Jeff Pruitt, CEO of Ethology and Tallwave, and general partner within Tallwave Capital, joins Justin Gray on this episode of “Driven: How Did I Get Here?” podcast. 

When you were growing up, did you know what you wanted to be?

My dad was in the construction business so he would take me to groundbreakings of buildings. I remember one of the new CEOs of Circle K talking about a turnaround they were doing. I was driving home with my dad, I was probably only 14, and I said to him, “That sounds interesting to me.” It was about being part of a company that might not be doing well and figuring out a way to turn it around. I turned that into being on the innovation side of things. 

What did you focus on when you were going to school?

I got sidetracked a bit. My dad said if you’re going to go in and try to run companies, get an accounting degree. That was the right advice, but I took that and turned it into go getting a job at Arthur Andersen. They probably were one of the more innovative accounting companies at the time, yet it wasn’t really who I was. So I was talking to a mentor partner at the time, and he introduced me to the founder of Microfin, who was really charismatic. He had a lot of big ideas on what he wanted to do in the marketplace, and it felt like the right time to jump out. I became the CFO, and ultimately the president.

Have you had mentors throughout your career? How important have those relationships been?

My dad imparted upon me some business things that sounded easy coming from someone who’s been through the trenches. Then you go and do it on your own and it’s never as easy. My mom was very attuned and connected with staying in the present. Those two things started to become the DNA that I was raised with. Now I’m part of a young presidents organization where you just get really good people around you. It helps to listen, to learn from their experiences and the obstacles they went through.

How do you find that balance when you’re trying to run an organization and are responsible for both the bottom line and the culture?

I’ve seen people who do it very, very well because they take the emotion out of it. You look at the team, you look at the accountability, and those who aren’t doing their job aren’t there any longer. I think that builds a culture of accountability. Whether it be your gen Xers or your millennials, people like to be held accountable.

I operate probably a little bit more on the emotional side of caring about what people think. Not specifically about me in general, but how they think about the company, and how they are growing as individuals in it. It’s the people that you bring around you that help foster and set that culture. It’s probably easier said than done and I’m learning this as I go.

What was the key to trying to be involved in multiple ventures at once?

I am a believer that advice going into these companies needs to be not just financial advice, but a network of being able to make action happen when you’re engaged with them.

What has been the biggest challenge along your journey?

I think the challenges of any CEO center around the people management side. Not from a negative perspective, but you’ve got to have fun doing it. It’s fun to meet people and try to discover what makes them great. Then figure out the ways you can make them great while making the company great.

You’ve got to think of all stakeholders or shareholders, and that’s your employees and your investors and clients. Those things have to be aligned to make it as seamless as possible because it’s a lot of work it those things are not aligned.

How you identify talent through an interview question?

I try to get down to what inspires them. What gets them to tick? What makes them feel successful as individuals? The hobby question tends to bring out the passion. You can get a lot about somebody and what kind of role they would be great in by finding out what they like to do personally.

What’s one piece of advice you’d share?

I would say do one thing at a time. Nail it, and then sustain it operational-wise, and then build it from there. 

Connect with Jeff Pruit on Twitter at @jeffreypruitt, or visit Tallwave.com and Ethology.com.

Sangram Vajrem, author #ABM, co-founder and CMO at Terminus, founder #FlipMyFunnel, joins host Justin Gray, founder and CEO of LeadMD in this episode of Driven: How’d I Get Here?

What did you want to be when you grew up? 

I always wanted to be - and at some point I might be actually - a pilot. I always wanted to see the world from a completely different perspective, and I don’t think there is a better perspective than being up in the sky looking down and seeing the world in a different way. None of us get a chance to do that often. At some point I do want to get a mini pilot’s license and just fly around Georgia or something so I can see the lands that I live on. 

You have a bachelor’s from Nagpur University in India and a master’s from the University of Alabama, both in computer science, what were you hoping to do with that degree?

I wanted to get my masters and that was the easiest way to get it because I did my bachelor’s in computer science. If I wanted to do anything else, there’s no way I would’ve gotten assistance. So to me that was one step in that direction. I really wanted to explore the States, and I didn’t really think too much about it outside of ‘It would be cool to have a master’s degree. People would regard me, that I’ve gotten a little education under my belt.’ It wasn’t to become a computer science or work at NASA or anything like that. It was simply a means to get here [to the US] and be part of the process, and really explore it and understand, and see why my brother was so excited about the idea of me being here.

I know you as a marketer, and a business owner, so where does that come into this equation?

I was with Deloitte for a couple of years, then I was with a company in Atlanta. I got married during that time and my wife didn’t want me to travel as much so with a couple of buddies of mine, we began thinking about doing something together. For three years we ran a startup, while I was doing all these other jobs, but it went nowhere. We had no customers. We didn’t do anything, but in that process I learned about marketing a company, building a product, and what it takes. All three of us were doing something else, and I learned a very valuable lesson. That you can’t really do a startup half-heartedly. You have to put your heart and soul, everything into it for it to even have a heartbeat.

Those three years were really when I realized, wait a minute, I can add value in all of these areas. Marketing was an area that I really took an interest to, because I love storytelling, I love the idea of understanding what happens and how people emotionally react to stuff. I think that part really drove me into marketing. Those three years are what I consider my best three years of learning, because I learned more on that job than anything else I was doing.

How did you decide to go from a massive organization on a global scale to starting a startup business?

I’ve always gone against the flow, and going back through a little bit of history, this was the time for me to make a decision. At that point we had our second baby. My wife had quit her job because I was working for Salesforce, getting paid really well. I had a moment, I don’t know if it happens to everyone or if it happens more than once to anyone, to have this moment of clarity. To know that you can see something happen in front of you, even though it hasn’t happened at all, and you just have this feeling in your gut. That ‘Oh man, I can touch it. I can feel this thing even though I’ve never done this, how the hell am I going to do it?’ You just have this amazing pull, like a magnetic pull towards something, and that’s what I really felt. It was definitely a spiritual thing for me.

So I went back and told my wife that I really think I should do this thing. We’re not going to have much money for the next few years. We would living paycheck to paycheck, but I really have this feeling that this is going to work. She took a week to think about it then said something to me that is really why I have been so driven in the last year. She said look, this is very unconventional, and you are a first-generation immigrant here. I am a first-generation immigrant. This is all crazy and insane, but if you are so driven, I am going to give you one year. Within one year, you have to prove that this thing has real legs, and if it doesn’t, then you have to go find a real job. So I said deal. 

So for one year I had to hustle. Driving 100 percent and trying to only get through one year and trying to prove that I could do it. Since she put a condition on it like that, it made me do things that I don’t think I would’ve done otherwise. I think I owe it to my wife to even have the amount of success that we have as a company today. 

Takeaway quote: Push yourself to think as big as you possibly can, then come back to it and see what you can really achieve. I think those two processes are extremely important to do anything beyond a standard level.

Connect with Sangram at:

@SangramVajre on Twitter or Google SangramVajre

Dean Heckler, founder and lead designer at Heckler Design, joins host Justin Gray in this episode of Driven: How Did I Get Here? Dean explains what drove him to shutter his software development company to pursue a passion in industrial design.

What did you want to be when you grew up?

From the earliest I can remember my dad always brought computers home. We had some of the earliest computers. So I was just spoiled with computers early on and I think that influenced my decision to stick close to technology. At some point in high school I thought architecture would be a good career path, but I heard a lot of horror stories from folks a few years ahead of me. So majored in business and graduated with a couple business degrees right in the middle of the dot-com boom so I was thrust right back into technology 

I worked for a software company out of college doing early virtual reality. 

How did you get that position?

I knew someone there, and that person knew that I was savvy in technology and graduating with a management degree, and thought I could manage a growing team of developers. So I did that for a year and a half while doing some work on the side – digital documentation and consulting. Ultimately I ended up starting my own software company and ran that for eight years, helping out industrial facilities digitize their documentation. 

What led to Heckler Design? Was it a major pivot or just other interests that inspired you to launch it?

Over the course of the 8-year software business, in my spare time, I would sketch designs for furniture…I just had my own ideas for furniture. A lot of furniture in my home I drew up and when I had extra money, had somebody make it. 

When did you find success with it?

I remember thinking if it’s going to cost that much to make one [desk], how much is it going to cost to make 10? If I want one of these things maybe the better idea is to make 10 or 20 of them and try to sell the other ones off to get the unit cost down, and to maybe make some money. That’s essentially what happened. I made a prototype, it was bad. Made another prototype, it was better. That was late 2007 and in January 2008, I put up a website and I notified a couple design blogs. That was the night before Mac World, in which Steve Jobs introduced the MacBook Air for the first time. It might have been a little bit of intention to get the news out about the desk before Mac World. 

Where is Heckler Design now?

Heckler Design is up to 12 employees, and we have a network of vendors throughout Phoenix. How we got from a desk to where we are today was again heavily impacted by Apple. Steve Jobs introduced the iPad and I remember watching the introduction thinking this is going to be a powerful business tool. I knew every accessory maker in the world was going to bring out a plastic iPad stand. I make products out of heavy steel, and I think this iPad thing is going to be used in business, so let’s see if I can make a commercial grade iPad stand.

That turned out to be our @Rest product, and since it was commercial grade it got picked up by a few of the early companies that made commercial applications for the iPad. We sold @Rest to small business owners who were just starting to use iPads in their business. The feedback was ‘This is great, but could you do a secure version?’

That’s when we designed the WindFall Stand, which is now our main product line.  

I think one of the key takeaways here is know what you want to do. Which is so important, yet so difficult to find these days.

It’s a great theme of this entire podcast, which is I did run a software company. It was fun, but something was missing. When I finally got to do physical product I realized that was what I loved to do. So it’s really about maintaining my ability to have a creative platform. To come up with new ideas. To make other physical products, and put them out there in the world. Weather we create and ship a million units or five hundred units, I don’t really care. As long as it is still a very functional, profitable business, and still a platform to put out good things.

Take Away Quote:  Find something that you love, such as a hobby, and figure out a way to make it into a business.

In this episode, host Justin Gray, CEO and founder of LeadMD, talks to Brian Provost VP of digital strategy at Define Media Group, about how he accidentally stumbled upon his first business and parlayed that into the success he has achieved today.

What did you want to be when you grew up?

I wanted to be a lot of things. There was a period where I wanted to be an attorney, a race car driver, a Green Beret...

You graduated from Texas A&M, what was your major?

I had a double major in finance and accounting. I always kind of felt that there was this entrepreneurial or business focus that I’ve always been interested in, and those just felt like the best way to learn the inner workings of how business actually works.

Were there any main influences at the college level that drove you in a certain direction?

Texas A&M had one of the more impressive early internet labs. Much to my GPA’s chagrin, I would spend a lot of time just screwing around in the internet lab.

What happened after you graduated?

My first business was a motorsports venture where we tried to create the ‘US Open’ of motorsports. It was just more playing than it was a real business, but it was a real business in the sense that I had to learn all the day-to-day stuff. It was more of a lab for me if nothing else.

A lot of us were big parts of other online motorsports communities, so we coalesced this universe of well-known influencers within the car community, and put together this event. That experience taught me a lot about community building on the web and even things like housing the data from all the races. I kept building to this point where between that and teaching track clubs on the weekend, I created a massive rolodex. I didn’t know it at the time, but I had all these really cool contacts in the industry that I knew on a personal level. 

So after the motorsports business when I tried to formalize an internet offering and consulting company I walked into a business right away at the highest level. I don’t think I was really prepared to be walking into boardrooms at the Fortune 500 level at that time. I was a mid-20s guy and was just used to hanging out with these guys.

What advice would you give to your younger self?

I would have told myself to become a little bit more technical a little bit quicker. We’ve got the Weather Channel which is in 60 plus countries and each country has millions of pages. I quickly have to shift from the 50,000-foot strategic guy to working with the devs and figuring out technical issues. To be more of a proficient technical marketer, I think that would have made me a stronger asset to not only my team but to my career.

What do you find provides the best insight when you are interviewing new candidates?

It took us over four years to find our latest hire. We protect this business so much from a lifestyle perspective. We’re always trying to find the human level stuff? Like, how is this person going to fit in a team? As people will tell you they tend to hire IQ and DNA over expertise because expertise is going to be invalidated in a year or two. So hire really strong utility infielders and expect them to rise to the occasion.

Take away quote: Each turn in life is another opportunity to form a relationship that’s probably going to pay off down the road, so don’t skip out.

In this episode of the “How Did I Get Here?” podcast, host Justin Gray talks with Heidi Jannenga, co-founder and president of WebPT, about making big transitions and trusting in the path.

Did you know what you wanted to be when you grew up?

Well, interesting. Going back to my childhood, I actually wanted to be a veterinarian. So in some capacity, I knew I had this need to help people, or help things. In this case, animals. So I guess even from an early age I recognized that innate piece of who I am, at the core of really wanting to be there to help others. Fast forward into what I actually became as my career as a physical therapist.

Let’s fast forward to the point where you become co-founder of a software startup?

What as the impetus for that change? I had been practicing for 15 years and had kind of reached the top of my game in terms of treating athletes of all sorts. I was running three clinics in the greater Phoenix area and had P&L responsibilities. During that time, I realized one of our biggest expenses was transcription and dictation. I just so happened to be dating a software engineer and entrepreneur at the time, and so not having a lot of technology sense at the time, I asked if he could help me find EMR software for physical therapists. Needless to say, nothing existed. So we started off on this journey together, of trying to put the brain and workflow of a physical therapist into a software program. It took us about nine months to get that first v1 prototype working.

What was the biggest challenge along the way? What did you guys have to overcome in growing that initial idea into the business that it is today?

Going from being a physical therapist and clinic director transitioning into software development…talk about polar opposites. That was pretty difficult for me. As we bootstrapped through those first four years, I continued to work full time at the clinic. I stepped down as clinic director a year in for two reasons. The business was starting to grow, but I also got pregnant. So trying to juggle three full-time things at once was just, was just not something I wanted to continue to do.

What do you look for in the employees you hire today to try to keep that spirit in the business going?

As we started building the business, something that really was a conscious effort for us was to build a culture that we thought was going to be sustainable and scalable. We’ve always hired for culture first over skill set, and we still do that today. We have a culture that is very collaborative and open. It’s hardworking but it’s still fun. We look for people who really want to give 100 percent to what they’re doing. We use a lot of experiential and sometimes off-the-wall questions trying to peel back who that person is at the core and not just that superficial interview persona that comes to every interview.

Do you have a favorite interview question?

I have a couple. One for me, since we’re in Arizona, I like to bring in the Native American culture, and in the Native American culture everyone has a spirit animal. We ask people what their spirit animal is and why – explaining that the spirit animal is your persona embodied in an animal. It always takes people aback a little bit.

Douglas Karr joins host Justin Gray in episode 4 of the “How Did I Get Here? podcast. Doug is the CEO of DK New Media and co-founder and CMO of CircuPress, an email service provider. He has grown to become an established leader in the marketing technology space and is a serial entrepreneur.

What did you want to be when you grew up?

For a long time, I think I wanted to be an architect of all things. I loved drafting and drawing. I don’t think I had a schoolbook that didn’t have some sort of creature or building in it.  Where did that lead you? Did you go to school for architecture? No, that’s the weird thing. When I went through high school, I was always getting in trouble, and partying way too hard, and reckless. I wound up messing up my chances of ever going to college. I graduated high school, and I went straight into the US Navy. 

After you’re done with the Navy, where do you go at that point?

In the Navy, I was an electrician, and after I got out, the workforce was pretty tough back then so I bounced around. I delivered pizzas for Pizza Hut – I did whatever I could do for money – changed peoples’ brakes, worked at the shipyard for a couple years. Then a job opening came up to work at the local newspaper as an industrial electrician. That was really my first dive into media.

We were switching all of our equipment over to internet based, we reinstalled fiber and started networking all of the equipment. We started to do predictive maintenance on the equipment based on failure rates and monitoring productivity over time. That’s when we saw the opportunity for database marketing and I started to make the shift from monitoring and troubleshooting databases and equipment to monitoring and troubleshooting marketing. 

What was the big catalyst to move from a database marketing manager to what you’re doing right now? How did you come to own your own business? 

The catalyst was easy, I got fired. So that puts you on a different road. I was really frustrated when I was working in the newspaper industry and the slow adoption of digital. I knew the future was absolutely in digital marketing. I had a string of incredible successes. I worked for the Indianapolis Colts during the year that they won the Super Bowl. We implemented Exact Target, and Exact Target figured out that I was doing stuff with their system that they hadn’t done yet. They offered me a job.

I then went on to co-found Compendium, which eventually sold to Oracle. It was at Compendium that I really started to see the light that you know what, I think it’s time for me to start doing my own thing. What we saw in the industry at the time were marketing agencies that were specializing. I wanted to start my own agency that was more cross channel to help marketers kind of dial in and connect the dots. I started DK New Media seven years ago, and it’s been a great road ever since.

What led to the confidence to go out and do that? Was there a big influence that led to that?

You know there really was and it was probably during that string of successes that all of a sudden, I’m sitting in all these board rooms and I’m figuring out that these people are paying attention to me and they respect the decisions that I’m making. I start to wonder why I’m not sitting in a board room all the time. It took me doing that for a while before I started opening my eyes that, “hey, why aren’t you leading a company, and why aren’t you driving this change?”.

What advice would you give to your younger self?

You do what you have to do to pay the bills. It may not be what you’re passionate about, but you can find things to get passionate about and you can find opportunities along the way. If you just keep driving, you’ll eventually see those opportunities. If you don’t take any, you’re missing the boat.

Do you think you could hire someone else to do your job? If so, what would those traits be if you had to hire someone to replace yourself?

One of the biggest things is to know what you’re good at and what you’re bad at. Sitting across the room from me right now is my business partner. She is everything that I’m not. I made it a point to not hire someone like myself. One of the key things that you’ll find with any entrepreneur is they recognize their weaknesses, and they play to their strengths. They hire people who can make up the difference or partner with people who can do those other things.

As you are staffing your organizations, what is your favorite interview question that you feel really gets to the heart of who someone is?

I never read resumes. I go straight to online, and straight to portfolios, and Facebook pages, and everything else. I often ask people what they love to do on the side. You’ll find people with some kind of creative outlet, whether it’s music or gaming. When they have these creative outlets, I think they have really good balance.

Takeaway quote: What I figured out eventually was leadership was one of the components that everybody has.

Kathy Sacks, founder, investor, consultant, joins Justin Gray on this episode of the “How Did I Get Here” podcast. Kathy currently runs advisory firm Coleap where she advises founders and executives in growth strategies and marketing. Kathy also invests in early-stage tech startups.

Growing up, did you have a clear vision on what you were going to be?

Well at one point, as a child of the 80s, I did want to be a solid gold dancer at one point. And thank God I didn’t follow that path. But for a hot minute there. I grew up in New Jersey and I grew up with immigrant parents. My parents both escaped communist Hungary in the 60s. So I got a hard work ethic at an early age. But looking back, I wanted to be many things, and I’m still figuring that out today. I mean aren’t you? Did you really figure that out?

I think the path of reinvention, especially today, happens often in one's career. And I think it is really healthy.

What was the first job post college or first real job? 

I wanted to work in New York City and to be a buyer at Macy’s. So I went to school in the city and after that ended up getting an entry level job at a company call Domestications – it was a catalog.  $19,000 was my salary and my job was to fax orders to the different suppliers that were buying items from this catalog.

So let’s fast forward to today, you’ve had huge amount of success. You’re out on your own, running your own company, as well as investing in a ton of early stage organizations. What made you say, “I want to be an entrepreneur”?

Well I grew up with one. I saw the seasonality and stress of it, but also respected and admired the sense of freedom.  So I always knew there would be entrepreneurship in my future and I don’t like people telling me what to do necessarily.

Is there any advice you would give to your younger self looking back over all these experiences that you’ve had?

The advice would be to not take myself so seriously for sure. When I look back, I’d say that I just needed to chill out a little. Continue to work hard, but be more open and willing to fail.

If you could hire anyone to do what you’re doing today, what type of person and traits would you look for?

When you are building a team, you don’t just want to hire a bunch of clones of yourself because you just get a bunch of stuff that isn’t going to lead to high performing teams. You get groupthink, and you get sameness. Today, a lot of what I do is with founders, CEOs and their teams around how to grow. And the area of growth I’m most focused on is business strategy and customer acquisition. Within that, the sauce that I think is really the most important, but not necessarily its own department when you’re an early stage company is the people, and specific to people, it’s leadership. So I’m really interested in the intersection of business strategy, growth, and leadership. And how you develop yourself as a leader so you can multiply your people, and build a high performing team that ends up building a really great company.

Take away quote: “Spread your wings. Try things that you might not be sure if you’re any good at, but if you have that curiosity, try it.”

For Kathy’s blog posts about business strategy, check out kathysacks.com.

In this episode, serial entrepreneur Pat Sullivan, CEO of Ryver and self-described paradox, talks with host Justin Gray about his eventual path to entrepreneurship and the traits he believes forms a great entrepreneur.

Did you know you wanted to be an entrepreneur when you grew up?

When I was growing up I could not spell entrepreneur, and it never occurred to me that I would be an entrepreneur. In fact, I thought about that question a lot. What do I want to be when I grow up? And I have no recollection of wanting to be anything.  

What was your first job then?

My first job was selling printing in Chicago, and I did that for about 10 years or so.

What caused you to make a shift, and at that point create a software?

After the job selling printing, I went to work for 3M, and that was my introduction into the technology world. Soon thereafter, I worked for a microcomputer dealer, and during that time I taught myself how to program because I became obsessed with the idea of automating everything I did as a salesman. And the last thing that I built was a contact management module and little did I know that basically I was building a prototype for what ultimately became ACT. 

So you’re in sales you decide to teach yourself programing and you basically produce an MVP and go to market 10 months later. During that time, was there a mentor or huge influence on your ability to say “I can go out there and do this?” 

Well I have thought a lot about that in the past and I have said that probably the biggest impact on my life came from my father and probably my mother as well. I tell people that the greatest gift they gave me was that I could do anything that I set my mind to. 

Has there been one major or is there a struggle that stands out in your mind along the way - a time where you were like “I don’t know if I can do this?”

I can’t site a single one. I would say there were hundreds. Running a startup is very hard. You are going to run into things that you did not expect. You are going to make mistakes. You are going to go down paths that prove to be a dead end. And it is the tenacity that is required to say OK, there is an answer to this. I made a mistake. What can I learn from it, what does this teach me and where do I go from here? And you know being driven by the belief that there is always an answer.

What advice would you give to your younger self?

I would advise myself, and anyone else, to act on your instincts.

How do you find good employees?  What is your favorite interview questions when you are trying to get to the heart of will this person be someone I want to take on this journey with me?

I don’t have a specific question, it’s more of a conversation. I’m really looking for social intelligence as much as I am looking for technical intelligence. Do I like this person? Can I work with this person?

Who would you hire to do your job? What would be the traits of that individual?

Tenacity. I personally believe, based on things I’ve read, is that the best entrepreneurs tend to be generalists. They have lots of interests. It would have to be someone who is willing to do something that others might not do.

Take away quote: I tell entrepreneurs now you know if you want to know if your a leader, turn around and see if anybody’s following you. 

In this inaugural episode, Craig Rosenberg, co-founder and chief analyst at TOPO, switches roles with host Justin Gray, CEO of LeadMD. Craig goes in depth with Justin about his journey and how he came to be a serial entrepreneur and now host of the “How Did I Get Here?” podcast.

Meet Justin Gray

What is your role?

To answer that question succinctly, I am the CEO of LeadMD, but my role is a little more difficult to define because I really do any of the shit that anyone else doesn’t want to do, or can’t do.

What did you want to be when you grew up?

I wanted to be a journalism major for the purpose of becoming a writer.

Along the way, as you got to where you are today, what advice did you receive on how to get there?

The sound advice I got across the board was that there was a very traditional, structured path to success in some regard or another.

What was your major in college?

It was journalism for the first two years, then switched to business with a specialty in marketing.

Who or what has been the biggest influence on your career?

There’s obviously a ton of people that have been influential, but I think the biggest influence for me was becoming part of a startup when I was 26.

What advice would you give to your younger self?

I would honestly not go to work directly. I would say, take some time and try to experience some other things.

Take away quote: "I became disenfranchised with a normal path and started to take interesting approaches to creating my own business."