Hard Lessons I Learned the Expensive Way

Most lessons in entrepreneurship don’t come from books—they come with a cost.

In this episode of Robert the Realist, I talk honestly about the mistakes that shaped me as a business owner. The deals that didn’t work. The opportunities I chased for the wrong reasons. The times I said yes when I should’ve said no—and what it all cost me in time, money, stress, and perspective.

This isn’t advice. It’s experience.

No hype. No hustle culture. No pressure.

If you’re building something of your own—or questioning decisions you’ve already made—this conversation is for you.

Robert the Realist

Real life. Real business. No pressure.

Transcript

SPEAKER_00 0:00

Hello my peoples. Robert the Realist back here today. Today, we are going to talk about hard lessons I've learned the expensive way. Let's talk about it. So to start, when I got in the insurance business in 2007, I started commission-only based insurance business. I found that, like I said, in the local paper. I did that for, I don't know, two or three years. And uh I never made $100,000. I think the first year I made about $65,000 or $66,000. The second one is uh about $67,000. Yeah, $67,000. Um I was agent of the year, rookie of the year, my first year. I helped build a team. I helped train people on the phone. Um probably the first I'm not gonna say a mistake, but the first made a merge first move that I made that was expensive was I was recruited by another insurance agency or insurance company, insurance carrier that sold the same type of products that were a little more well known. And the goal for them was for me to be their district sales manager. But so I had to go over there and prove myself. But when you leave an insurance uh commission-based uh job, you leave with nothing. So about about 2010, I started over uh with a different insurance company, so I had nothing, no commission. Now, when I left and moved over, I obviously had some clients come over with me and you know it kind of helped boost it a little bit. During my time with that insurance company, I um decided that you know become the district sales manager. Uh, we built out a team, we ended up at a business center for a little while, which was pretty pretty tough to build a team out because it was the separate offices and we had a shared conference room. Eventually, they did build out an office for us in uh village of Cherry Hill in Columbia. Uh by this time, I was uh the sales manager. I probably had a half a dozen people on my team. I'd become a registered principal, somewhat called a you know, financial advisor, um a registered representative and a registered principal, so overseeing those those people there as far as registered principals are concerned. And I did that, and you know, the money was pretty good. Uh I was driving back and forth to Columbia, wasn't fun. I did all the hiring, firing, training, recruiting, calling, interviewing, everything. So I was I was the only one in the office. But uh one day my both of my upper management guys got fired on the same day. Uh and it was a pretty big eye-opener for me because those two ran um our office was like a regional office, so I had multiple states um that that you know made it up. And you know, it was the number one or number two back and forth regional office in the United States of America. So it was a pretty big deal, and they let these guys go. I mean, it was uh it was a gut punch. They were friends of mine, uh, they brought me through the system. Um, I really looked up to them. I had had a great time, I had a good friendship with them, and I knew nothing about it until it happened. So, you know, we won't get into a whole lot of that. I still don't know the whole story, and again, this wasn't my problem. I did apply for the the management position, did an interview, wasn't they? I was quite ready. So they brought on somebody else from coincidentally enough, the insurance agents, the insurance carrier that I was working with prior. And I like the guy and we got along real well. Um, but kind of you know, about a year or so in, they really got corporate-y, and I say that because you know, there was I don't know, four or five of us district sales managers, and we all went to some meeting and they were gonna make some changes, and these changes were pushed up the ladder by a couple um younger adults uh with degrees. Um not knocking the degree, but what they came up with basically told us we were gonna do more or less. And so within 48 hours of that meeting, three, I know three of us resigned those positions. And so guess what? I started over again. You know, when I left there, uh I couldn't get I didn't get a paycheck, I didn't get renewals. Uh was expensive again, number two, um chapter of my life that I had to go through. And I took a month off, and funny subject. I don't think I took a month off. I took a couple weeks off and I redid the cabinets in my house. Yeah, took them off and painted the fronts, etc. Yeah, it's just a little side side story. After that is when Huffman Insurance Group started, kind of started, but it didn't start, meaning I really didn't know what I was doing.

SPEAKER_01 5:17

It was my real me.

SPEAKER_00 5:36

Huffman Insurance Agency was already taken. The only reason I started, quote unquote, Huffman Insurance Group to name is because I wanted to make sure this time when I built the business and I had commissions, etc., coming in from insurance carriers, that if something happened to me, that it would leave, you know, it would stay with the business, and the business would continue to get paid and it wouldn't die with me. So we started it that way. You know, no, I started in life and health, and man, it was a struggle. Um, selling Medicare, life insurance, long-term care. You know, and uh I had to set up and got my desk. I think it was given to me. I had, you know, just a regular push-button phone and some cheap computer with a cheap monitor. I mean, cheapest way you can go. I started on Coat Street. I remember my landlord calling and asking me of rent, you know, if I'd put rent in the mail, and I said I did, and that was a lie. Um, there was times that I pushed it off as far as I could. Uh I did the same thing financially at home, but I knew that I was gonna make it. Um, but so I started the Huffman Insurance Group, you know. Well, at that time it was just me and Robert Huffman. So, you know, fast forward just a tad bit. Um I'm still selling life and health. Um I move in to Reed Street, which is where I wanted to move originally. It's not going bad, but uh I get a postcard from 16 car the other day. From, you know, hey, possibility to get you know property and casualty insurers, you know, your homeowners insurance companies, we can get them for you for a small small investment and monthly, blah, blah, blah, and you can get this or get that, like, great. I don't know, it's for postcards, but why not? Because the mindset, you know, life insurance, nobody thinks they ever need it. They need it, but it's typically 65 and above. Um, and that's a business that kind of turns, meaning that they have different companies, other companies that's kind of going back and forth, nobody thinks about care. But you know, people need auto insurance. People need home insurance. These are these are needed items, and then I can talk to them about the other product. So I was trying to kind of squeeze into that market anyways, but it wasn't part of my big plan for this, and I didn't have a plan to this right then.

SPEAKER_01 7:59

So I could buy what I could do to make a bit of dollar.

SPEAKER_00 8:05

So I answered the postcard, talked to um Henry. Um that was Hammy and the wife did, and we thought it was a great idea. But guess what? The investment was very minimal. I had to go to the bank tomorrow. But fast forward. So we so we get everything done, we get everything set up, we get these to get these codes as in column with these insurance codes, which I never would have done in my never would have done on my own. Now, uh definitely more than I think kind of when Nathan came along. We got you know, just just a God moment that we met. A mutual friend, and then his wife spoke and speaking to her, and then he was trying to get married down this way looking for a different insurance position. He was a well-qualified insurance agent. He had spent seven or eight years with uh insurance area that knew what he was doing, so all the big guys, you know, just a car and stuff. We talked about him anything, but uh told uh you know auto insurance a little bit with various in the last five or six years, and all these is totally new to me. So yeah, but I don't have an offer about I never thought for a moment get a phone call, or I can't remember this phone call, or something. Yeah, I think I want to join your agency. Yeah, so they can offer anything to offer you. I can't give you a draw, I can't give you a pay, we just gotta build this thing because that's exactly what I want to do. I don't want uh stresses of people over the top of me telling me what to do. I don't want corporate America telling me how to push this right now. Let's do this because I put myself financially in a good place to do that. So God blessed me with Nathan and He's kind of been my writer died since we started then we actually had quote unquote health and insurance agreement. Um so yeah, that's that's kind of where that started off, and then Nathan and I built it from there, and then from there, you know, a few insurance agents and a few uh people paid rollers come and go. And those are lessons that you learn and friendships that you know that sometimes get harder by friends and family, etc., and businesses the best way to do it. It's not always the best way to do it. When I look back at those, yes, there were some definitely I wouldn't do anything in the past would be 15 years this year I've been in the insurance. I wouldn't change anything the way it's done. You have to remember this. That you know, people say, Would you do anything differently? It's no because how do you get where you're going without going through what you've already done? The people that I've met at all the insurance carriers, all the trips that I went on, all the big meetings I went on, the knowledge that I took other people, the the basic common sense of insurance, etc. etc. etc. I took all that and was able to build what I've got today. I didn't do it on my own. It was gone. Me, I used to say I steal it from other people, but I borrow this information from other people. I've always been since day one a student of the business of a businessman, but so I don't know. Whatever it is I'm a student business, real estate going more four told you about year two or three in real estate, I would have told you what was happening. This was it's it's brutal. This is the realist, right? The real estate brutal. You're being your big insurance agency doesn't like it, right? They smeared me, they made up things, uh and I made it through it, and I'm still here. Some of those have moved on, some of those are still here, and we're you know, we usually get along with the same thing with the real estate. Once you hear it, but again, there's a lot of real estate agents, and there's not a I mean, there is a lot of real estate, but if you do the numbers, 80% of the real real estate or sorry, real tours won't even produce, buy or sell a house for anybody in a year. So it does kind of make it a dog eat dog world. It's the top two or three percent that produce. So it's it again, I'm just speaking from the entrepreneurship side that the business is tough. It takes a lot to crack, it takes a lot to get in, it takes a lot to unstrack, it takes a lot to basically get where we're at right now, which we're just humming along. Um, so I've made a lot of mistakes, some expensive, some heartache, uh, some both. And so if you can take anything from this podcast, please let me let me tell you that nothing in life worth a cry is easy. Okay, guys, so hopefully I appreciate that uh you you stayed with me this long. And uh again, uh subscribe to this. I'll probably check these things out a lot easier because I'm actually set in myself. Appreciate you guys trying to do that.