In May 2019 Izzy Lugo, Co-Founder and COO at Urban Misfit Ventures, joined me on Episode 119 of the Screw the Naysayers podcast. Izzy is also a public speaker and co-host of the Strange on Purpose Podcast. 

Urban Misfit Ventures is a holding company that owns one of Milwaukee’s fastest growing startups. IEEG, a Content Marketing firm as well as an events company called the mkemisfits.

Izzy is also a huge foodie, sneakerhead and sports fan. 

Here are  7 truths that Izzy shared about his experiences as a startup entrepreneur (along with my own comments).

#1 Entrepreneurship is addicting! 

Making the switch from corporate employment to entrepreneur doesn’t have to be a one way street. But for people like Izzy and myself, it sure feels as if it is. I can only speculate as to the reasons why people chose to return to being a paid employee. I’m sure the reasons are legit. But if you have that entrepreneurial spirit in you, the idea of giving up and going back to your previous life is depressing. Seriously depressing. That’s one way to tell if you’re cut out to be an entrepreneur. Everyone faces big challenges, especially during the startup phase. If you find yourself contemplating going back to your previous job when those challenges occur, and the idea doesn’t make you feel sick…maybe you should go back. 

#2 Don’t shame people for being employees

There’s a lot of noise on social media that seems to imply that staying in a paid job is for losers. I think we all know this is not true. Izzy also pointed out that for entrepreneurs to grow their companies they need employees. Good luck attracting people to work for you if you’re sending the message that entrepreneurs are superior. 


#3 Showing only the highlights is a disservice to potential entrepreneurs

One of the things I love about all the co-founders at Urban Misfit ventures is their willingness to share the reality of their entrepreneurial journey. Sure they celebrate successes. But honestly, you’ll see more Social Media content from these guys that talks about the struggles and lessons learned than their successes. I try and do the same. Admitting that we face challenges does not make us weak. It proves to people that we’re facing the same kinds of challenges other entrepreneurs face. By talking about how we’re working to overcome those challenges we can educate and inspire others. Don’t buy the image of the entrepreneur lying on the beach sipping Mais Tai’s while the passive revenue flows in. And if you’re looking for a slice of entrepreneurial reality check out Izzy and his three co-founders, Quentin Allums, Eric Didier, and Brema Brema.

#4 Entrepreneurship will humble you. 

Anyone who has started a business from scratch will recognize the truth in this statement. When we spoke Izzy shared that there have been times when the business did not have enough money to provide a paycheck to the founders. And like most early stage entrepreneurs this was often accompanied by the need to pay business expenses on their personal credit cards. I know that if I were to look back at the financial statements for the four businesses that I’ve started, I would find that on many occasions the largest accounts payable account was “Payable to Tim Alison.” This is a fancy way of identifying bills that I had to pay personally because the business did not have enough money in the bank.

Izzy also stressed the importance of staying humble when your business begins to get traction. He expressed personal admiration for his co-founder Quentin Allums who he insists is the same humble guy he met back in college. Quentin has been a guest on Screw the Naysayers, way back on Episode 24, we’ve spoken many times since, and this summer we’re going to meet face to face. I’m super pumped about that. I can attest to the point Izzy makes. The dude hasn’t changed. 

#5 It is possible to launch a startup without external funding 

How many times have you heard someone say “I’d like to start a business but I don’t have the money.” There seems to be this belief that to start and scale a business everyone must attract funding, either from the private sector or government loan programs. Not true, and in many ways bootstrapping the growth of your company is a great way of driving efficiencies into your decision making process. When you have money in the bank there is a tendency to spend it. I’m not saying that you can start and scale a business without spending any money. You can’t. But in most cases the amount of money is something you can raise on your own. If you’re afraid of investing that money that you don’t have clarity on what you want to do or you don’t believe that you can get the things you want in life. Those are the only two reasons why people settle. 

#6 You must ensure your employees understand your vision

Izzy stressed the importance of employees understanding the vision behind the company and the vision behind the founders. When your “employees believe in it, they will run through walls for you.” This is one of the things that I really enjoyed about running a small business. Even as the headcount increased I was always able to invest time with my employees. I made sure that they understood why the work we were doing was important. I helped them visualize why the work they were doing was important. When you do that you will have energized, loyal, and passionate employees. In my mind, if that’s not the case in a business, then the blame lies with the entrepreneur.   

# 7 It’s important to align yourself with the right people

Izzy brought this up on several occasions when we spoke. He talked about the importance, even early on, on being aware of the people you were giving access to you. This was not an elitist statement. Just an acknowledgement that the people you spend time with have a huge impact on your mindset. And they also share wisdom and stories that you can learn from. If you surround yourself with naysayers self doubt will inevitably creep into your mind. Naysayers are like viruses. To gain power they have to infect a host, and if you’re a business owner many naysayers will see you as the ideal host. This is not to say that you should only surround yourself with cheerleaders, folks that will tell you that you’re doing awesome, even if they don’t believe it or don’t have a clue how you’re doing. It’s nice to have people like that in your life. But you definitely need heart centred people that will offer observations and share experiences with you, even if it’s not what you want to hear. 

A last factoid about Izzy. Like Quentin Allums and myself Izzy will be on season 2 of Amazon Prime’s ‘The Social Movement” docuseries.

If you haven’t heard of my podcast yet, it’s a collection of real and raw stories from an eclectic mix of Thought Leaders, Entrepreneurs, WSJ and NYT Best Selling Authors, and a wide range of women and men who have overcome great adversity by finding the gift in their challenges. 

Check out the Screw the Naysayers Podcast anywhere you listen to podcasts or catch the Blog summaries here.  

Tim Alison

Tim Alison

Business Mentor, Harvard Speaker, Magnify You Facilitator, Author x 3, Podcast Host at Screw the Naysayers

Share on facebook
Share on twitter
Share on linkedin

Subscribe To Our Blog

Get inspiration, practical tips, and advice for living the life you want. All for FREE and delivered right to your inbox. Just enter your email below and join the community here at Screw The Naysayers.