April 30, 2024

Episode #139: Steve Iskander – Intrepid Finance

Steve Iskander, the dynamic founder of Intrepid Finance, has redefined the landscape of nationwide financing. Leading Intrepid, a subsidiary of Masik Management Group, Steve focuses on providing seamless, non-dilutive growth capital to diverse businesses. He’s dedicated to making capital access simple and swift, fueling accelerated growth for enterprises at various stages.

Beyond Intrepid, Steve heads Masik Management Group, offering his expertise to companies navigating growth challenges.

With over 15 years in the equipment finance industry, Steve has managed a portfolio of over $500 million and contributed to a Berkshire Hathaway-owned leasing company. His entrepreneurial ventures, including DriverReach and ParcelInsights, showcase his innovative spirit, including ParcelInsights’ acquisition in 2021 by a New York-based equity firm highlights his strategic acumen.

A recognized industry voice, Steve has been featured in prominent publications like Inc Magazine, FleetOwner Magazine, and the Indiana Business Journal. He holds degrees from Indiana University Bloomington, Masters degrees from Ball State University and actively contributes to Ball State’s MBA Advisory Board.

Steve’s strength lies in driving growth, crafting long-term strategies, and enhancing operational efficiency, particularly in the supply chain and logistics sectors. He believes in the transformative power of effective leadership and strategic tools for business growth.

Outside of his professional life, Steve is a dedicated family man and an avid triathlete, having completed numerous IRONMAN races. His endurance in sports mirrors the resilience and determination he brings to his professional pursuits.

In honor of the fellow business owners in your life that had an impact on you becoming the person you are today, let’s celebrate them. Click this link to apply to be on our podcast to recognize those people: https://www.BeMADTogether.com


Intro: You’re listening to the Self Made is a Myth, Make a Difference Together show with your host coach Tim Campsall, where we talk with successful business owners to hear the stories of their journeys in building their successful businesses. And more importantly, we recognize the folks who helped them excel because we know that achieving business success is not something we can do on our own.

Coach Tim Campsall: Hello everyone. This is coach Tim Campsall, and I’m excited to have a fellow business owner from Indiana with us today. Something new. So what’s so unique about my guest is he’s an avid triathlete and has completed numerous Ironmans. We’re going to ask him about that because that is intense. In his downtime he enjoys sitting and daydreaming about topics and challenges as well as just, relaxing and taking it all in.

And he’s most proud of the company that he’s built along with the amazing team that he has. And it is my pleasure to welcome Steve to the show today. Hello, Steve.

Steve Iskander: Hey, Tim. Thanks for having me on, man. You speak so highly of me. That’s amazing. Sounds much better than I really am.

Coach Tim Campsall: Hey, let’s have you introduce yourself.

Tell us your full name and a little bit about of your personal story, like where you were born and live and about your family and hobbies.

Steve Iskander: Yeah, no, absolutely. Again, thanks for having me on. So again, Steve Iskander, I own Intrepid Finance and grew up just north of Indianapolis in a town called Logan Sport.

We’ll probably come back to that at some point as a lot of my business experience from childhood came from Logan Sport. Just grew up in Logan Sport, and later moved to Marion. Went on to college, did my undergrad at IU, and then my grad and master’s degree at Butler and Ball State. And in that time, working for a couple of companies along the way, really cut my teeth into the business world, and had the opportunity to land at a Berkshire Hathaway owned company right out of college that really cut my teeth in the industry as a whole and provided me with a ton of experience.

Coach Tim Campsall: Fantastic. And how about on the personal side? You’re a triathlete. Tell us a little bit. How’d you get into that?

Steve Iskander: Yeah. Very random. Never really set out to do triathlons, let alone an Ironman in life. But as I started realizing that I perform better as a business owner, as just an employee, By finding other activities to do that were relaxing and for me running is relaxing. A lot of people can’t say that. It is it is enjoyable to me and I get the best thinking and strategy done out there.

So I realized that I had a lot of endurance and I think it takes that in business and in triathlon obviously, so I would run and run and friends would tell me well jump on a bike and see how long you can bike after you run forever, and I’d do that and then they’d just one day Tim some guy was like hey, dude, you’re doing like an iron man.

I’m like you know what I really am. And for me, I was actually just doing it to motivate myself to stay positive, a mental mindset, a relaxation, as well as it almost forces you hours of nothing, but thinking by yourself to go out on a bike or a long ride, run through the country.

When you think of lots of strategic things that you’re no longer in that day to day group thing.

So the evolution, I use triathlon to really help relax me from working on my business. I really found that it helped me help motivate me and give me drive and additional clarity within.

Coach Tim Campsall: That’s fantastic. And so you, you’ve said numerous, what’s been your favorite Ironman that you’ve participated in?

Steve Iskander: Favorite. You always remember your first one, 40. 6. So I’ve done 24 Ironman’s. 21 70. 6, including I’ve got one coming up in about two weeks that I’ll fly down to Florida and I’ll do that one. But Chad, the guy I did my first 140. 6 mile triathlon, is always near, near and dear to my heart.

So Only a hundred and some miles.

Steve Iskander: 140 miles. You get a lot of thinking done out there. Tim, you look at a lot of the statistics and a ton of Ironman athletes went male or female are previous salespeople, CEOs, founders of companies, and So they’re so intertwined on just endurance and discipline and I call it mental scarring. Being able to get punched in the face and keep going. The mental scarring of it as well, so if i’m not doing triathlon, I say i’m fishing I think I might have told you before I like to sit out and go fishing sometimes with no bait on my fish hook.

Coach Tim Campsall: Yeah,

Steve Iskander: So I just sit there and look at the retention pond.

Everybody thinks I’m crazy If I sit there and have a fishing pole in my hand i’m just Sitting there fishing. So you’re catching me out there doing a lot of my strategic planning next to the retention pond with a fishing pool in the water, but no bait.

Coach Tim Campsall: Steve. What’s a funny story that your family likes to tell about you that you’d be willing to share with us?

Steve Iskander: Oh man. Yeah. The willing to share is always, yeah, I’ve got three older brothers, so God knows what they would say. Nothing appropriate for this, I think of when I was a kid and it’s almost business related. I was probably 10, 12, maybe 13 years old. And right where you’re graduating from the kid’s menu to the adult menu portion sizes.

And I remember going out to dinner with my dad, which had a positive impact on my life. But I remember sitting there talking to my dad, trying to negotiate that I would eat off the kid’s menu. Instead of the more expensive adult menu, we would split the difference in the cost And he would keep three dollars and we both win. I think that was like the early childhood negotiation and childhood story I think it was in Steve’s DNA, 10 years old, he’s trying to negotiate on what he eats for dinner and tries to hit the parents up for money.

But needless to say, that did not work. I’m just fortunate that I got food on the table that day. He didn’t make me pay all of it.

Coach Tim Campsall: Hey, tell us how did your business come about and at what point did you have the confidence that you could run your own business?

Steve Iskander: Yeah. So Intrepid has been an evolution of multiple companies that I’ve either owned or been a part of to help scale up.

And really I was looking at Intrepid what spun off Intrepid is that in a former life, I was raising capital from a small business. We were very legitimate, small business. We were up and coming, we were doing well, we were growing, but the land opportunities, everybody calls America. There wasn’t any money for small businesses.

It’s so much more difficult than what people think that run a small business. If it’s a one man band or a, 5, 000 person company. And when I realized what I kept running into, I couldn’t scale because they didn’t have the capital because much of the capital in the market is rear view mirror looking.

They want to see what you’ve already done.

Coach Tim Campsall: Yep.

Steve Iskander: That doesn’t really help you in the future. If you’re always looking out the rear view mirror. So I started looking at it saying, Hey, there has to be in a way for early stage founders to get access to growth capital. Including without dilution because what we were seeing, and I was talking to my friends out there or guys were just taking stupid money as they call it. They really wanted money, but they say they needed vc because they needed a partner what they really meant is I needed an atm machine That is about 10 partners 90 atm You know It was so hard to get money Tim. I did the normal like most small businesses do I walked around town. I tapped hands across desk. I did my presentation.

I smiled. I did all the whining and dining I had a legit business, but people really weren’t super interested in it and said, Hey, there has to be a different way, especially in the technology industry. There has to be a better way of being able to provide companies for, with growth capital. And hence Intrepid was born.

What started out as literally a hobby. With no intent to scale this. It was just going to be me then had a couple of people that are like, Hey, I’ll jump on for the ride for fun and see where it goes too. And it’s been quite the journey and expansion. I would have never imagined it would be this large already.

Coach Tim Campsall: So Steve, tell us a little bit more about the company. Say the name again, what do you guys do? How do you help people?

Steve Iskander: Yeah. So again, Intrepid Finance. So we are a revenue-based financer, and then we have a technology piece of the company as well. So we go in and provide companies with early stage growth capital.

And I say early stage, but really growth capital. We’re not providing loans. We’re not providing four or five year amortization schedules. We’re really providing companies growth capital that have a plan. Exactly how they’re going to do it. I always say it’s called drag, right? They exactly understand their projections.

They click and excel and they drag right. And this is what’s going to happen based on growth and churn. They have a true plan. And not I say a VC cash burn, just keep throwing more money at it and figuring it out. So a lot of what we’re going to provide is going to be bridging Mez debt. But we also have a technology solution that instantaneously provides companies with essentially a marketplace that allows them to see what their debt options are.

So within seconds, a company can complete an application. They can connect their bank account to 16, 000 financial institutions. They can connect all the major accounting systems in seconds. Our our technology will run essentially analysis on it. See if they’re eligible to be written in house by us and our team provide the growth capital.

And if not, it’ll match them with another private non depository lender somewhere in the United States that will take that deal based on a lot of attributes for everything from the industry that forbidden the growth, the term, the EBITDA, the negative EBITDA, the ownership, the green card, the minority.

And it sorts all of that algorithm and we’ve got it down to around a 98 percent science that we can get it into a provider that will take that deal by exactly what the information you provided on. And that’s what I believe is really important for a small business owner is no longer having to beg for grandma to give you money, dancing across the VCs desk or selling equity at crazy dilution rates.

Trying to put it on your credit card, which is just not scalable as a solution to say, Hey, someone out there loves your business and loves your ratios, exactly how they are in your story. Why don’t I just partner you with them? Because they are a private funder that provides growth capital to growth coaches, for instance, that are located in the Midwest and they like it and they like the size of your company.

So that’s a lot of what we do. And then we white label the entire technology to call what I call a bank in a box that allows anybody to have revenue as a service and be able to provide any of their clients financing nationwide. From a white label technology solution running through our conduit and our a hundred plus private lenders.

Coach Tim Campsall: Fantastic. I have a client I need to introduce you to offline. So let’s let’s talk about that afterwards. Steve, share a story where someone pushed you or inspired you that you could do it and the impact that person had on you.

Steve Iskander: The story is someone that pushed me or impact me. That’s a good one, there’s a ton of people that impact me.

I feel like I have an impact and something positive every day that I’m getting impact being impacted on, a story.

Coach Tim Campsall: Maybe a situation where you didn’t, you weren’t sure that you could do it or you didn’t know how to do it. And, somebody came alongside you and inspired you or gave you a little nudge and said, Hey, Steve, here’s you’ve got this.

Steve Iskander: Yeah, I think it’s one of the guys that I look up to. It’s also on my board. Andrew. He’s actually here and in Indianapolis as well and as I sometimes tell himor usually tell him my crazy ideas on doing it and he really helped me I say from the Ben Franklin t diagram, a graph and say what are the pros and cons of it?

But really outweighing understanding what is the absolute worst case I lose money. I gotta go find another job Am I really scared because of narcissism and ego and social media? Or do I really truly see a path there? And I think he helped really filter that out for me on why I was maybe more reluctant to try.

Coach Tim Campsall: Yeah, I love it. That, that fear can be a big barrier, right? We actually define fear as false expectations appearing real.

Steve Iskander: 100%.

Coach Tim Campsall: So what you just said what’s the worst case scenario? What’s the best case scenario? Usually, we’re assuming the worst case and that, Paralyzes us for making a decision.

So being able to break it down and go, Oh yeah, but here’s the flip side of that. Here’s the best case scenario. Here’s the most probable. And now let’s move forward at the most probable.

Steve Iskander: And that’s, what’s helped me along the way. Andrew has been a positive influence for, almost a dozen years now on, on this and also triathlete triathlon partner of mine, I trained with and talked through a lot of that and even my previous company.

And I always go back, I think a lot through quotes. And I think of this Tony Robbins quote that I saw one day, and it said, don’t think about all the things that could go wrong. Think about all the things that could go right. And it stuck with me, Tim. And. And that stuck with me so much. It was that day that I made the decision to go launch my company parcel insights.

I’m finally swallowed it down and said, I’m going to launch parcel insights, my previous company. I launched that company later exiting to another firm here in town and private equity on a very successful exit. Nice. And it was just that perfect timing of understanding, what does scare me about failing as an owner?

It’s not the money. It, a lot of it is just the mental side of the failure side of it. So can I get past that? Can I think clearly? Do I have a clear plan on it? And again, going back to triathlon and fishing, that’s where a lot of, I put my thinking to put this together and Get out of the half empty glass.

I love that.

Coach Tim Campsall: So what’s been the biggest learning then as a business owner?

Steve Iskander: The biggest, I feel like I should write a book, but I feel like most of us, this owner should write a book. I have everything not to do. I could probably write well on that. Again, staying in the quote phase, Mike Tyson says, everybody has a plan until they get punched in the face, And that holds so true with small businesses, projections, financials, people, business, marketing, everything you think.

And I think the one thing is it, nothing’s going to go to the plan. You just have to accept it’s not going to go to the plan. Am I agile, fast enough, smart enough? Do I have the right people surrounding me and right advisors to myself to help navigate what path I’m going to go down? And I think that’s, Probably the biggest lesson is you’re not the expert, you are, I seen it one of the guys last night, I said I gotten pretty good at pulling genies out of bottles and, being quite the wizard on things, but that’s not my choice.

Coach Tim Campsall: Yeah.

Steve Iskander: You learn that from being a small business owner. So I think that’s probably the biggest biggest in right after that, everything takes longer.

Coach Tim Campsall: Yeah.

Steve Iskander: It doesn’t matter if it’s development, growth, marketing pages, messaging, when you’re a small business owner, you figure out what patience is really fast.

Coach Tim Campsall: I learned, or, my, coach, when I first started said, it’s all about persistent and consistent. And then I added patient because I’m naturally an impatient person. And we, I was at a conference this last week and my, Business coach was in from New Zealand and he put up a picture of three mountaintops one, one after the next and said, Hey, this could represent what your three year growth plan is.

But the reality is no one if you use the Bye. Climbing Mount Everest as an example, no one can just scale up to the top, zigzag back and forth because you have to climatize and adjust and adapt. And he did, that’s the same with, getting to your year one goal and your year two goal and your year three goal is there’s a whole bunch of zigzags because you have to learn and grow and develop and test and measure and trial and error and figure it out.

And so my takeaway from that was just embrace the zigzagging.

Steve Iskander: And that really is. It took me a very long time, much longer than I’d like to admit to, especially on camera on the, it really is almost embracing the suck if that’s in triathlon or small business to endure it. And then it is not, it’s right.

10 years to be an overnight sensation. Yes, it truly is a roller coaster ride. And it really is a lot of sitting back and enjoying the ride, knowing that it is part of the ride. And. You’re not always going to climb vertical, as you say, there’s going to be a lot of loop de loops and punches in the face that you’re not.

It reminds me of that game wipe out. If you remember that back in the day, wipe out. I’m like, that’s a small business owner right there running across that.

 You don’t have to be an athlete to make it across a small business owner, but it is embracing the, yeah, there’s a better day coming. And if I stick to my plan, I’ve got surrounded by good people.

It will change and that bottom of the loop will take me to the top of the hoop and get me over the mountain.

Coach Tim Campsall: Yeah, the other thing somebody shared in the audience that climbing a mountain to stay on that analogy is Sometimes you go higher And then you come back down for camp and you stay overnight at a lower altitude so that your body can acclimate and adjust And I thought that was also really insightful of yeah when our business shrinks It doesn’t mean we’re failing means that we’re preparing for the next growth spurt

Steve Iskander: And a lot of what I share with my team, I’ve been very blessed that the team that I’ve had or I say I had, I have the team I have super fortunate.

They are rock stars. I tell them probably a little too much on how much I love them, how amazing they are, but. It is a truth. And a lot of them have been in startups themselves. And I say again, let’s stop worrying about what could go wrong. We have the ability to write the story that we tell later.

Yes. We can gather that. Let’s not worry about telling the story on why we failed or what went wrong or the perfect storm, let’s really focus on what do we want that story to be, that we tell six months or six years from now and particularly for me, I am, I’ve got a board call tonight at six o’clock.

Okay. And I am excited to tell the story about what has happened and within the organization since the last time. So that also helps motivate me to from I don’t want to say a hidden benchmark, but a little bit more drive of We control the narrative. We control the story. If we don’t want to say we’re failures as easy as it sounds.

Let’s not be failures

Coach Tim Campsall: Yes, yes the law of attraction. It’s real it works and what we think and believe is what happens So steve we know business success doesn’t you know happen in isolation. So tell us about a challenge you’ve had Over the years and maybe a fellow business owner or a colleague came alongside you and helped you through that.

Steve Iskander: Yeah, that’s I think staying on the small business side and especially for earlier first time founders, I think for me, it’s really letting things go of the, and I say, letting things go from a responsibility, you’re not going to climb that mountain no matter how great, how much endurance, energy, stamina you have by yourself.

And you’re going to have to learn to delegate it and to let things go and ask for help. Again, it’s that story. Every, I think a lot of people were in that. I want to write the story. I did this on myself by myself. I figured it out on my own and it took me, at least for me, a very long time to realize that, and then realize there is a tremendous amount of help out there.

And I can learn from Tim’s of the world that have already been punched in the face, that can help me dodge that punch next time. So I think a lot of it comes down to my self reflection of realizing. I’m not going to get there on my own. I’m going to have to hand things off. It’s not going to be exactly how I wanted it to be or perfect.

But for us to move forward as a company, as in a team, that’s going to have to happen, it won’t be. One man show here.

Coach Tim Campsall: Love it. Hey, I’m going to put you on the spot here a little bit, Steve and ask you to pick three people in your business owner journey that you’re most grateful for them being there for your businesses growth.

So who are those three people and how they help you?

Steve Iskander: Business growth? First and by far, definitely my father learned from right as a little kid watching him work on companies trading in the stock market, talking about companies trying to negotiate across the table from him at cheese to give me, by far probably one of the wizards is still follow a lot of his advice and.

I always think, okay, what would my dad do at this point? And even as old as I am or young, how would he, at what questions would he ask? And see, that’s by far number one. And then there’s a lot of guys that I look up to from Andrewthat hasn’t been a business owner himself, but has very high insight to business and understands business to some of the guys have just been good, true partners and allies of mine. Jeff Mills at TF trucking in town, watched him go through the loop de loops of business over the last 10 years to becoming a very good friend of mine from financing his first truck 10 years ago to where we are together now.

And really watching. That side of it, the Chad Hendricks brand out comes up in Wisconsin. Brendan Williams, Indiana Testing Inc. Taking over a family business and then scaling a family business and not just doing it from a Midwest side of it, but nationwide and under learning what he’s done.

And again, the list goes on and on. Tom Wears, from I grew up in the Logan sport as I started. And I remember as a little kid going to the Weir’s truck dealership, semi trucks and looking at trucks when I was a little kid, right? You’re a little boy. You’re like, these trucks are awesome. And to later in life, being able to, I say, work alongside of him for him to give me advice.

And he’s one of the first people that said, Steve, one of my biggest regrets in life is not having mentors around me as as I try to do it on my own and not getting a mentor group around. And that’s always resonated to really see how much his business has grown and really look up to him from again, the 12 year old little kid, look, trying to honk the horn in the same way.

I’ve been extremely blessed and fortunate on that side from really trying to surround myself with. a lot of different types of people, different people to really help propel me. And they were the ones that if they’d been the cheerleaders, they’d been the small business owners themselves and been punched in the face.

Coach Tim Campsall: As you think about the future the next one to three years, what’s your number one priority or the challenge that you see that you’re going to need to overcome to achieve your goals?

Steve Iskander: A lot of mine, I’m focusing on the mental growth. Most people I, for my own vulnerability, don’t know that about me, but from my own it’s uncuffing the mental aspect of what’s really holding me back.

Am I making an excuse or is that really a roadblock and what are the things that I can get through it and challenging myself from a mental stand, a mental side of it, do I really have what it takes? Am I really comfortable being uncomfortable, but do I dream big enough? For me, I think some of the motivation isn’t assets that I see of others.

And let me explain as I go out on the Miami and I go out and see all the big yachts. It’s amazing. And it’s not that I want one, but it’s motivating to me to think, am I thinking big enough? Am I thinking about my business big enough? Am I just staying in this little segment, this little niche? Am I separated from, all these different verticals out there.

How do I really think big? Because this person probably didn’t win the lottery, right? Maybe it’s family money, but it was earned a family money somewhere along the ways. And they thought big. What are the things that I’m doing that make me think small? And I think it starts mentally for me. And I’m not thinking big enough.

I’m not. So I commend even some of the, for me, the far fetched, the Elon Musk’s of the world. And I think some days I wish I drew, I dreamed as dreamy as he has.

Coach Tim Campsall: Yeah.

Steve Iskander: Yeah. It’s working.

Coach Tim Campsall: Absolutely. Yeah. I’ve been in a mindset program for the last three years and I’ve done the exercise of mapping out my revenue versus where my mindset was at.

And there’s a hundred percent correlation, right? The whole idea of, I mentioned it earlier, law of attraction, right? What we think and believe is what we ends up happening. And I can see where my, my, where I, my mindset was strong and healthy and really thinking big, the business was growing where I got tripped up on self limiting beliefs or blocks, right?

The business would, would shrink or plateau and it, yeah, it’s mindset is everything. It’s amazing.

Steve Iskander: I 100 percent agree with that. And for me, that’s where triathlon comes in. The triathlon helps give build up. I say the endurance side, the mental scarring side of it, but even the confidence side of I can do this, I can figure my way through it.

I’ve done this before. I have experience and there’s coaches, right? There’s business coaches, there’s triathlon coaches, everybody in between there that can help me figure it out. So for me, I’d say that’s the uncuffing I need to do is Really dream big. Awesome.

Coach Tim Campsall: I love it. Last question, Steve, Jim Rohn, amazing business guru says that we become the five or the average of the five people that we spend the most time with.

So as you reflect on his quote, what advice would you have for business owners who are trying to do it on their own?

Steve Iskander: What advice? If it’s the advice, I say take it from me and everyone else is that you’re not going to get there on your own ever. It takes a very long time. Don’t waste your time on trying to figure it out on your own. It’s going to take an army. It takes a village to start a small business.

If it’s a one man person or one, one person show to again, 5000 employees or larger surround yourself with the good people. They’ve already been there. They’ve done that. They’ve been punched in the face. They understand it. It’s clear. It’s easily the hands down the cliff notes, the short shortened version of of business growth is you can skip around the board of a monopoly much faster if you just take advice and surround yourself with good people.

Coach Tim Campsall: I love it. Thank you so much for your advice. You mentioned it earlier that you’ve been blessed with some incredible people in your business owner journey, if they were all here on the show today, what would you want to say to them?

Steve Iskander: Oh, thank you. It’s a thank you for believing it in the motivation for being able to help me think through things make me think larger On things keep me on earth at times as well.

So there’s both sides of it, but without them Intrepid wouldn’t be here today. I’m super blessed and fortunate of it again my team my board members They believed in it and continue to go and help us advance the company Hands down. I wouldn’t be here without them I’m very concerned about actually where I would be telling a much different story without

Coach Tim Campsall: Awesome.

Steve. It’s been a pleasure speaking with you today. Thanks for being on the show.

Steve Iskander: Yeah, absolutely, Tim. I appreciate having you being on your show and everything you do for the community, man.

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