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Optimistic Pessimism Leads to Starting 5 Companies With Gabe Galvez, CEO of CAPTARGET

“Not every idea needs to be huge. I have made a great life for myself hitting base hits. While we need industry-wide disrupters, there is nothing wrong with building simple, profitable mid-size businesses.”

I find the mind of the entrepreneur absolutely fascinating.

Gabe Galvez peaked my interest when I heard him as a guest on a recent podcast I listened to.

His approach to living his life and expecting total failure with every new deal he works provided a breath of fresh air which I believe every aspiring entrepreneur needs to hear.

Here are the highlights of our interview.

What is your elevator speech on your professional career: who are you, what have you done and how does that translate into value for your customers?

“I have built companies that have been acquired, acquired companies as a professional buyer and as a banker helped others exit their businesses. Some of these have been tremendous successes and some huge failures… welcome to a life of serial entrepreneurship.

My professional focus is pretty simple: generate profits. Having the freedom to pursue this mandate without too many restrictions is an incredible opportunity that allows me to be involved with a number of different companies at any given time.

Today I serve as the CEO of CAPTARGET, a private equity-focused deal organization and M&A back office service provider.”

Let’s show everyone you’re a normal human being. What’s your personality, hobbies, favorite places to visit, pet peeve? Tell us about YOU.

“I try to spend as much time outside as possible. I have been surfing for a good 25+ years but also enjoy diving, gardening, learning new things and spending time with my friends and family. I am a huge dog lover and bring my dog to work every day (along with just about everywhere else I go).

Over the last few years I have been spending more time in Mexico, where I could see myself living someday if I can ever slow down enough to make the move.

Having been so focused on my career for the last 15 years or so, I think most people would not believe that my real goal is to just enjoy doing much less than I do now. 

But won’t you be bored,” everyone seems to ask. My answer: I would sure like to find out before I am too old.”

What is something about you that most people don’t know that would surprise them?

“People may be surprised to know that I really dislike networking and find it very taxing to meet new people in general. Having spent much of my professional life in personality-forward roles, focusing on building deals or business development, the reality is I find these functions really taxing; the irony being that I am pretty good at both.

As such, in my personal life most of my friends are people I have known for decades. Maybe I am just really difficult, and these lifer friends are just more tolerant than most.”

What are two examples of how you consistently work outside of your comfort zone and how has that impacted your personal and professional growth?

“My perspective tends to lean towards ‘optimistic pessimist’. Because of this, I take a bit of a ‘why not’ approach to new projects, while always fully expecting total failure.

So, why do things that you believe at some level will fail?

Because once you understand that the failure doesn’t define you too deeply or hurt too much, you start enjoying the process regardless of the outcome.

Expecting and embracing the possibility of the worst has really freed me in a way that allows me to try new things, take risks and work outside of my comfort zone, maybe for no better reason than the result doesn’t really matter all that much, but the process of getting there can really be rewarding.”

Many people say success correlates with the people you meet in your life. Describe two that most impacted your success?

“For nearly the last decade I have been working with one primary business partner, Paul Saitowitz. Paul has helped me launch 5+ companies. While I might be an adequate executioner, I openly admit to not having many new ideas of my own. Most of our new business concepts, new product ideas and big important pivots were based on ideas Paul had. Knowing there is someone down the hall that is willing to work as hard as I am in uncertain circumstances empowers me greatly.”

Discuss one of the lowest points in your life personally or professionally and how it helped you get where you are today?

“I have never worked outside or for minimum wage, never had a problem with addiction, been broke but still had fun, and still talk to my family frequently, so I would like to think that my low points must have not been that low.

For me, my lowest times were less about events, and more about a lack of direction that lasted some years in my early twenties. I remember the maddening feeling of knowing how capable I was but not knowing how to apply that ability appropriately. I have always been very ambitious but have not until fairly recently known what to do with it.

This directionless motivation can be a heavy burden to bear that I believe few in my life understood. That terrible feeling has allowed me to get really passionate about finding meaning in work and life in general.”

What is the best lesson you learned from your worst boss?

“Let me first qualify this answer by saying, I have not had any really bad bosses. However, I did have one boss that made decisions so slowly – a classic paralysis by analysis guy. It felt impossible to move projects forward due to the road blocks of discussion, approval and investigation that I felt were not always warranted.

Now, taking a counter-cue to this boss, I always try to make decisions quickly, with the information I have on hand and resign myself to knowing that some of these will be wrong, but that pivoting quickly is not the worst thing that can happen.”

What are your “3 Lessons I Learned from My Most Memorable Failure”? 

  1. Everyone who has done anything of note has failed in a major way at some point. Give yourself permission to fail.
  2. Illuminating these failures is good for everyone. Talk about your failures!
  3. It only takes one big win to offset many more failures. You don’t have to have a perfect batting average to be a great player.

What unfiltered advice do you have for aspiring entrepreneurs or business owners looking to catch their big opportunity?

“This may sound too simplistic, but I have always encouraged young entrepreneurs to focus on businesses that have a quick path to profitability and/or businesses that do not require huge amounts of capital to validate.

Not every idea needs to be huge. I have made a great life for myself hitting base hits. While we need industry-wide disrupters, there is nothing wrong with building simple, profitable mid-size businesses.”

Looking back, what was the most non-conventional way you landed a memorable deal that made your success turn in the right direction?

“I got offered my first ‘real’ job while selling shoes in a mall. After interacting with a woman for several hours I learned that she recently started a company that needed help scaling. I didn’t know what I wanted to do with my life and she didn’t seem to have any better options than talking to me…. a match made in convenience!

After selling her on a bunch of shoes that I am sure she didn’t need she doubled back into the store and offered me a job on the spot. I remember, she said something like, ‘If you can deal with the type of person that tries shoes on for hours, you can deal with our customers’. That day, I think I doubled or tripled my income.”

What is your favorite podcast(s) you’re listening to currently and why?

Opt Out Life is really a great podcast. I love hearing stories about entrepreneurs who are building businesses specifically to support a better work life balance. It doesn’t hurt that I was recently on the podcast, too.” 🙂

What is one “efficiency hack” you use consistently in your life to keep your time and mind free to focus on your strengths and passions?

“If it’s not on my calendar I don’t give it mind share. This forces me to plan, often many days in advance and allows me to really unplug when the calendar permits. Some of my friends and family probably really find this annoying but if you want to hang out after work, or catch up on a long call, I even make them put the event in my calendar, so I can truly give them the time and attention they deserve when we are together. Be deliberate with how you allocate your time!”

What are you currently working on now? 

“I am trying to turn the corner on earlier stage projects and focus on ‘boring’ investments in operating companies and real estate.

Having just sold one of our companies, I am taking a bit more off time right now, but I am sure someone will talk me into something more dynamic sooner than later.”

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