The First 100 | How Founders Acquired their First 100 Customers | Product-Market Fit

[Bootstrapped] Ep.120 - The First 100 with Bradley Flowers | The Art of Podcasting

December 24, 2023 Bradley Flowers Season 3 Episode 34
The First 100 | How Founders Acquired their First 100 Customers | Product-Market Fit
[Bootstrapped] Ep.120 - The First 100 with Bradley Flowers | The Art of Podcasting
Show Notes Transcript

Bradley Flowers is the founder of Portal Insurance based in Mobile, Alabama, a scratch-independent agency he founded and is building on the back of social media, personal branding, content, and technology. In 2019, Portal Insurance was named the "Agency for the Future'' by Safeco Insurance for the Southeast United States. Bradley is an acclaimed speaker in the insurance and real estate sector and is the co-host of the “Insurance Guys Podcast,” the most downloaded podcast in the insurance industry, which is featured on iTunes, Spotify, Soundcloud, and iHeart Radio. 

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Let's do it. Broadcasting from around the world. You're listening to the first 100. A podcast on how founders acquired their first 100 paying customers. Here's your host, Hadi Rodwan. Bradley, good to have you on the show. How are you doing today? I'm absolutely honored to be asked to come on. Thank you very much for stopping by. I know you're more accustomed to be on my side because you have your own podcast. You're asking the questions. So we reverse the order, but let me introduce quickly. Bradley Flowers is the founder of Portal Insurance, which is a independent agency founded and is building back. of social media and personal branding and content and technology that you have done. And you are also the co-host of the Insurance Guys podcast, which is the most downloaded podcast in the insurance industry. You can find it on iTunes, Spotify, SoundCloud, and iHeartRadio. To go back to your early days, Bradley, did you exhibit any signs of entrepreneurship as you were growing up? That's an interesting question. So I had a dad who... owned his own business. My entire childhood still owns and operates that business today. My grandfather was in sales, and my other grandfather owned his own business. So I guess I was just around it. You know, as a kid, I was always trying to sell something, whether it was a bicycle that was too small for me, or candy bars to raise money for field trips at school. So I think it was sort of just in me. And when I came into the workforce and... got a job or a couple of jobs, I got to the point to where I just felt like I couldn't breathe unless I was the person in charge and just felt like I was being suffocated because I was working for somebody else. And that's not the case for everybody. I guess that's the answer. Take us back to the founding of Amon. How did you enter into the insurance world and to build the agency? And how did you enter to the podcast world to build the number one podcast and insurance? Yeah. Funny enough, the podcast came before the agency, not the other way around. I got started in the insurance industry. I was on the life insurance side of things, which I'm sure some of your listeners can appreciate. And I had a buddy who was doing it. He appeared somewhat successful. I had a very unconventional first day in the insurance industry. I was doing a ride along with him. And I think, admittedly, he wasn't a super hard worker. And I haven't told this story ever on a podcast, I don't think. We did an appointment that morning, and the company, so I probably shouldn't tell this, so the company that we were working for had this promotion where if you got another licensed person to apply, you got 500 bucks. And so he was going to interview his friend who had no intention of taking the job so they could split the $500. So that was my very first appointment in the insurance industry. and then we went back to his house and watched Reservoir Dogs. Mark, not Mark Scorsese, who's the director of Reservoir Dogs anyway, doesn't matter, but watched Reservoir Dogs. And then we went on an actual point, because that was my first day, I was like, this is kind of a weird job, but started there and then fast forward, I went to work for a large PNC carrier here in Alabama, Alabama's version of Farm Bureau basically, worked for them for three and a half, four years. I met Scott, who is my co-host now for the Insurance Guys podcast. And podcasting was sort of the one facet of social media that I had not checked the box on yet. He was like, hey, I think we should do a podcast. We're really good together. And our personalities could not be more opposite in a lot of ways, so it works on camera because we have a decent chemistry. But we agree on a lot of things too. And I was like, sure, if you pay for it, I'll do it. I had no intention of really... really doing it, but I'm like, hey, if you want to pay for it and you want me to be a part of it, I'm happy to do it. So we started a podcast that quickly took off. That's actually what led to the agency to me starting my own agency, which normally it's backwards. Normally you start a company and then you start a podcast to compliment that company. Mine was the complete opposite. So from the podcast, we got to met a lot of very successful characters in the insurance industry, whether it be CEOs of agencies or CEO of carriers or startup founders, tech companies, all that sort of jazz. I would try to implement some of the things I learned at the company I worked for and obviously got met with corporate red tape because I was just a peon corporate employee. I was like, well, screw it. I'm going to start my own agency. Started the podcast late 2017. I left and started my own agency March of 2019. Amazing story. If you look at the podcasting world today, What's an average investment you need to start a podcast and how did you select the topic and the niche around it and what's the average listener going to expect from an episode that's done by Bradley? The beautiful thing about podcasting is you don't really need a ton of equipment to start. I mean really all you need is your cell phone. You can record on voice notes on your cell phone and as long as the content is good, people are going to listen. You know what I mean? But the flip side of that is to have the top of the line equipment, in my opinion, two grand, I mean this mic is 400, almost $500 that I'm using, that's the most expensive piece that I have. There's tons of options for every price point, so you can kinda go a little bit crazy and not spend too much money. The cost though is in the effort and the execution. and the time you have to put in, whether it's editing yourself or hiring you on editor and that sort of thing. So really it's a minimal, it's more of a sweat equity investment. And I'm sorry, I forgot the second part of the question. In terms of how you select the topic and what's the expectation of the listeners. So you went with the insurance specific topic, but how do you select the topics, the guests, and eventually what's the expectations of the listeners? Yeah, absolutely. So we are very selective when it comes to guests. We are very protective of our audience. I see other podcasts out there, and you can tell they're just basically interviewing anyone who's willing to be a guest on their show. It's very obvious in some cases. So like for us, we really try to dive into what is the intention of the guest? Are they trying to sell something? Are they trying to pull some of our listeners away from our audience over to theirs? Or do they genuinely wanna help? and we tend to default to people who genuinely want to help our audience. And then we also try to cut through the bull crap of people who actually aren't successful and are just putting on a facade. There's some folks that I haven't interviewed that other podcasts have interviewed, just to be blunt, because I don't know that there's really any substance behind the scenes there. And that doesn't mean I'm right. It's just all things aren't checking out. in my head for that. You know what I mean? So we try to really run our potential guests through that gauntlet. And I would say 80% of the time we start guest first and then, okay, Mr. or Ms. Guest, what do you want to talk about? What are you an expert in? What have you not talked about on the other podcast? And that's another thing we consider too. If somebody's been on... three or four podcasts recently, we won't have them on because I don't want our listeners to feel like they're getting the same thing they are from other podcasts. Kind of when you see a celebrity doing a media tour and they're on every single morning show for three weeks straight, like we don't want that. And you know, that's different because that's live, that's not really prerecorded and posted later. If you're a fan of Good Morning America, you might not also be watching The View, you know what I mean? So that's a little different. Whereas podcast episodes live in perpetuity, they're there forever. So that's number one, and then I would say 20% of the time we have a topic in mind and then we go find a guest who's an expert in that space. So for example, parametric insurance is something that's big on my mind right now. We're currently looking for an expert in parametric insurance. We've had a bunch of people reach out about it, but they're all trying to sell something. I would rather find the expert in that that's not gonna get on there and say, oh, well, if you wanna know about parametric insurance, you should sign up with our company. You know what I mean? So there's a lot of that kind of stuff that goes into it that the listeners don't see. And it's all in the spirit of protecting our listeners. We want them to feel like when they listen to the insurance guys that they're getting something unique that they're not getting anywhere else. And if it is a guest they can listen to somewhere else, it's going to be a different perspective. Amazing. Thank you for sharing this. And I think a successful podcast is a combination of great content. great hosts who are asking the right questions and definitely great guests. So if we decipher this, if we're looking at the great guests, how do you currently find your guests? What's your process? What has not worked for you? What has worked for you? Because you've interviewed quite great individuals like Gary Vee, Dave Meltzer, Jesse Cole, just to name a few. So walk us through your thought process and how do you land these big names? It's interesting. I had to spend two to three paragraphs in the DMs explaining what we were and what we were doing. And it's been an interesting evolution to where now in the industry, at least, the podcast is somewhat synonymous with my name so I can just say, hey, you want to come on the podcast and they know exactly what I'm talking about. But 99% of us done through DMs on Facebook, Instagram, LinkedIn, Twitter. I remember we booked Tom Hagna who was at the time and probably still the top booked paid speaker in the industry and people were like, hey, did you reach out to Tom's agent? Did you? And I'm like, no, I sent him a message on Facebook and said, would you like to come on my podcast? And it's gotten a little tougher because there's so many podcasts right now, but four or five years ago, if you reached out and said, you wanna come on my podcast, most people said yes, free media. And then Jesse Cole spoke at an event that I was at. that I hosted actually. So he and I got connected through there. Gary was an interesting one because I spoke at Gary's agent 2021, which just so happened to be the same week as the conference that I hosted that Jesse Cole spoke at. Gary also spoke at that. So I had this like triangulation going on with Gary and there's not many guests that are bigger than Gary V for any podcast. And so I always long play relationships. I default to building the relationship first rather than going for the ask or going for the right hook because at the end of the day, a relationship is better than anything else. What we did when I got asked to do Agent 2021, it would be natural if Gary V is hosting a conference for the podcaster that he asked to speak at the conference to ask to have him on their podcast. He's expecting that we did not do that. we interviewed Kim Garcia, who was the person hosting the conference. So it was a little bit of chest, not checkers. And Gary listened to it. He told me in person, he listened to it and he shared it. They were really appreciative as was she that we had, and she's a freaking badass too, by the way. Like we had her on, so we did that. And then fast forward to the week of those two conferences, I got to have dinner with Gary. And once again, everybody's expecting the right hook. And I'm like, no, it's more important to me that he knows who I am rather than just agreeing to do a 10 minute spot on my podcast. So we had dinner, didn't even bring it up, but through that process learned who sort of the right people were. And then when I did make the ask, it was like I had this relational equity built up that they were like, yeah, sure. And in fact, we'll give you 45 minutes, not 10. And I'm like, can I come to New York and do it? They're like, sure. So some of the bigger guests, it's always a story like that. But the smaller, not the smaller guests, I mean, I think people get more value out of a really successful insurance agent than they do at CarryV, but some of the more lesser known guests, we just reach out and ask. I'll tell you how it doesn't happen. It doesn't happen by people sending me a cold DM and saying, hey, I want to come on your podcast, unless they really have something super important that they want to talk about, because 99% of the time, if you reach out to me and you say, hey, I want to come on your podcast, I'm running it through the filter of what's this guy or gal trying to, what angle are they playing and you're going against the current from the get-go. You'd be better off just reaching out, let's build a relationship and eventually if I think you're interesting enough, I'm going to ask you on. But how it really, really doesn't happen, I'll give you a tip. If anybody listens is trying to do this, I am super, super against these podcasts booking services that you pay $200 a month to pepper the market. of all the podcasts to ask people to come on. I've never booked anyone off of one of those. And in fact, this is to tell you guys who are booking these podcast booking services how what a bad job these guys are doing. We interviewed a guest, his episode dropped. Two weeks later, I get an email from one of these asking me to book him and I'm like, you're not even taking care of this guy, you know? That's not to say that people that hire these services are bad, I think the services are bad. So anyway, sorry for the long answer. I mean, it's a funny story that you've shared this because actually I had the same issue with an agency, but actually there's two funny stories. The first story is I had a guest, I interviewed him, and then they reach out to me to book him again on the podcast. And the other funny story is I have a guest booked in January. And the company reached out to me thanking me for doing the episode with that person and asking me to share the episode even though I haven't yet recorded it. So as you said, probably it's a service, not the idea behind it. So thank you for sharing how you do it. Let's move to the other side where, you know, the listeners, which is how does a podcast attract enough listeners to matter? Because yes, you have great questions, you have great guests, but if no one's listening to them. then at the end of the day you get demotivated because it's a lot of effort as you said. So how did you start and what channels worked for you the most? I think you need to do at least a year's worth of episodes, whatever a year is for you, whether it be 12, 52 episodes, what have you. I think you need to do it for a solid year before you ever worry about downloads or listenership or subscribers or anything like that. You just put your head down and put out good content. We had a buddy who started a podcast and he did it a month and he called me after a month, freaking out. Like absolutely freaking out because he only did 200 downloads. And I hit him with all my usual lines if somebody's worried about reach. And I say, look, you know, if you had 200 people in your office sitting there saying, Johnny, we care about what you have to say. We want to sit here and listen to everything you have to say. That would overwhelm you, right? That didn't work. We need to keep at it. You need to put your head down and put out good content. He was still freaking out. So I said, hang on a second. And I logged into my computer and I pulled up the downloads that we had the first month we did it. And I said, do you know how many downloads we had? And I'd never done this before, by the way. Do you know how many downloads we had the first month? He said, I don't know, a thousand. I said, we had eight. Not 80, not 800, we had eight the first 30 days. One of them was definitely me, one of them was definitely my mother, one of them was definitely my grandmother, and one of them was definitely my dad, okay? So we really had three. And he's like, I'll shut up. I was like, yeah, you gotta put your head down and you gotta put out good content and don't really worry about your reach for the first year. Secondly, the number one way outside of that, the number one way to authentically grow your audience without really doing any promotion, or paid ads, which we've done, we've probably spent $100 on paid ads to promote the podcast. Very minimal. The number one way is to interview people who already have followings. We call that in podcasting, coattailing. You find someone else who has a following, who has some reach, you interview them on your podcast, ask them to share it on their social platforms. That's exactly, if you look at the first 20 guests of the Insurance Guests podcast, they were all very, very intentional. It was all people that had followings, that had clout in the industry. And the flip side of that is, is they have a following, they probably have something interesting to say, which is gonna make your podcast that much better. The second thing you can do to grow it organically is try to get you some sort of speaking engagements in your niche. be willing to speak for free, you get a different audience at a conference. When I speak to conferences, Insurance Guys podcast, as far as we know, does more downloads than any other insurance podcast, and some of us have gotten together and compared numbers, but I can go to a conference with 400 people at it. I always ask who listens to the podcast because I make a joke when not that many hands go up. I was like, oh, but it's usually less than half the room that listens, so that's a huge, that's a 200, 250% opportunity. that I have to pick up more listeners that way and be willing to just put in the work from that standpoint. That's great advice. Thank you for sharing this. I think in 2020, you also did a YouTube series called Making the Donuts, which showcases the everyday behind the scenes of your agency. And you've posted a lot of content there. Couple of questions on this. One is, as you're starting the engagement, they slow the growth of the graduate. How do you... keep yourself motivated to continue posting? And the second question is, how do you leverage multiple channels like YouTube, maybe your LinkedIn, to feed it into your podcast, or is it the other way around? I'll be completely honest with you, I'm as least motivated to post right now than I ever have been since I started creating content in 2015. Mostly that is because the business is doing really well and therefore it's taking a lot of my time. We're growing, we're in the middle of an acquisition right now, so we're gonna double overnight in two weeks, which scares me to death. So I'm just not that motivated to post, although I still am. There was a period of time where I was posting 10 times a day across all platforms, and it was me doing it. I didn't have any help from a graphic design standpoint, from a creation standpoint. Now the content wasn't very good. but I was still doing it, you know. Does the social feed back into the podcast? I would say the social definitely feeds back into the podcast more than the podcast feeds back into the social. Very rarely do you hear us say, hey, follow us on these platforms. You know, our listenership versus the number of people we have that like and follow our Facebook page and Instagram, it's very lopsided, as we would say in the South. But... We should probably do a better job of that, but it's more the other way around. But honestly, man, what keeps me motivated to post even right now as I'm very not motivated to post and create is I have this undying need to just share what's going on along the way. I have this saying, I say do cool things and talk about it. I haven't really said anything about this acquisition because I didn't really wanna jinx it. I didn't want to talk a ton about it and then it fall through and it still could fall through. Unlikely but it could. But after 1-1 if it goes through, I'm going to have a ton of content to share and it's sort of my therapy in a way to like vent and get it out there and then see how the market responds to it and that sort of thing. How I do it on multiple platforms, I think you have to have one or two platforms that you go to first. that are your favorites and that you really understand the context of the audience on there. For me, that's Twitter and LinkedIn. But you need to talk different on each. Now, I think cross-posting the exact same thing is better than not cross-posting at all. But the example I give is, you know, if you and I were to go to a conference today, okay? We get there in the morning, there's a morning coffee and usually they'll have like the CEO of whatever company up there talking, okay. We're gonna attend the conferences today, we're gonna go to dinner that night and then we may go to a couple bars with some people at the conference. That's two different conversations, the opening keynote coffee and the bar. Two different conversations. LinkedIn is the opening keynote, Twitter is the bar. But business gets done at both, and the conversations are valuable at both. It's just a different way of talking and conducting yourself. And so that's how I think of these social platforms. So I think you have one or two that you really feel like you have your arms around, and then you cross post to the rest. So for me, YouTube, Instagram, you're pretty much gonna see the same videos there, trickle over to Facebook and stuff. But they're really the name of the game with all of that is just repackaging, repurposing new and old content. I'll give you an example, my video editor now, who works remote, what he does is when he edits one of my videos, he takes the transcript from the captions and sends those to me in a Google doc. I drop them in ChatGPT and all of a sudden I have a Twitter thread, very easily. It's taking that one core piece of content and there's offshoots off of it. that you can turn into standalone pieces of content. And that's really how you maximize your reach. Especially as like a micro, I don't wanna use the word influencer, but somebody who doesn't have a ton of reach, you really have to do that well in order to reach the correct amount of people. Amazing. One last question. What's the principle that you live by that has served you well in your journey? This is one of those questions I wish I had some time to think about, like a couple of days. One of the first business lessons my dad taught me is don't burn bridges in business. Now, personally, I think he believes that to the extreme where sometimes he doesn't put people in their place that need to be put in their place. And I'm probably a little bit on the other side, but I think if you default to just not burning any bridges, life will serve you well. Makes a lot of sense. Your father definitely is a smart man. Bradley, thank you very much for joining the pod. What's next for Bradley? We are trying to navigate this acquisition, finish that. Scott and I have a company that we are launching that's going to serve agents first quarter of next year. We're really excited about that. So just really those two things are the two biggest things I'm focused on right now. Bradley, we wish you the best of luck. Thank you for joining and sharing your insights on how to build a podcast. Absolutely, thank you. Thank you so much for listening to the first 100. We hope it inspired you in your journey. If you're enjoying the podcast, please subscribe to our podcast on Apple iTunes, Stitcher, Google Play, or Spotify, and share it with a friend starting their entrepreneurship journey. Leave us a five-star review. Your support will help spread our podcast to more viewers.