate hedge fund really and it just you know I got fired after nine months or whatever or not even I got fired after like six weeks and then that was my out."

The First Startup Journey

Adam launched his first startup with about $2 million saved from his Wall Street days. However, the journey was not easy:

"I didn't take a salary for five years. My plan was to fund this business with my brother and have somebody else operate it. But in actuality, it was the only thing that I I was like kind of working on like five different things and like this one thing worked."

After years of struggle, the business finally became profitable:

"Fast forward four years, it's like we're still making like monthly contributions to this thing. I'm wait I'm running it. It's my whole life. I'm waiting on like him to like for his wife to say that it's okay to like put in this this 25 or 50 grand. I have this thing that I say where a startup will consume every dollar near it, especially with a first-time entrepreneur."

The Near-Miss $70 Million Exit

Adam's second startup, which he started while still running the first one, grew rapidly. Within two years, he was in talks to sell it for $70 million:

"It went from I think when we started talking about a sale, it was at like it was maybe like two years after starting it and it was maybe at like six or seven million ARR."

However, the deal fell through at the last minute:

"The most frustrating part of this story isn't the fact that the buyer walked. It was when somebody got in the dude's ear like a couple nights before he was supposed to sign and he's like, 'I'm not doing this. I don't want to buy the data company. Like, I need to stick with like cleaner businesses or whatever.'"

This setback was initially devastating for Adam, who had already started spending money in anticipation of the sale:

"I had literally internalized having this money. And again, it was like such a good thing that it didn't happen because I would have bought way too much crypto and sold it all at the lows. But I just know that I would have and I'm not just I just know that that's what happened."

Lessons Learned and Current Success

Despite the disappointment, Adam now sees the failed exit as a blessing in disguise:

"It was it was very horrible. Uh but like it it kind of like my attitude changed fairly quickly because at the time I I was sharing an office with this startup called Jasper AI who like was kind of like Chat GPT before Chat GPT they but but for two years before they started Jasper I was sharing an office with them."

Inspired by Jasper AI's success, Adam refocused on growing his business:

"I'm like, well, if Dave could do it, I could do it. And that's a real thing, by the way. It's like we thought we were $3 million guys. And then I saw them I saw these guys do this who I knew very well and I'm like they're not any smarter than me."

Today, Adam's business is thriving:

"So if you add those two up it's 25 million ARR and at that point I was talking to that guy was 8 million. So it's it's tripled you know. Um we only had six people at that time. We have 40 full-time employees now. Wow. Uh but that's not really a lot for a 25 million AR company. Like not at all. Typically, it's like 150 people they have at this at this point. We have no funding. It's a really good situation. Like, we're kind of generating like a million dollars a month in in profit."

Managing Personal Finances

Despite his business success, Adam still struggles with personal financial management:

"I remember when I was 27, I read the 4-hour work week and and I was like and I went through the the dreamlining exercise and uh it was so so naive. But I remember sitting there, I'm writing down all these things cuz like a lot of what you said is it like aligns with what I was thinking. I just want like freedom of time and choice and I want, you know, whatever all this kind of stuff. I remember writing it down. And I was like, 'Oh man, when I'm making £4,000 a month, like I could never need more money than that. Like this would that would be incredible. I've got £4,000 a month going into my bank account. Like that is that is as good as it gets.' And uh yeah, it's amazing how that line that line moves and that story changes and uh and and you breeze past way way way past it and um and you're absolutely just as anxious."

He and his wife have implemented some strategies to manage their spending:

"So, so the the method that we've tried to put in place is my wife and I every month send our transactions to an accountant and we actually have him make us a P&L and we go through it. Cool. And like that's added accountability, but like sometimes we miss a month cuz like March like I was gone almost the whole month and she was gone for half of it with me or whatever."

Balancing Enjoyment and Financial Responsibility

Adam struggles to find the right balance between enjoying his wealth and being financially responsible:

"I don't think I'm doing things that will bankrupt us, but like I think that with very, you know, with with not that much different of an emotional experience, like I could have like saved more, you know what I mean?"

He enjoys certain luxuries and experiences:

"We went on a really nice ski trip this year to Aspen and like really just stayed at the nicest place and it was just you know if you were to do it inexpensively it was like 10 times more than the inexpensive way but Like it was an incredible experience and like we we spent five winters in Aspen. We got a ton of friends there. Like that was such a good use of money in my opinion."

However, he's still working on improving his financial habits:

"I want to like make a Chad GPT financial adviser, not even a financial adviser, just like a spending adviser for me and my wife that like before the credit card is activated, you have to like run it through this chat GPT and like see if it like, you know, is actually uh aligned with what we have said we wanted."

Key Takeaways for Founders

1. Be prepared for setbacks: Adam's story shows that even when a big exit seems certain, things can fall through at the last minute. Always have a backup plan.

2. Focus on building a sustainable business: After the failed exit, Adam refocused on growing his business, which led to greater success in the long run.

3. Be cautious with personal finances: Even successful entrepreneurs can struggle with managing personal wealth. Implement systems to track and control spending.

4. Balance risk-taking with financial stability: While Adam enjoys certain luxuries, he also recognizes the importance of saving and being financially responsible.

5. Learn from peers: Seeing the success of other startups in his network inspired Adam to aim higher with his own business.

6. Adapt to changing circumstances: Adam's ability to pivot and refocus after the failed exit was crucial to his eventual success.

7. Consider the emotional aspects of wealth: As Adam's story shows, making more money doesn't necessarily eliminate financial anxiety. It's important to develop a healthy relationship with money.

8. Be mindful of lifestyle inflation: As income increases, it's easy to increase spending without realizing it. Regular financial check-ins can help keep this in check.

9. Value experiences: While being financially responsible is important, Adam also recognizes the value of experiences like travel and entertaining friends.

10. Stay humble and hungry: Even after achieving significant success, Adam continues to work on improving his business and personal financial habits.

Adam Robinson's journey from Wall Street to startup success offers valuable lessons for founders at all stages. His story highlights the importance of resilience, adaptability, and maintaining a balanced approach to personal and business finances. By learning from his experiences, other entrepreneurs can better navigate the challenges of building and scaling a successful startup while managing their personal wealth responsibly.

Article created from: https://www.youtube.com/watch?v=OZ52wU3QvMs