Scale Like a CEO

Building Success with People-First Leadership with Phil Portman

• Performance Accelerated Learning • Season 1 • Episode 1

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Overcoming Challenges to Build a Successful Business with Phil Portman | Scale Like a CEO Podcast

Join host Justin Reinert on this episode of Scale Like a CEO as he welcomes Phil Portman, the founder and CEO of Textdrip. Phil shares his journey from leaving the corporate world to building successful businesses, including a revolutionary business texting platform. Learn about the importance of a strong work ethic, the challenges of scaling, and the value of investing in people over products. Phil also discusses overcoming personal and professional obstacles and his vision for future leadership and inclusivity within his company. Don't miss this insightful conversation packed with valuable entrepreneurship lessons and inspirational stories!

Phil Portman Website: https://philportman.com/
LinkedIn: https://www.linkedin.com/in/philportman/
Success Is Podcast: https://www.youtube.com/@UCXGujqMa-F2hKdS_BmWHZiA

Phil Portman:

When I left the corporate world, I made a commitment to myself the universe, whatever you want to say, and I said I will never work for somebody else again.

Announcer:

Welcome to Founder to CEO, a podcast exploring the journey from startup founder to chief executive. Join host Justin Reiner as he talks with successful entrepreneurs about their experiences scaling businesses and growing as leaders. Successful entrepreneurs about their experiences scaling businesses and growing as leaders. Today's guest is Phil Portman, founder and CEO of Textrip, a revolutionary business texting platform. Phil shares his insights on entrepreneurship, building teams and transforming from hands-on founder to effective leader. Let's jump into the conversation.

Justin Reinert:

All right.

Phil Portman:

Well, phil, thank you so much for joining me on Founder to CEO. Just to get us, let's jump into the conversation for people who know that texting gets the best results. We found that majority of CRMs and platforms out there were very email-centric and they kind of threw on texting as an afterthought, where, when you look at email, it is a 6% response rate, whereas text messaging has a 45% response rate. So we thought, well, what if we made texting the central focal point of what our platform does and built everything around that, using the 80-20 rule right, the 20% that's going to give you the 80% results. So not only do we focus around that, but we became the absolute experts in it, and when they rolled out 10 DLC compliance in 2019, when you have a company like ours that just live and breathe text messaging the results have been astronomical for our customers. So we brought on companies that were doing email marketing. They flipped to text marketing and were overwhelmed with the responses that they've got, and hence Textrip has grown into the company it is today.

Justin Reinert:

That's amazing and I think you kind of answered my follow-up question which is the biggest problem in your industry and how you're solving that. And it sounds like you're solving it by providing a new medium in text and letting people market through text. I'm curious if there's anything that you would add to that.

Phil Portman:

Absolutely yeah. So not all texting platforms are equal, right. So let's go over that 45% response rate. If you're not getting that in text messaging, then the question should be why? Why are you not getting that?

Phil Portman:

And the problem with texting marketing is there's a lot of underlying things that you don't realize, right. So your provider may say we have a 98% delivery rate. Say we have a 98% delivery rate. Well, their checking is did we send your message off and get an immediate response that says it was delivered? We did check 98%.

Phil Portman:

Well, there's a little bit more that goes on behind the scenes before it actually reads the handset of who you're trying to deliver it to. So we do a whole lot more on the back end actually waiting for the delivery receipt confirmation from the carrier and then tracking it. We use some AI behind the scenes to help us with that, but we have the most accurate delivery percentage, so we track it down to there. The reason we do that is we want to make sure that if your messages are not getting delivered, we know exactly why. We can help educate you and develop our platform to help ensure that you have the best deliverability going forward. Unfortunately, because anybody can make up their delivery response. The only real way to track if you're getting the results is your response rate, and it should be hovering around 45%. So if it's not, come see us over at TechStrip and we'll help you figure out why.

Justin Reinert:

Nice, nice. Well, that's great. So I know you've started a couple of businesses, a successful serial entrepreneur, and so I'd love to talk a little bit about challenges that you've encountered, transitioning from the founder being the one person building this company to then building a team. What are some challenges that you've faced?

Phil Portman:

Yeah, absolutely so a little bit of my background. I left the corporate world. I started flipping houses, did the real estate venture, started a food delivery company. Estate venture started a food delivery company. We franchised that operated across six states and then sold that to deliverycom. Now I'm primarily in the automation and communication space today, going from a founder, a one-man show, to a company that employs 70, 80 people. That employs 70, 80 people.

Phil Portman:

There's a lot of different hats you wear along that path, and one of the things that I had to first start with was myself, and let me explain what I mean by that. I grew up one of seven children raised by a single mom. We were poor. One thing that I had going for me was my work ethic. We all had that. We were raised by doing paper routes at night with my mom cleaning houses during the day. We had that work ethic.

Phil Portman:

Well, when you get to a certain point in your business where you employ people to do aspects of your company, when you have that work ethic, it can be difficult to delegate things off, take things off your plate, because you have this burning anxiety inside you saying wait, no, no, you should be working, you should be doing things. So I'd find myself working on the weekends and the evenings. I'd be messaging my employees and they'd be going well, should I be working the weekend? Should I be working the evening? Should I be working 14 hours straight? And I was creating a bad work-life balance for them, but also I was getting in the way of them performing what I hired them to do right, doing the tasks that I did.

Phil Portman:

So for me it was taking a step back and going look, I can't just deal with this anxiety by throwing work on the top of it. I need to start with the inner work first and deal with that before I can expand my company. And so I would say to any entrepreneur if you hit the ceiling, if you hit this cap, this thing that you can't move on behind, start with yourself. Look inside. Whether it's examining the feelings you're getting meditation, working with a professional counselor, there's something going on inside you that may have worked well in the beginning, but when you reach a point in your career, you have to turn that back on yourself and say, okay, what do I need to show up as to get to the next level? And that was the biggest move for me, and I continue to do it today. I'm continuously looking at going. What does Phil Portman have to do different tomorrow to be the next version that's going to grow this company to the next area it needs to be?

Justin Reinert:

I love that. I think that self-reflection and self-awareness is so important in moving forward and growing, and I think it's such a common thing for founders to start out just grind it, grind it out right and work harder, work harder. And then you hire people and then you're like why don't they care as much as I do, why aren't they working as hard as I am? And you've got to really look in the mirror and understand kind of where you're at and how do you empower the people around you to help you grow the business and get them, you know, as excited as you are about it. What was the decision point of it's time to start building the team?

Phil Portman:

Yeah. So the point when you start hiring to build a team is when you're getting in the way of your business by you doing it. But the food delivery company after I sold it, I decided that in the next version of my company I was going to be the programmer, I was going to develop the product, I was going to do everything myself, almost taking a step back on the next company because I wanted to be more hands-on. I had built a platform with the food delivery company, spent $50,000 on it just to throw it away, did nothing with it Complete waste of $50,000 on this platform that I had built. And it was my own fault. I didn't know enough about software development at the time to managing software development. So with the next company, I said I'm going to do everything, I'm going to learn how to program, I'm going to develop it myself, I'm going to build this whole thing out. So I completely understand it. In hindsight my software engineers looked at what I built and said Phil, you're not a programmer, stay away from that, we'll take it from here. Right? But it gave me great insight on how to build the product, how to do everything on it. So there's great knowledge to be taken from doing the hands-on approach especially when you're a founder, to learn the marketing side of things, to learn the software development, to do the customer service side of things. There's great opportunities there to grow in your business later on when you have an understanding of how everything operates.

Phil Portman:

But you gotta get to a point where you say, okay, if I put somebody who's gonna be an absolute expert focused on just this one area, how much greater am I gonna grow that? And so for me my calendar was filled up. I was scheduled too busy to do everything all at once and things were suffering. So I started off with customer service. How can I take off this customer service component so that my customers can get the quality that they would expect from any company that they've operated? That's owned by Phil Portman and we promise under 30 seconds response time for our customer service, and there was no way I was going to be able to deliver that as a one-man show. So I started off with that and then I built the sales team, we built the software team and we continued growing. As the business grew and as the needs grew we've added employees to those different areas. So for me it was first understanding the inside and out, by actually physically doing the roles and then filling.

Justin Reinert:

Yeah, so kind of figuring out what can I delegate most effectively right now, what's the business need and hearing you talk about kind of doing it all totally resonates with me thinking about my own business and building my own website and standing up my own sales and like doing all the things when that's not the thing that I'm the best at. And so you've got to figure out how you know when you're ready to start delegating those things so that you can focus on the things that you're the best at there needs to be learned on that right.

Phil Portman:

If you jump straight to the delegating part without actually at least trying out dipping your hand a little bit and trying to understand that role, then you can end up setting yourself way back by, for instance, hiring a company or doing something that you shouldn't because you didn't have enough understanding around that area. So I don't necessarily think, especially in the beginning, that it's a bad thing to be as hands-on as you can, because later on, the more that you understand about that area of the business, the more it's going to help you when you're hiring or delegating. The worst thing that I've done in the delegation process is tried to delegate something that I didn't understand.

Justin Reinert:

Yeah, I think that's challenging. I can think of one. I can think of a client of mine who hired a team to build something that they're not familiar with themselves and it's a constant struggle to kind of figure out how like of this push, pull of like, are they doing it right? Am I like it cannot? Can I really just take my hands off the wheel and let them run? There's a lot of trust there if you don't know the inner workings of that role. So I totally get what you're saying of the importance in having your hands in it and having the experience in it.

Phil Portman:

At least a basic understanding. You don't need to be an expert in it, but you should spend a little bit of time at least understanding it.

Justin Reinert:

Yeah, for sure. I'd love to talk about a time when you felt overwhelmed by decision-making, and what strategies did you implement to overcome it. This is a great question.

Phil Portman:

Oftentimes people just look at the success in entrepreneurship, the results, because no one wants to share the struggle, the really bad times when you're developing a company and everything is going wrong. I mean I had a summer and I call it the summer of darkness where everything went wrong. My partner at the time in business said, hey, I want out, so I had to buy him out, took everything. I had to buy him out of the company. Our insurance wasn't covering my son's EBA therapy for his autism. Our dog died that summer. Summer, I mean, it was just one thing after another. And I remember driving in the car with my infant son in the back seat at the time, looking in the mirror, going, did you mess everything up? You left the cushy six-figure job to jump off on your own to do this entrepreneur thing was. I was devastated at the time. I had hit rock bottom at the time.

Phil Portman:

But two things that drove me forward. The first one was when I left the corporate world I made a commitment to myself the universe, whatever you want to say and I said I will never work for somebody else again. The firmness of the commitment that I made, both in my mind and I vocalized it. Nobody was around to hear it, but I vocalized it and said I will never work for somebody else again. And when I had that really tough time, that was my North Star. That was my thing I was focusing on and I said I know there's gonna be waves and winds and all that stuff, but I can still see that North Star and that's what I want. I wanna be there for my kids growing up. I wanna be there for the baseball games. I wanna be there for the family movie nights. I want to be an active part of their life and I want to show them that if they focus on their dreams, they can achieve them too. So that was the first thing that ultimately helped focus and the second thing my work ethic.

Phil Portman:

My back was against the wall. There is no better position to put me in. I was grinding, I was working sunup to sundown. I was on the phone nonstop. We took that company from just barely breaking by to the behemoth that it ended up becoming because I was in such a tough position. And I don't think, if I was in that position at that time, that I would have worked as hard as I could have. And it is amazing what us human beings can do when our back is against the wall, when we remove that limiting belief that says I can't do that. No, this is my cap. This is what I'm capable of. You'd be surprised what you can do when you're massively in debt, when everything's going wrong back against the world and you've got a family expecting for you to provide for them. And that's really what happened that summer. I had my North Star focus that I was working towards and I had all the motivation in the world to make it happen.

Justin Reinert:

That's amazing. I'm curious how long ago was that? About 10 years ago, 9, 10 years ago. Thank you for sharing that and for being vulnerable to share that, because you're right. I think we often talk very publicly about the successes and we don't talk about the challenges. But there's so much that can be learned from those challenges. And we don't talk about the challenges, but there's so much that can be learned from those challenges. And you're so right about what we're capable of. We were capable of so much more than we think we might be if we just push ourselves. And I said something similar two and a half years ago, I think. I said I hope I never have to work for someone again, but I guess I just need to be more firm in that and say I will never work for someone else.

Phil Portman:

It's like the root of decide right. It means to cut off. So if you want to make a decision and say this is the path I'm taking, cut off every other route. You burn the ships. There is no retreat. You're going in this direction.

Phil Portman:

I will add to it, though an out, an idea, a concept. I had gotten my living expenses down to a certain amount where I said I could survive off of this amount, and I was concerned at the time because I was not taking a paycheck and so the savings, the things that I'd come up with, were going to run up very quickly. So I thought how could I generate a weekly income if I had to Now? This was not my long-term goal, but what could I do to get me by until I achieved the dreams that I wanted to? And so I went into a retail store, went to the back end cap, found everything that was clearanced, bought it all and sold it on eBay, and what I found was I could, if I had to, survive off of this. And so in the back of my head, it was like I said I didn't stick to this.

Phil Portman:

This was not what my vision was, this was not my entrepreneurship journey, but it gave me the confidence in the back of my head to say, look, if things got really, really bad. This is not what I want to do, but I could get by on this. And so I think when you start exploring your head and say, okay, I can only do this or that, these are my only two options. Can I only do this or that? Start thinking what else could I do? How could I make this happen? Because when you start exploring and start expanding your thoughts, you realize that there's opportunities all around you, and sometimes little sidebar opportunities actually turn into a great, huge opportunity and a great business concept in the future. And that's actually how the food delivery company spawned itself. It was just this little side project we were working on. We never knew it was going to grow to the size that it ended up being.

Justin Reinert:

What I'm hearing in there is you. It seems like you have this natural ability to just think of contingency. You know you're looking for new paths, different paths, so that I mean you kind of like you say, you burn the ships right, you made a decision, we're moving forward, this is the thing, but you're also looking for multiple routes to make that thing happen.

Phil Portman:

Yeah, you can't get stuck into one mindset, right? You can't get stuck into just one idea. Find the thing that works, explore it Along. That way, it's important to understand your North Star. What's guiding you? What is it that you want? What's going to push you through when things aren't going well, when you're having that summer of darkness?

Phil Portman:

For me, it was time with my family. I had this vision in my head that entrepreneurship was going to allow me to spend time with my kids, go on a weekend trip to Vegas and see the Hoover Dam and Grand Canyon like we just did, and be there for any events that they had going on, because I would dictate my schedule. That was my North Star. That's what I was heading towards. The specifics on how I was going to get there didn't really matter, like we could try out different things to get to that North Star.

Phil Portman:

So I wasn't dead set on this business has to work. No, I was more on the idea of what business model is going to work. But still allow me to achieve my ultimate dream, right? So in order to do that, it couldn't be a business that I was going to work at 12 hour days, seven days a week, forever. I could do that in the beginning, but eventually I'd have to start setting some of that stuff off. It couldn't be something that was going to require me to travel nonstop, because once again I would want to be with my family and things like that. So I had that North Star focus and then, yeah, absolutely, I was trying different things out to figure out what was going to work for me.

Justin Reinert:

So, as you look to the future in continuing to build this and go towards that North Star, what do you see as the vision for the evolution of leadership in your organization?

Phil Portman:

of leadership in your organization, constantly evolving in leadership. If you are not making leadership and communication one of your top focus areas, you're missing out. You should be constantly analyzing your leadership style and communication effectiveness on a regular basis, because the people you're leading and it's constantly changing. The environment's changing. The new generations that we're hiring are different than the previous generations, so we're constantly adapting that. The communication styles, the methods, it's all changing. The face-to-face interactions that we had today, now it's more Zoom and there's even text-based conversations that we're having With that being said, there's two things that I'm focusing on internally in a leadership style, and that's developing leaders internally instead of hiring externally for specific positions that we're trying to fill.

Phil Portman:

So, for instance, I have one of my employees that was a customer service manager that's currently back in school, finishing for a marketing degree that we're paying for because I want to see her in that role, not because she has the specific knowledge around that, but because she has the leadership attributes that I think are going to do really well in that. And then the other thing is I've made a commitment to have 20% of my employees special needs. I believe with that, there's going to take a certain leadership adaptation from me to be able to facilitate that and from the leaders in my company to facilitate that. But that is our goal. That's something that I'm working towards. I want 20% of my employees to have some sort of disability, that we're finding a role for them in the company. So those are the couple of things that I'm working on. I really want to build that internally if we can help them with education, finishing up college degrees or redirecting their path internally, and then 20% of our employees being some sort of disability.

Justin Reinert:

That's so incredible. I love that and I think you had mentioned before before we recorded talking about a shift from product focus to people first leadership, so kind of in that vein. As you think about that, I'd love to hear a little bit more about what was that shift? How did you like? What made you decide to go there?

Phil Portman:

Yeah, I remember having the thought. My mom brought it up when I was thinking about selling the food delivery company and she said Well, what if this is the only thing that you had? What if this is the only time that you'll have found that level of success? And now you're gonna sell it? Right, you struck the lottery with this idea and then now it's gonna be gone and you could have continued building it forever, and I had my reasons why that part of my life had come to an end and I wanted to start a new journey. But in the back of my head I kind of had that thought too. What if this was it?

Phil Portman:

But when I analyzed, when I dug into what made us successful, it wasn't a brand new concept that was different than anything else existed out there. Things like what we did existed out there and they still exist today in the business that I do. I didn't create the business texting platform, the things that we use. They weren't different than other things out there. None of that stuff was different. So what was different? When you peel back the onion and look at what differentiated us in that business, it was the people, and it continues to be the people. The people is the thing that separates us.

Phil Portman:

It doesn't matter if I'm running a text messaging platform or if I started a garbage removal service or if I opened up a restaurant. I have people working for me that are amazing. They're incredible. I trust them and they'll continue with me. They've told me this. They'll continue with me on whatever we get into. Recently it was a 54-acre commercial horse farm, which has nothing to do with technology or anything else we've ever done. My CFO will tell you she knows more about manure removal than she ever thought she would know in her lifetime, right? But it's these people, this work ethic, this trust, this relationship, the communication style, all of that that, if we continue to focus on and build, the results will come. And that's what we found and that's why I'm investing in education for them and growth opportunities for them, because I know if I can help them become the best version of themselves they can be, my company will be as well, and so far it hasn't proved me wrong.

Justin Reinert:

I just absolutely love that you can bring the right group of people together, like you can bring the right group of people together, grow them, let them thrive, and you can do anything. And I love this perspective that you can take on different business ventures. It's not about the product, but it's about the people and doing great things together, absolutely I agree. So, phil, thank you so much for joining me on Founder to CEO. What's the best way for people to contact you if they want to reach out?

Phil Portman:

So you go to philportmancom. I just wrote the three keys to success. If you want to get on there, click the link. You can purchase it from there. We also have the contact page on there, phil Portman. On any of the social media platforms. You'll connect with me via that route as well. I look forward. On any of the social media platforms. You'll connect with me via that route as well. I look forward to any of the questions that you guys have. Also, you can tune in to me on the Successes podcast, where I interview people from just a variety of different backgrounds Could be an entrepreneur, hedge fund managers, authors, stunt woman a little bit of everything to discuss how they achieve their version of success in life, and we find some really interesting stories.

Justin Reinert:

That's great. Thank you so much, bill, and I'll make sure we include some of those links to those resources in the show notes so that folks can get at them. Thank you so much.

Phil Portman:

Thank you for having me Appreciate it.