July 2026

Dave:
When the Great Recession hit, Andy Gill’s business went under. The future he thought he’d created disappeared overnight and the fear of being in that position ever again became his new obsession. So he grinded, he hustled, he faced major setbacks along the way. And in 2022, he got serious about real estate investing. While most people around him upgraded their lifestyles, Andy took extreme measures. He downsized his house, he drove old used cars and he pinched pennies so he could funnel every extra dollar he had toward buying rental properties. Most investors aren’t making these types of sacrifices, but for Andy, it was a temporary trade-off for a more secure financial future and it is already paying off. In just four years, he’s scaled to 58 rental units and counting, and he’s done it all in today’s high interest rate environment without a super high paying job. In many ways, Andy is just the average investor, but he also knows his superpower.
He uses his creativity to cut through the noise, to spot opportunities that fly under most buyers’ radar, and he solves problems for hesitant sellers. Today, he’s even going to pull back the curtain on a genius strategy you’ve probably never heard of, but it’s one that helped him take down a 30 unit property with very little of his own money.
What’s up friends? I’m Dave Meyer, chief investment officer at BiggerPockets. Today in the show we have Andy Gill, an investor in Connecticut who was previously on episode 803 back in August of 2023. And he’s also been one of our most popular speakers at BPCon the last few years. So excited he’s going to be back on the show and hear what he’s been up to. Let’s bring him on. Andy, welcome back to the BiggerPockets Podcast. So good to have you here, man.

Andy:
Thank you. I’m always flattered to be asked and always pinch myself a little bit that I get these opportunities.

Dave:
Well, it’s always great to have you here, Andy. This should be a lot of fun. You have been on the show before, but for people who haven’t heard your previous episodes or didn’t attend your wildly popular session at BP Con last year, tell us just a little bit about yourself, where you are in the country and what you do in real estate.

Andy:
So my name’s Andy Gill. I am on the East Coast in Connecticut, directly between Boston and New York. And we own and operate a portfolio of about 58 apartments currently, all within about 30 minutes of our house. So I’m also a contractor and we’re building new homes, new renovations. I’ve been doing that for basically my whole adult career, so 25 years, but I didn’t start buying real estate. I didn’t understand that owning the asset was the goal until about five years ago. So we’ve been in about four years.

Dave:
Oh, wow. Okay. So you were just doing contractor work for other people, homeowners, real estate investors, I assume, for 20 years. What clicked? What happened that made you realize now is the time for me to start trying to hold onto these assets?

Andy:
I had a really bad business experience that I learned a ton from that taught me that I didn’t understand finance and I didn’t understand a P&L. I didn’t understand any of that. And so I had to get smart. And then I had another opportunity, another mentor and learned how to manage. If you can’t measure it, you can’t manage it. And so being able to project costs and walk it in. And after I kind of developed those skills and people skills, I realized that owning the asset, not just improving it was the path. So we started looking for flips and that didn’t work out. And our first purchase was 12 condos here in Connecticut.

Dave:
So you just went for it.

Andy:
Went for it. I got a partner to go fifty fifty. And yeah, my contracting career, being able to do rinse repeat work, 12 identical condos spoke to me so I could understand. And once I understood one, I understood them all. And regarding the tenants, understanding how rent would move, what the improvements would be, all that stuff, I was comfortable with that. So we jumped in the deep end.

Dave:
What does your portfolio look like now?

Andy:
So we have 58 apartments in various different structures. Amazing. Some we own ourselves, some we own them single partners. And we got into a 12 family with two other partners and they’re all spread. We go as high as Putnam area in Connecticut and low as about Norwich in New London County. And so we manage all of those but 12.

Dave:
That’s a lot. That’s scaling quickly, 58. How did you finance it? Sounds like with partners, but did you have money saved up from contracting?

Andy:
I grew up pretty with limited means and early in my marriage we didn’t have a lot. And my son has cystic fibrosis, which is heavy financial implications. And so it took us a while and I took a real hard hit with that business loss during the Great Recession. So it took a while and we learned to live below our means. And then slowly we realized that we were starting to save. And so we stayed minimal and we drove used cars and we moved to a smaller home and then we had a little bit of cash and we were able to get in with a partner and learned commercial financing. And so that was originally how we went in. We got a commercial loan with a five-year arm and it was a value add. And we created quite a bit of equity in that just by coming in, stabilizing the property.
And then we were able to move some of the equity into other deals. But along the way, once you prove you can do the thing, so if you stay singularly focused on what you’re great at, then people will loan to you. Most of all the financing we do now or most of the loans we get now are private. And so we’ll talk about this deal that we have taken down over the last 18 months and will continue. So like a three-year plan is privately financed.

Dave:
We’re going to turn our attention and talk about this awesome, very cool, unique deal that Andy is doing that I’m very eager to hear about. But I just want to ask you a little bit about that financial sacrifice you made. You said you downgraded, you lived below your means. How did that impact your ability to be a real estate investor? And how do you look back on it now? Was it a big sacrifice? It sounds like it was worth it, right?

Andy:
Yes, it certainly was worth it. At the time, I think it was more out of fear at the time. I was afraid of debt. And now debt being good versus bad and how you define that is different for everyone, but I really just wanted to… I didn’t want to owe anyone anything. And so living below our means was freedom for us. So I didn’t want to have to work to pay for a car that other people viewed as us being well off.That didn’t mean anything to me. Good. So we downsized the house and I raised my two kids in an 800 square foot house. It was still 850 square foot house. And we’re still here now. And so was it a sacrifice? I mean, I guess, but it was how I felt safe at that time. And then I realized that we were growing a net worth with equity and savings.
And then when it was appropriate, then we shifted that into investments. So yeah, I think that living below your means, I think understanding what your overhead is and everyone should look at their personal as overhead and being able to clear that. And I don’t mean everyone, not everyone has the ability to do that, but if you do have the ability to live below your means, you should.

Dave:
You mentor a lot of people, right? You talk to a lot of real estate investors. Do you find a lot of people are willing to do this to sort of reduce their lifestyle even if it’s just temporary to pursue real estate?

Andy:
I don’t think everyone sees the value from a social media high level, okay, this is the life. You buy these things, people pay rent and you make money, lots of money, but it’s not passive. So when you start talking about what it actually takes and the amount of grind and the different steps, so to get through acquisition is a marathon. And then you start and then you meet your tenants and then you have to figure out how to screen tenants and collect rent and do maintenance and what value add you should do and how do you do all this stuff. So there’s a ton of education with it, but a lot of people do not follow through or they don’t see the value in it. I think you really have to want it. And I think that you have to dig in and put some of your wants and desires in the parking lot for later.

Dave:
Yeah. I think that is true. It can become passive, but it can’t be passive upfront. If that’s what you want, you either have to be already really rich and so you can go and be a lender or go invest in syndications or something, or you should just invest in the stock market. It’s very difficult to say, I simultaneously want an avenue, a path to accelerate my financial situation that’s better than every other option out there, like real estate, I believe it is, but I also don’t want to do anything.That is a really hard thing to ask for unless you are fortunate and are already really wealthy. And I just think not everyone has to downsize their house or drive a used car, but you got to find something that you’re willing to give up to pursue it. It’s not free. You have to put something into it.
And I’ve found a lot of younger people are willing to do what you’re talking about. When I started, I was 22. I lived in my friend’s grandma’s basement for three years. I didn’t even think twice about it. It was fine. I was like, “Yeah, whatever. It’s a bed.”
But I do think doing it at the age you’re at when you had kids is something that I hear of less. How long ago was that?

Andy:
We’re in our fifth year now. Fifth year. Yeah. Yeah. We started, I’ll be 49 this year, so I was 44 when we bought our… I mean, we’d done flips earlier. I’d been a contractor a long time, but the first buy and hold, I was 44.

Dave:
Wow. And so five years later, I would assume with what you’re telling me, financial situation trajectories completely changed by making those sacrifices about your lifestyle, but also putting in a lot of work and just sticking with it.

Andy:
Yeah. I didn’t have a 401k. We were just paying for trying to pay mortgage, keep food on the table. And so I knew I had to do something. And so we went for it. I didn’t know I was going to get in when it was still going up. Interest rates were already spiking and I didn’t think it was going to be like this, but I had a belief in myself. I got good at something and I identified the specific metrics that I needed to monitor and watch and it’s gone well. And now when we buy things, we have a good plan and we go to execute it, but if it doesn’t go as well, we know when to let it go.

Dave:
Well, awesome. Good for you, man. I love hearing your story. It’s super inspiring and relatable. It’s something that really everyone can do and just happy for you and all the success you’ve had. Thank

Andy:
You, man. But

Dave:
You haven’t stopped, obviously. And you told me you’re doing a really cool, interesting deal that’s going to really expand your portfolio. And I want to dig into that, but we got to take a quick break. We’ll be right back. Welcome back to the BiggerPockets Podcast. I’m here with investor Andy Gill. Before the break, we talked a little bit about Andy’s background and how he got to where he is today with a sizable portfolio in Connecticut. But Andy, last time you were on the show, you said, I think you told us that you were ready to do something new, but you didn’t know exactly what it was going to be. Now you know what it is, right? So tell us about it.

Andy:
Yeah. So I had an idea. I figured that if I could take under management of properties that I didn’t yet own in older landlords that I knew would be selling that were a bit frustrated, I’d be already controlling the property and be able to be in the first position to make an offer and acquire that property. So I sent out a bunch of mailers that I designed with AI and they were really cool. And it basically said, “Being a landlord sucks, you should sell to me. ” Something along those lines. I don’t remember. It was like cartoons and stuff. And I hit one of my longtime friends and builders that I didn’t know owned properties or I forgot that owned a bunch of apartments. So we talked and I was like, well, he’s like, “My wife is all over me. She wants me to sell.
She wants to travel more, blah, blah, blah.” And I’ve been working with this guy for 20 years. Fast-forward a year and then he’s like, “I think I’m ready to start talking to you about that. ” And so we kind of curated this deal where he didn’t want to pay the capital gains and he wanted to be careful about the depreciation of capture, but he bought a long time ago, so it was pretty minimal. And so I created a proposal where we would transfer properties to me staged over time and he would hold a note and we’d put a small amount down. But I wanted to manage them upfront right away so I could see under the hood and get comfortable just because we had limited capital to take on something this big without partners. So we started doing that and it took a while, took a year to put all together and it was a phased acquisition where we bought some, managed others, and then over time transferred the rest of those into our ownership, into our portfolio.
So we’re about halfway through that now and plans of transferring the remainder in the coming 12 months, I guess.

Dave:
This very cool. All right. We got to talk about this and dig into this. So first and foremost, your thought was if I basically become a property manager for other landlords, I assume you can make some money in it, but you weren’t really doing it for that. You were doing it for deal flow. As those landlords potentially want to sell and offload, they’re going to come to you first and you’ll have early access. I love that strategy. Did someone tell you to do that or did you just think of that on your own?

Andy:
No, that was me. That was my thought process.

Dave:
Wow, it’s genius.

Andy:
Thank you. Yeah. Don’t tell anyone about it, all right?

Dave:
Yes.

Andy:
Tens

Dave:
Of thousands of people are about to hear that idea and copy you.

Andy:
It is. I mean, but it really comes down to would these people hold financing for others? Well, you need to develop the skills so that they would. And so yes, they will if you prove yourself, if you add value. So I take care of problems and I let that be known. And it has become more safe to transfer it to me than anything else as time has gone on.

Dave:
I love that strategy. It makes so much sense. So tell me about the mailers because a lot of people send mailers. I as a landlord get all of them all the time from wholesalers, from people who want to buy my properties. What were you saying that was different than just a normal mailer that goes out?

Andy:
You want to be relatable and approachable in the real world as well as in the perceived world. So I designed a cartoon character of myself and what I do. So I use all the images of… I wear flannels. I’m a very tactile hands-on person. I do my own lawn mowing and snow removal as much as I can. I have to hire a lot of it out, but I’m very hands-on. So I wanted to relay that in who I am and what I do. And it worked. It was like a flannel and a tool belt and a dog and a pickup truck. And it basically said, I’m a landlord too. It sucks. It sucks. You’re probably done anymore.

Dave:
I get it.

Andy:
Yeah. People call you and it must be annoying. Must suck. You should sell to me. So something like –

Dave:
Do you actually think being a landlord sucks?

Andy:
No, I love it. I actually

Dave:
Love it. I don’t either. I don’t think it sucks. All these things are like, “Oh, be a landlord sticks, do passive.” I’m like, “Really?” There are annoying parts, but there’s annoying part of every job. No, I know. I love it. Yeah. Okay. But you’re selling it, so I get it. And especially too, if you’re hitting someone who’s been a landlord for 30 years, maybe they’re over it. And that I could see. And you’re fresh, man. You’re five years in. So yeah, you’re ready to go. I got fresh legs. Yeah.

Andy:
Yeah. Yeah. 49-year-old fresh legs, but yeah.

Dave:
Super fresh. Yeah.

Andy:
And it worked. I got a bunch of calls. I actually got a bunch of calls on that one mailer. I think we sent out like 600 mailers or something like that. And I got 100 calls about it. Wow.

Dave:
What? That’s very cool. I just want to say too, because you’re a big AI user and we’re going to talk about that in a little bit. But I just like that you used AI to be unique in an individual. Because I think if you just go on and use AI and use the template, like you said, that anyone else uses, you’re not standing out. It’s no different than just hiring another company to do it, but you sat down and though about, who am I? How can I showcase myself? And then you use AI to do the execution. That to me, I assume you attribute the success of that mailing campaign and the response rate you got to just by doing something a little bit different.

Andy:
I did a follow-up to that too with a handwritten squasi handwritten letter and it said being a landlord stinks. And I got scratch and sniff snickers of dead fish. And I put them in…

Dave:
It’s the most New England thing I’ve ever heard.

Andy:
Yeah, I did. I bought them on Amazon. It was like scratch and sniff stickers. Yeah.

Dave:
Okay. All right. So anyway, your friend, this guy you know, he calls you. How big is his portfolio? 30

Andy:
Units. 30 units. Nice. It’s a mixed spread. Yeah, it’s spread out over seven properties.

Dave:
Okay. And close in your target area. He’s been doing this for a while, it sounds like his wife wants to travel, but he doesn’t want to sell it today, right? And it sounds like you didn’t want to buy it today.

Andy:
I mean, I would’ve had to bring in partners so I didn’t have the cash to take this whole down all at once without giving up significant equity, which would’ve been fine too, but he didn’t want that.

Dave:
And so what’s the structure? Let’s walk through it. You figured out a way you take over management, that was the first step?

Andy:
Yep. So it was two contracts. So the first would be the management contract for duration of time. The second contract would be for the purchase and sales. Yeah.

Dave:
Did you agree on prices for the sale upfront or was it just kind of like a right of first refusal where if he decided to go sell, you had the first shot at buying it and making

Andy:
It off? Yeah. So the first one we did the appraisals and it went based on that. The remaining ones were with prices to be agreed upon at current market. We actually just agreed on a per unit price because we’re like, “Let’s stop paying for apraisals.” So

Dave:
You just basically said, “You have 30 units, I’m going to pay you. I’m going to make up a number, $100,000 a unit and we’re not going to go and get eight appraisals right now.”

Andy:
Right. Because then you’re like, “It’s fine. You win some, you lose some, but some are three bed, some are two beds, some are in better areas than others. But if you’re taking the whole thing, it made sense.

Dave:
Well, I imagine a big part of the appeal of this to the seller is simplicity. He doesn’t want to spend half of his days right now with appraisers and title agencies and make it simple. And so how far are you into this deal structure?

Andy:
We’re about halfway. Yeah.

Dave:
So you’ve been managing the properties for how long?

Andy:
Coming up on a year now. Managing the property. Yep. It’ll be a year soon and we’ve transferred three of the seven properties

Dave:
And

Andy:
We’re working towards the remainder. Yeah.

Dave:
Awesome. That is so cool. And how are you feeling about the structure? Is it working well for you?

Andy:
It works really well in that for management, it works really well because I’m already in control of the property completely. I already know the tenants. I already know what the problems are. So good. I’m already collecting rent. So essentially I basically just go into rent ready and move it from his account to mine.

Dave:
And do you think the seller’s happy with the arrangement too?

Andy:
Oh, he loves it. He loves it.

Dave:
Yeah.

Andy:
So he’s a builder also. And so now we’re talking about going into development because as he wants to retire, he wants to stay involved and doesn’t actually want to retire. He wants to work less. So we’re talking about developing other rental properties. There’s a thing called an 830G here, affordable housing. And so he’s getting into that developments where we can essentially disregard the zoning regulations and increase density. So he’s into that. So we’re working on some developments that we would partner on also. So we get along really, really well. He’s an awesome guy.

Dave:
That’s so great. Did you follow up with other investors who responded to your mailer? Or once you found this, was that sufficient?

Andy:
I did. There were some in, but they all were just like every other that you get a call from a postcard. So some of them, hey, maybe later, whatever. And so I was keeping a spreadsheet, but then once we got into this, I was like, this is all I can… I’ve bitten more than I can chew right now, so we need to stagger this. I basically stopped. I don’t chase down any deals. I get phone calls on them a lot. Yeah. Oh, good for you. Stuff that if you singularly focus on being good at something, you will get referrals and things will come your way as you develop and grow.

Dave:
That is such good advice and so true. You don’t have to be good at everything in real estate, but if you can be good at one thing and people can count on you for that one thing, it’s going to help your career. Well, congrats, Andy. It’s super cool. I love the approach that you’re taking here. Something I would try to emulate. Maybe not doing the property management, but buying a portfolio. I love the idea. And as you said, Andy is good at this. You mentioned that you manage your properties with RentReady. If you are a BiggerPockets Pro member, you can get a discount on RentReady. It’s an incredible deal. It basically pays for the BiggerPockets Pro membership. If you want to check that out, go to biggerpockets.com/perks. All right, Andy, I want to turn more towards just some advice because I know you mentor a lot of people and help a lot of people with real estate.
I want to hear the advice that you’re giving people to navigate the unique market that we’re in right now. But we got to take one quick break. We’ll be right back. Welcome back to the BiggerPockets Podcast. I am here with investor Andy Gill. We’ve heard a little bit about his background and story and about the very cool, unique deal structure you came up with to really supercharge your portfolio building. You mentioned, and you and I have talked about this, but you help a lot of people build their real estate investing careers. What are some of the things you’re seeing people struggle with? And maybe what’s some of the advice that you’re giving to help people move forward with financial freedom through real estate?

Andy:
The advice I’m giving currently is to be persistent. You have to make a lot of offers. My son is actively trying to buy his first property. Oh, nice.He moved into one of his… He’s 20 years old. He’s got pre-approved for an FHA loan. He’s doing great. And when I watched him make his first offer, you’re emotionally tied to it. So he wanted to get that deal because we picked it apart and it’s not going to be that deal. It’s probably not going to be that deal. It’s probably going to be the 15th or the 20th or the 30th deal that you… And so kind of scan them at a higher level and be persistent and make lower offers. Underwrite without the price in mind with what works for you for cashflow.

Dave:
It’s just about sticking with it right now.

Andy:
It’s

Dave:
Just good. I saw Michael Zuber from One Rental at a time, his community. He was saying that this is the era for low ballers. I like that. And it’s not like you’re necessarily trying to screw people over, but you’re just showing them what you’re willing to pay. And someone will agree to that. At some point the sides will align and there will be mutual benefit, but it’s not going to be everyone. So you just really need to be patient with it. Do you find that’s hard for new investors to accept?

Andy:
Yes, I do. So it’s two part. Be persistent, but also believe in your own abilities to figure things out. So your first deal doesn’t have to be a home run. It just has to get you on base. So if I know that when I get into a deal, if you miscalculate something, if some conditions are discovered afterwards, you’re going to fight through it. And you have to be able to believe in your abilities to get yourself out of jams. So don’t hide behind like, “Oh, well, I need to have X amount of cash flow in order to do this. ” Figure out what would you pay? What would you buy it for? And then find the mean of that and just do it. Get on, get enough, get around people that will validate that, get in the right rooms and then go for it, create a network and swing the bat.

Dave:
That makes sense to me. You said cashflow. Are there any other minimum thresholds that you feel a deal needs to hit these days?

Andy:
For these multifamilies that we’re buying, we have cashflow. We’re already looking for… I mean, cash on cash is… I want to get my money back as fast as possible. I also want to be able to… I want to buy in a place that gets 3% organic appreciation historically. I’m not looking for a place that’s going to just parking money, but that’s not going to grow.

Dave:
I know, but that’s not asking. 3% is pretty normal. So you’re not saying I need to be in Austin in 2020. Yeah, it’s just, I

Andy:
Get it. But when there’s no deals, the deals that are available are typically in the area that you can buy areas that sit flat. Yeah,

Dave:
That’s fair.

Andy:
So stay out of that.

Dave:
And then what about condition of property? Because New England, there’s a lot of old stuff around there. So are there any things you won’t touch or what kind of properties do you look for?

Andy:
It’s funny you say this because the things that are acceptable to me and the things that I see other investors being like, “Oh, I’m afraid of that. ” I mean, I don’t like knob and tube wiring. I want to do that. I like to get a good roof on the place. I want to know structural problems. We have a lot of stone foundations here. I mean, you get out in our basements in New England and you’re like, “Someone was killed here for sure.” Then like, oh, there’s weird stuff. So there’s limited amount of things. I mean, if you look at bad roof structural problems, et cetera, knob and tube wiring, things that cost a ton of money to… I also like sewer laterals. We have old infrastructure here. So there’s your electrical service, your sewer and water. You want to make sure you get that inspected all the way out to the street.
That’s a very, very expensive find later. So there’s a short list of things that I say, stay away from this, stay away from that, or at least get it resolved when you’re in contract.

Dave:
Okay. But would you give that advice for people who might not have your background in construction and contracting? Do you think for people who don’t have that background, you would change the criteria of what to buy?

Andy:
No, I wouldn’t. I mean, like you said, we started this. This is not passive income. If you’re going to come in, you’re going to have to work. And so you’re going to get calls on Saturdays and Sundays and there’s problems that are going to happen. Someone else is not going to come in and buy something better than me at a price better than I can buy and not have the problems that I have. So you’re going to have to figure it out. You’re going to have to go through the renovations, you’re going to have to go through the heavier CapEx problems. You’re going to have to figure it out if you want to be in this game.

Dave:
It’s good advice, man. I like that. Figure it out. You can. That’s being an entrepreneur. You don’t know what’s going to happen, but you can figure it out. You

Andy:
Absolutely

Dave:
Can. Thousands of people have done it. That’s literally the whole point of BiggerPockets too. You run into a problem you can’t solve, go on the BiggerPockets forums, ask a question. Someone will help you. Come to BPCon and you can meet people who can help you. That’s the whole value of having a network. I mean, look at Andy. Having a network landed him this sweet deal with 30… It’s just like you can absolutely do this. Speaking of BPCon, Andy, you had a wildly popular session on using AI with real estate last year. And I understand you’re coming back this year and doing more on AI.

Andy:
Yeah.

Dave:
I think it’s super fascinating because I’ll be honest, I use AI a decent amount, not that much for real estate investing. So tell me what you’re talking about at BPCon and what investors might learn.

Andy:
Well, last year I documented how I use AI, so the different frameworks and how I use it. It was an incredible opportunity. I’m incredibly grateful for it. I never thought I’d speak on a stage with so many people. There was

Dave:
Like 800 people there.

Andy:
Yeah. It was crazy.

Dave:
Andy went viral at the conference basically.

Andy:
Thank you. Yeah, it was pretty cool. It was an experience I’ll always remember. And so this year I was asked to host a AI focused networking session. So the networking sessions at BP Conner, if you haven’t gone to BPCon, it’s absolutely incredible. This will be my third year speaking, I think my fifth show and I won’t miss it. I love the networking stuff and I like how every year it gets more focused on networking. So I’m going to be doing a 20-minute talk on AI and how I use it, but this time focused on other people talking to other people about how they use it. I want it to be of value in the last two years. I really spend quite a bit of time making sure that I want it to be digested really well and people don’t walk away with being like, wow, that was incredible value.
And I beat the hell out of myself to get there. I was super late last year in submitting it. I’m like, “It’s not ready. It’s not ready.”

Dave:
I do the same thing. I’ve always It’s like tinkering till the last

Andy:
Day

Dave:
Of my speech. But yeah, it was super popular, one of the highest rated sessions that we’ve ever had. And yeah, I love the idea that you’re obviously sharing what you do, but AI is so new. It’s interesting always to hear what other people are doing with it. No one has the one right answer right now
And people are super creative about it and I’m super excited to come to this and hear how other people are using it because even just in regular life, I sometimes hear how people are using AI to automate tasks or things they do in their day. I’m like, I never would’ve thought of that. So that will be a lot of fun. If you want to grab your ticket, go to biggerpockets.com/conference. Join me and Andy, Henry and thousands of other investors learning and sharing with one another. As Andy said, it’s a can’t miss event. I look forward to it every year. Super excited for this one in Orlando, October 2nd to 4th. Well, Andy, thanks for joining us again, man. Always enjoy talking to you, learning from you. Congrats on all your success, cool deals that you’re up to. We really appreciate your time.

Andy:
Thanks, Dave. I appreciate it. Thanks for having me.

Dave:
If people want to connect with you outside of BPCon, where can they do that?

Andy:
I am primarily on Instagram. I’m not on the other platforms. Coach Andy Gill, G-I-L A – N-D-Y-G-I-L. And I try to answer all my DMs and I’m an idiot on there and post all kinds of surgery things.

Dave:
No, I like your content. It’s fun. Well, check him out there, Andy, there on Instagram and at BPCon. That’s our show for today. Thank you all so much for watching this episode of the BiggerPockets podcast. We’ll see you all next time.

Bending Spoons, the Italian tech startup, rejects 99.9% of its applicants. That makes it harder to get into than Harvard or NASA’s astronaut program, according to the Wall Street Journal. The company went public last week.

The Milan-based company specializes in acquiring and overhauling companies like AOL, Vimeo and Evernote that have dated software people continue to use. But its real talent is in vetting its employees through a rigorous screening process.

“A run-of-the-mill interview is almost entirely non-predictive, like tossing a coin,” CEO Luca Ferrari told the Journal . “It’s basically completely useless.” 

Instead, candidates take reasoning and judgment tests before anyone interviews them, and a dedicated team of data scientists grades every answer against a hiring algorithm that tracks performance for years after the offer. Even politeness gets scored.

Ferrari co-founded the company in 2013 after his first startup failed and he liquidated it for $40,000. Asked if he’d pass his own hiring test today, he says probably not.

Bending Spoons, the Italian tech startup, rejects 99.9% of its applicants. That makes it harder to get into than Harvard or NASA’s astronaut program, according to the Wall Street Journal. The company went public last week.

The Milan-based company specializes in acquiring and overhauling companies like AOL, Vimeo and Evernote that have dated software people continue to use. But its real talent is in vetting its employees through a rigorous screening process.

“A run-of-the-mill interview is almost entirely non-predictive, like tossing a coin,” CEO Luca Ferrari told the Journal . “It’s basically completely useless.” 

Instead, candidates take reasoning and judgment tests before anyone interviews them, and a dedicated team of data scientists grades every answer against a hiring algorithm that tracks performance for years after the offer. Even politeness gets scored.

Ferrari co-founded the company in 2013 after his first startup failed and he liquidated it for $40,000. Asked if he’d pass his own hiring test today, he says probably not.

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I’ve traveled to over a hundred different countries in my life. Many of these places lack the relative comfort and safety of North America. But I’ve also seen this lack of a social safety net drive people to accomplish amazing things.

Nearly everyone in the developing world is an entrepreneur — because they have to be. The problems they deal with on a daily basis are more immediate, so they’re under greater pressure to innovate solutions.

Most North American founders I’ve met are never truly in danger of falling through the cracks. If their startup doesn’t work, most can move back in with the parents who probably paid for them to attend business school.

But in places where failure is not an option, people work harder to make their dreams come true. I’ve seen it more times than I can count — but the clearest example is a man named Juan Carlos, the first friend I ever made outside the United States.

This is his story. I’m sharing it with you to illustrate what he taught me about pushing through obstacles so that you can remind yourself not to give up when you encounter them.

Opportunities will find you if you’re prepared to acknowledge them

At 15, Juan Carlos hitchhiked from Mexico City to the Mayan Riviera because he had heard that was where people went to earn money. When he arrived, he discovered it would be impossible if he didn’t learn English.

So Juan lived on the edge of town, in a hammock, surrounded by dozens of others, making $3 an hour raking seaweed off the beach. He would walk 12 miles to the city’s downtown area every day to eat in a cheap restaurant because it allowed him to save an extra 50 cents.

With the money he saved, Juan Carlos bought an English-Spanish dictionary. He used his spare time teaching himself how to speak English.

On one of his trips downtown, Juan Carlos met a man who was creating astounding street paintings using the soot from a candle to stain canvas. This technique, called “fumage,” produces delicate, ethereal textures in ways no other medium can accomplish.

Juan Carlos knew nothing about painting, but he knew talent when he saw it. He approached the man and announced his intention to start a business with him, selling the paintings to tourists.

The only person who can prevent you from starting a business is you

Of course, having a business idea is only half the battle. Juan Carlos soon realized he would need a place to sell these paintings if he wanted his venture to succeed.

So he traveled to Plaza Caracol, learned who the office manager was, and asked for a meeting with the plaza’s American owner. The manager was dismissive at first, then outright rude when Juan Carlos continued to make requests.

Still, Juan Carlos continued to visit and politely request an appointment. As luck would have it, the owner happened to be on site during one of these attempts and overheard. He quickly stepped in, and despite his office manager’s protestations, listened to Juan Carlos’s proposal.

Juan Carlos’s dedication impressed the owner, especially after learning how long he had been trying to reach him. They made an agreement: The owner would set Juan Carlos up with a space and the equipment he needed to sell the paintings, but would charge him a small amount of rent on principle. It wasn’t greed; it was a sign of respect — a vote of confidence that Juan Carlos’s business would prove to be profitable.

By the time I met Juan, he had eight people working for him to create fumage paintings and could sell them in no less than seven languages. He never gave up, never took no for an answer, and ultimately created his own success.

Tenacity is more valuable for a founder than any amount of connections

I won’t pretend that founders from the developed world don’t have significant advantages over those who grow up in dangerous or impoverished environments. That would simply be a lie.

But one point I’m trying to make with this story is that founders in wealthier countries often squander those advantages. They let the first rejection or minor obstacle stop them dead in their tracks, when the world is full of people willing to work exponentially harder for even a fraction of the success they want.

Most aspiring entrepreneurs in the United States wouldn’t take the time to learn a single new language — let alone seven — if that made the difference between success and failure. And many would avoid following up with a potential partner after being turned away out of sheer embarrassment or hurt pride. What we don’t realize is that it’s a luxury to have these concerns. Embarrassment is not a factor when you’re sleeping outside in a hammock to get your business off the ground.

Most people who achieve real success respect this because they’ve faced challenges of their own. The owner of the Plaza Caracol didn’t give Juan Carlos his chance just to placate him. He did it because he saw his own determination reflected in Juan Carlos’s willingness to keep trying.

I’ve never forgotten what Juan Carlos taught me about tenacity. It’s what drove me to develop my company’s roof restoration product for asphalt shingles at a time when the rest of the industry was focused on selling replacements. It’s what helped me maintain my belief in the value of our company and grow our national dealer network at a time of unprecedented economic uncertainty. In our present moment, as the global economy is being reshuffled yet again, I remind myself that we can never take our success for granted. The rest of the world already understands this; we’re the ones who need to learn from them.

I’ve traveled to over a hundred different countries in my life. Many of these places lack the relative comfort and safety of North America. But I’ve also seen this lack of a social safety net drive people to accomplish amazing things.

Nearly everyone in the developing world is an entrepreneur — because they have to be. The problems they deal with on a daily basis are more immediate, so they’re under greater pressure to innovate solutions.

Most North American founders I’ve met are never truly in danger of falling through the cracks. If their startup doesn’t work, most can move back in with the parents who probably paid for them to attend business school.

This week on How Success Happens, I sat down with Mamadou Ndiaye, the internet zoologist behind the insanely funny and popular Casual Geographic channel. He’s the guy who turned “animals that can f*cking end you” into a thriving brand, a book, and millions of followers by mixing deep nature research with killer comedy. We’ve broken down his success insights to help you bite off a chunk of success in three, two, one!

Listen here

Subscribe now: Apple | Spotify | YouTube

Three Key Insights

1. Marry Your Two Weirdest Interests

Mamadou didn’t start out thinking, “I’m going to be an animal content creator”—in fact, he actively avoided it because he didn’t think anyone cared about zoology as much as he did. He majored in environmental science (“more asbestos than animals,” he says) and assumed that his love of wildlife and comedy would stay a hobby. His big unlock for aspiring creators: “If you’re able to marry your two biggest interests, then you have the foundation for what could be a really strong channel.” For him, that meant combining a lifelong obsession with animals and a slightly sick sense of humor into one uniquely memorable voice.

Takeaway: List your two strongest fascinations and deliberately build a project that forces them to collide.

2. Ride What Works—Then Systematize It

Casual Geographic started with one “throwaway” TikTok about “animals that are way bigger than you think” after Mamadou saw a moose towering over cars on a highway. That video popped, and instead of shrugging and moving on, he did “the typical TikTok thing where something works for you, you drive it into the dirt”—and that became the backbone of his whole brand. Over time, he evolved from waking up on Monday and posting a finished video by Friday “just off vibes” to a serious creative system. These days, he’s thinking several videos ahead, obsessing over curiosity-gap titles and thumbnails, and crafting scripts to feel like “a FaceTime call” with the viewer. As he put it, satisfying that curiosity gap is one of the most important parts of winning on YouTube.

Takeaway: When something resonates, double down—and then build a repeatable process to keep delivering that kind of hit on purpose, not by accident.

3. Outsource Without Losing Your Voice

For a long time, Mamadou refused to hire editors because “it was my baby” and he didn’t want to hand it off, even as tech issues and editing time started eating his life. Eventually, he reframed it as reinvesting in the channel and respecting opportunity cost: “What are you losing by expending this time? Time is obviously the greatest resource.” Now he works with multiple editors, uses scripts with hyperlinked assets, and deliberately leaves gaps where pros can “cook” while he stays firmly in control of the story. He’s still pushing himself to relinquish more control over time, but sees outsourcing as essential if you want to grow: “There is a middle ground where you can outsource, but still retain a lot of control in the production.”

Takeaway: Identify the bottleneck task that drains your energy and hire help there so you can focus on the creative work only you can do.

Subscribe to the free How Success Happens Newsletter for weekly inspiration.

Two Free Resources to Learn More

You can dive into Mamadou’s wonderfully disturbing animal universe on his Casual Geographic YouTube channel and follow him on TikTok, Instagram, and Facebook under @mndiaye_97.

For more on turning a passion into a project, check how this guy turned one of the most dangerous hobbies on the planet into a thriving speaking business.

One question to ponder

Mamadou talked about marrying your strangest interests into something only you could make. So here’s my question for you: If you combined the two things you’re most obsessively drawn to, what wildly specific project or business would you build?

Email your answer to howsuccesshappens@entrepreneur.com—I’d love to read some of them on a future episode.

About How Success Happens

Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.

This week on How Success Happens, I sat down with Mamadou Ndiaye, the internet zoologist behind the insanely funny and popular Casual Geographic channel. He’s the guy who turned “animals that can f*cking end you” into a thriving brand, a book, and millions of followers by mixing deep nature research with killer comedy. We’ve broken down his success insights to help you bite off a chunk of success in three, two, one!

Listen here

Subscribe now: Apple | Spotify | YouTube

Three Key Insights

1. Marry Your Two Weirdest Interests

Mamadou didn’t start out thinking, “I’m going to be an animal content creator”—in fact, he actively avoided it because he didn’t think anyone cared about zoology as much as he did. He majored in environmental science (“more asbestos than animals,” he says) and assumed that his love of wildlife and comedy would stay a hobby. His big unlock for aspiring creators: “If you’re able to marry your two biggest interests, then you have the foundation for what could be a really strong channel.” For him, that meant combining a lifelong obsession with animals and a slightly sick sense of humor into one uniquely memorable voice.

For years, Portugal occupied a unique position in the global mobility economy.

While many countries tightened immigration rules and raised barriers to citizenship, Portugal became one of Europe’s most accessible destinations for entrepreneurs, investors, retirees, remote workers and skilled professionals seeking a pathway into the European Union.

The country’s appeal extended beyond its climate, safety and quality of life. What truly distinguished Portugal was time.

Five years.

That was all it took for a legal resident to become eligible to apply for Portuguese citizenship, one of the shortest naturalization timelines in Europe. For globally mobile entrepreneurs and families, that timeline became one of Portugal’s most valuable exports.

Now, that advantage is disappearing. Portugal recently approved sweeping changes to its nationality laws, extending the residency requirement for citizenship from five years to ten years for most foreign nationals and seven years for citizens of Portuguese-speaking countries. The reforms also introduce stricter integration requirements and tougher standards for obtaining nationality.

On the surface, this may appear to be an immigration story. In reality, it is an economic one.

Portugal is effectively increasing the cost of access to one of the world’s most valuable assets: a European Union passport. Unlike a tax increase or a higher investment threshold, the new cost is measured in time. For entrepreneurs, investors and internationally mobile families, time can be more valuable than money.

For more than a decade, Portugal benefited from a powerful global trend. As wealth became increasingly mobile, people began searching for stable jurisdictions that offered economic opportunity, political security and long-term mobility. Portugal emerged as one of the biggest winners.

The country’s Golden Visa program attracted billions of euros in foreign investment. Digital nomads arrived in growing numbers. International entrepreneurs established businesses. Retirees relocated. Foreign residents poured into Lisbon, Porto, Braga and the Algarve.

The numbers tell the story

Portugal’s foreign resident population has surged to more than 1.5 million people, a remarkable figure for a country of just over 10 million inhabitants. In 2023 alone, more than 140,000 individuals acquired Portuguese citizenship. At the same time, hundreds of thousands of nationality applications accumulated in government backlogs.

Portugal’s success created an unexpected challenge.

The very policies designed to attract talent and investment also fueled concerns about housing affordability, integration, population growth and the long-term meaning of citizenship itself. As immigration became a central political issue across Europe, Portugal was no longer immune to the pressures facing governments from Amsterdam to Berlin.

The result is a significant shift in strategy.

For years, Portugal competed by reducing friction. The message was simple: move here, integrate, contribute to society and after five years you could become Portuguese.

Today, the government is signaling something different. Citizenship remains available, but it will require a much longer commitment.

That change matters far beyond Portugal

For entrepreneurs, citizenship is increasingly viewed as a form of strategic infrastructure. Just as founders diversify suppliers, banking relationships and revenue streams, many globally mobile families diversify residency and citizenship options. Access to multiple jurisdictions can provide flexibility during political uncertainty, simplify business expansion, improve mobility and create opportunities for future generations.

Portugal’s five-year pathway made it one of the most attractive destinations in that ecosystem. Doubling the timeline fundamentally changes the calculation.

Some applicants will still choose Portugal because of its quality of life, access to European markets and long-term stability. Others may begin exploring alternatives, including Italy, Greece or emerging mobility hubs outside Europe such as Dubai.

More importantly, Portugal’s decision may signal a broader trend.

The past decade was defined by competition for mobile capital and global talent. Governments introduced startup visas, investment migration programs and digital nomad initiatives in an effort to attract people and money.

The next decade may be defined by selectivity.

Across the developed world, governments are reassessing how citizenship is earned, who qualifies and what obligations should accompany it. In that environment, access is becoming scarcer.

Portugal has not closed the door to citizenship. It has simply made the journey longer. Yet the implications are significant. For future applicants, the difference between five years and ten years is not merely administrative. It affects investment decisions, business planning, family relocation strategies and long-term wealth preservation.

Ultimately, Portugal’s new law is about more than residency requirements. It reflects a growing realization among governments that citizenship has become an increasingly valuable economic asset in a world defined by mobility.

For years, Portugal offered one of Europe’s fastest paths to that asset.

What businesses, investors and policymakers can learn from Portugal’s decision is that access, mobility and citizenship are increasingly governed by the same economic principle that shapes markets: scarcity creates value. As governments become more selective about who they admit and how citizenship is earned, long-term planning, adaptability and strategic thinking will matter more than ever for those seeking opportunities across borders.

For years, Portugal occupied a unique position in the global mobility economy.

While many countries tightened immigration rules and raised barriers to citizenship, Portugal became one of Europe’s most accessible destinations for entrepreneurs, investors, retirees, remote workers and skilled professionals seeking a pathway into the European Union.

The country’s appeal extended beyond its climate, safety and quality of life. What truly distinguished Portugal was time.

The Mohican State Park trail in Ohio is nearly 25 miles long. As the only trail in the entire state to hold an Epic designation from the International Mountain Bicycling Association (IMBA), it offers a true backcountry riding experience, with steep single-track trails that abruptly plunge into sweeping river valleys and densely wooded patches alike.

This is not a trail for casual riders. Completing such a trek requires more than enthusiasm; it requires strategy and instinct. You need to anticipate challenges before they appear in your path, conserve your energy for the most challenging stretches and allow yourself to rest and recover when you’ve earned it.

I grew up in Ohio, and I’ve ridden the Mohican State Park trail more times than I can count. I find myself thinking of it often, even when I’m nowhere near my mountain bike. In fact, some of the lessons it’s taught me about patience, stamina and willpower have been most valuable when I’ve faced challenges scaling my business.

My brother Todd and I started Roof Maxx in 2017 to give homeowners a cost-effective alternative to premature roof replacement. Since then, we’ve grown it into an eight-figure business with dealers in every state. But just like any worthwhile mountain biking route, the pathway to getting there has been anything but linear. Here’s what my time on the trail has taught me about how to navigate it.

Recognizing the difference between persistence and stubbornness

Persistence is a valuable quality to have whenever you’re doing something challenging. Whether you’re navigating through rocks and roots on a steep descent through dense pines with no convenient place to pull off the trail or trying to hit a critical revenue target before the end of the quarter, there’s often no room in sport or business to simply stop trying.

But persistence doesn’t mean exhausting yourself prematurely, and continuing to throw yourself headlong at a problem isn’t always the most effective way to solve it. That’s usually the point at which persistence becomes stubbornness, and stubbornness at the wrong moment often has consequences.

Persistence is a commitment to dealing with a challenge. Stubbornness is an insistence on trying the same tactic over and over again until it finally works. The other common name for that, of course, is insanity.

It’s also a waste of resources. Pedaling as hard as you can, even when the terrain will allow you to coast, uses up your energy and leaves you without the stamina you’ll need for the next hill climb. Maintaining aggressive goals for your dealers, even when profits are up, could push some of them to oversell your product and damage their relationships with customers. That’s why Roof Maxx has always worked with our dealers to agree on mutually acceptable minimum targets and give them the autonomy to set their own pace as long as they’re able to meet them.

Going too fast is a recipe for disaster

I’ve seen friends go to the hospital when they tried to simply “send it” on a difficult section of trail instead of planning their approach. I’ve also met my fair share of roofing contractors who overextended themselves by selling more services than they could reasonably perform in a timely manner.

In one case, the result might be a broken collarbone or torn ligament. In the other case, it’s usually a damaged brand. Both can take years to heal, and both could easily have been avoided with a little more foresight and caution.

It’s not always easy to recognize when you’re going too fast, because speed is exhilarating. All you notice is the breeze whipping by your face and the blur of the leaves as you cut through trees; you don’t see the sudden curve until it’s already too late to hit the brakes. Then suddenly, you’re going over the handlebars.

This is why so much of the training Roof Maxx provides to our dealers is focused on effective territory and lead management. We do everything in our power to ensure that dealers know how to effectively plan and schedule the treatments they sell to avoid bottlenecks or service delays. While other contractors in the roofing industry have historically tried to sell as many high-margin services as possible, my philosophy has always been that long-term success means working at a sustainable pace. Anyone selling the Roof Maxx product learns the same lesson when they onboard so they can avoid learning it the hard way later.

Growing your business means learning to read the path ahead

Anytime you do something worthwhile, you’re going to face risks and challenges. That’s not a reason to quit; it’s a warning to prepare yourself for them.

You don’t go mountain biking without checking the pressure in your tires beforehand, packing a first-aid kit and sharing your itinerary with a friend so they can call for help if something unexpected occurs.

You don’t go into business selling a product like Roof Maxx without rigorously testing it first, training your dealers to sell and apply it properly and working with them to create mutually beneficial agreements. All of those steps help you proactively prevent problems down the road.

The Mohican State Park trail in Ohio is nearly 25 miles long. As the only trail in the entire state to hold an Epic designation from the International Mountain Bicycling Association (IMBA), it offers a true backcountry riding experience, with steep single-track trails that abruptly plunge into sweeping river valleys and densely wooded patches alike.

This is not a trail for casual riders. Completing such a trek requires more than enthusiasm; it requires strategy and instinct. You need to anticipate challenges before they appear in your path, conserve your energy for the most challenging stretches and allow yourself to rest and recover when you’ve earned it.

I grew up in Ohio, and I’ve ridden the Mohican State Park trail more times than I can count. I find myself thinking of it often, even when I’m nowhere near my mountain bike. In fact, some of the lessons it’s taught me about patience, stamina and willpower have been most valuable when I’ve faced challenges scaling my business.

On paper, our client looked like the ultimate win. They had scaled to 250 seats. They represented a substantial portion of our revenue, and the account was actively growing. By every traditional metric, this appeared to be a client worth celebrating.

But if you looked beyond the spreadsheet, they were a nightmare.

Every time this client’s name popped up on Slack or email, my team flinched. They would anxiously brace for impact. Instead of delivering proactive value, they found themselves constantly putting out fires. The client escalated every tiny hiccup into a major crisis, and my leadership team was spending hours untangling problems that should never have existed in the first place.

One day, an uncomfortable truth hit me. We were protecting the revenue, but it was coming at the expense of the culture we had carefully spent years building.

Here’s what I now know: getting a business to seven figures is largely about who you let in. Scaling to eight figures is more about who you’re willing to let go.

One thing nobody tells you when you’re building a business is that some businesses become less healthy as they grow. In the early stages, it’s easy to convince yourself that every paying client is a good client. Revenue feels validating, and saying yes feels like momentum.

That mindset fueled our initial growth. Eventually, however, I had to admit that some clients were costing us far more than they were paying us—not just financially, but operationally, emotionally and culturally.

The wrong-fit clients created constant urgency, distracted strong employees from important work, consumed leadership bandwidth and forced the company into reactive behavior instead of strategic growth. At first, I treated these situations as isolated problems. Eventually, I realized the pattern was the problem.

I wish I could say I immediately made the right decision. I didn’t.

Like most founders, I rationalized keeping them. I told myself the difficulties were temporary. I convinced myself the revenue mattered too much to walk away from. Most dangerously, I believed scaling meant learning how to tolerate more pressure.

But I was wrong. There is an important difference between pressure and misalignment.

Healthy growth inevitably creates pressure. Incompatibility creates drag.

Once I understood that distinction, we became much more intentional about who we worked with. That meant having uncomfortable conversations, exiting some accounts and turning down opportunities that would have looked exciting a year earlier.

In the short term, those decisions felt risky. Walking away from revenue is emotionally difficult when you remember how hard it was to generate it in the first place.

But almost immediately, the company became lighter. Communication improved. Managers had more space to think strategically. Team morale improved. The people who had been buried in reactive work suddenly had time to strengthen processes, solve bigger problems and deliver more value to the clients who were actually a fit.

Protect your team’s decision-making before you protect revenue

What surprised me most was that this wasn’t just affecting morale. It was affecting how my team actually thought and made decisions.

Yale neuroscientist Amy Arnsten has shown that under acute, uncontrollable stress, the brain floods the prefrontal cortex — the region responsible for judgment, planning and complex decisions — with norepinephrine and dopamine that rapidly weaken it while strengthening the more primitive, reactive responses run by the amygdala. Under prolonged stress, the prefrontal cortex physically atrophies. In other words, a chronically stressed employee isn’t just unhappy; they have measurably less access to the exact brain functions good work depends on. They become more reactive and less capable of thoughtful decision-making.

It would be impossible to eliminate stress, and not all stress is unhealthy. When there’s genuine danger, you want to be fast and reflexive rather than slow and deliberate. Time-bound pressure is part of why humans survive and build. The problem is the other kind of stress: the chronic, uncontrolled grind of a relationship that never resolves. That’s the buildup that ends in burnout. Gallup found burned-out employees are 2.6 times more likely to be actively job-hunting, and a Harvard Business School study put the turnover cost of a single toxic presence on a team at roughly $12,000.

Don’t mistake loss aversion for good leadership

If you catch yourself thinking, “But the client does add to revenue,” or “What if I let them go and regret it?” or “What if my good clients leave after I fire them?” that’s the flinch. It’s a normal fear response; most of us are wired for it.

The reframe that gets me past it is a single question:

How much freedom, and how much of my team’s capacity, could I redirect toward actually growing the company over the next 12 months if I let this client go today?

One caveat: don’t fire clients for being small. Small clients grow, refer and surprise you. Fire clients for being misaligned and draining. Size is a number; fit is a pattern. Don’t confuse the two.

Measure the hidden cost of every client relationship

Once you accept that some revenue is more expensive than it looks, you need a way to measure it. Mike Michalowicz, in The Pumpkin Plan, gave me a framework I keep returning to. He compares growing a business to growing a prize pumpkin. You don’t feed every vine equally. You identify the strongest growers, prune the rest and pour everything you have into the few that are actually thriving.

Translated to client work, the question is whether each client is profitable at the effort they actually require, and whether that profitability is trending up or down. Take a client’s revenue, divide it by the hours your team pours into them and compare that figure to the minimum hourly rate your business needs to clear. If they’re below your floor and the trend isn’t improving, you have a red flag.

This works whether you have three clients or three hundred because you’re measuring each client against your own cost floor rather than against your other clients. A high-demand client in a small book can still clear the bar easily, as long as the revenue justifies the effort.

If you don’t want to run the numbers, there’s a faster gut-check. When their name lights up your phone and your instinct is to brace, that’s usually the same answer the math would give you.

A client below the line today might be a fast grower or a critical referral engine. Always make the misaligned-versus-merely-small judgment before you make your move. But once you spot true misalignment, have the courage to cut the cord. Your path to eight figures depends on it.

The clients you keep shape the company you build. They influence your culture, your systems, your leadership team and, eventually, your growth ceiling.

Last year, I wrote about building a company through trust, loyalty, appreciation and proactiveness. This year, I learned something equally important: protecting those values sometimes requires letting the wrong people go. In many cases, that’s exactly what makes the next stage of growth possible.

On paper, our client looked like the ultimate win. They had scaled to 250 seats. They represented a substantial portion of our revenue, and the account was actively growing. By every traditional metric, this appeared to be a client worth celebrating.

But if you looked beyond the spreadsheet, they were a nightmare.

Every time this client’s name popped up on Slack or email, my team flinched. They would anxiously brace for impact. Instead of delivering proactive value, they found themselves constantly putting out fires. The client escalated every tiny hiccup into a major crisis, and my leadership team was spending hours untangling problems that should never have existed in the first place.

For years, the rule in text-to-speech has been simple. If you wanted the best-sounding voice for your product, you paid enterprise pricing. If you wanted cheap, you accepted robotic. If you wanted fast, you gave up something on both. That rule just broke.

The trade-off every product team has been forced to make

If you have ever built a voice agent, a phone system, or a real-time reader, you know the drill. You audition four or five models. One sounds incredible and costs more than your infrastructure. One is affordable and sounds like a GPS from 2009. One is fast, but only in three languages. You pick the least bad option and ship.

Then the invoice arrives.

And every quarter, your CFO asks the same question: why is voice the single most expensive line item in the stack?

What just changed on the leaderboards

This week, Speechify’s Simba 3.2 moved to first place on the Artificial Analysis text-to-speech leaderboard, ranking above ElevenLabs, Cartesia, OpenAI, and Google DeepMind. On Voice Arena, the blind-listener benchmark modeled on Chatbot Arena, it sits at the top for real-time models at its price point.

Neither leaderboard is run by Speechify. Neither uses self-reported scores. Native speakers hear two clips without knowing which model made which, and they vote for whichever sounds more natural.

Simba 3.2 is now the highest-rated real-time voice model a team can put in production today.

Here is where it gets uncomfortable for the incumbents.

The three numbers that matter

For anyone building with voice, only three things ever really mattered: quality, latency, and cost. Every model release has forced a compromise on at least one of them.

1. Quality. Simba 3.2 is ranked number one on Artificial Analysis and on top for quality and price on Voice Arena. Both benchmarks are independent. Both are blind.

2. Latency. It is a streaming-native model with lower time-to-first-byte than its predecessors, built for voice agents that respond in real time rather than after a pause that ruins the conversation. All sub-100ms. 

3. Cost. It is listed at $10 per one million characters, dropping to $6 per one million characters on the Scale tier. That makes it the cheapest model in the Artificial Analysis top ten, over fifteen times more affordable than ElevenLabs and roughly six times more affordable than Cartesia, according to the company.

Best-sounding, fastest, and cheapest have almost never described the same model. Now they do.

Credit: Speechify

Why this happened

The usual story with AI models is that the lab optimizes for the benchmark, prices for enterprise buyers, and lets the developer platform inherit whatever margin is left over. Speechify built it in the opposite order.

The same voice technology has been running inside a consumer product used by more than sixty million people for years. That audience does not tolerate a robotic voice, a two-second delay before the first word, or the kind of unit economics that only work at enterprise pricing. Every A/B test in that product fed back into the model.

“We made the architecture decisions at the beginning that most labs put off until later,” explained Raheel Kazi, an engineering leader at Speechify. “We never wanted to sacrifice on cost to chase quality, or sacrifice on quality to chase latency. We took the harder route on purpose. Hitting SOTA on all three at once is what that decision was always for.”

“This is the underdog story for API providers,” Luke Oliff, Head of Developer Relations at Speechify, said in a press release. “We spent years making our models run efficiently because our consumer business demanded it, tens of millions of listeners, with some of the best voices on the planet. That work is why we can now put the best-rated model in the world on our API at about as cheap as it comes. Most labs are built for the benchmark and priced for the enterprise. We built for listeners and priced for production.”

What Artificial Analysis and Voice Arena actually test

Neither leaderboard is the kind of benchmark a vendor can game.

Artificial Analysis runs on live serverless API endpoints, four times a day at random times, using a randomly selected voice, a unique 500-character prompt, and a standardized audio sample rate. Latency is measured end-to-end, all the way to when the audio file lands locally. 

Voice Arena uses the same blind pair-comparison principle across six languages, with a balanced voice slate per model rather than each vendor’s best-sounding default. The methodology was developed with input from Prof. Shinji Watanabe of Carnegie Mellon University.

On both boards, quality is scored the same way. Pairs of clips generated from identical text are played to native speakers in blind comparisons. Listeners choose which sounds more natural. Votes get aggregated into an Elo rating. No self-reported score, no vendor-selected clip, no internal panel, and no provider pays for inclusion or ranking.

For a model to sit near the top of both, it has to satisfy an objective performance evaluation and a blind human preference vote across multiple languages. Simba 3.2 does.

SpeechifyAI Agents and Speechify’s Developer Platform

Alongside the leaderboard result, Speechify is launching Voice Agents for businesses and a developer platform, both at speechify.ai. The model powering both is the same one running its consumer apps.

Simba 3.2 is a streaming-native model with low time-to-first-byte, fine-grained emotional control, and SSML prosody, engineered to sound natural in real-time voice applications. According to the company, more voices, additional languages, and an even lower-cost tier are already on the roadmap.

“Simba 3.2 is our best model yet, now available on Speechify.ai,” Cliff Weitzman, CEO and Founder of Speechify, shared in a public post. “It’s built to power voice agents at scale and perfected from millions of A/B tests we run in our consumer platform. In TTS APIs, three things matter: cost, quality, and latency. Simba 3.2 has achieved SOTA on this trifecta. Beyond excited for you to experience it firsthand to power your experiences.”

So is this the end of paying enterprise prices for voice?

For the teams that have already spent six figures on a voice bill this year, the answer is starting to look obvious.

For the teams that haven’t yet, the question is how long they are willing to keep paying for a trade-off that no longer exists.

Voice AI used to make you choose. It doesn’t anymore.

For years, the rule in text-to-speech has been simple. If you wanted the best-sounding voice for your product, you paid enterprise pricing. If you wanted cheap, you accepted robotic. If you wanted fast, you gave up something on both. That rule just broke.

The trade-off every product team has been forced to make

If you have ever built a voice agent, a phone system, or a real-time reader, you know the drill. You audition four or five models. One sounds incredible and costs more than your infrastructure. One is affordable and sounds like a GPS from 2009. One is fast, but only in three languages. You pick the least bad option and ship.

Then the invoice arrives.

Startup culture has, for years, promoted a narrow image of success: fast-moving founders, bold bets and the idea that you can figure things out as you go. That narrative is compelling and sometimes accurate, but it leaves out something far more predictive of long-term success: the value of experience in the room.

When you look at companies that actually scale and endure, one factor shows up consistently. It is not age, but applied experience. The real question is whether founders know how to use experience as an advantage.

The data tells a more useful story

The stereotype of the young, first-time founder persists, but the numbers point in a different direction. Here’s a stat that tends to shatter the way people think about startups: MIT notes that among “firms in the top 1/10 of the top 1%, in terms of growth, the average founder’s age is 45.” More importantly, founders with prior industry and operational experience are significantly more likely to build high-growth companies.

Young founders can, of course, succeed, but experience, whether it comes from past startups, operating roles or deep industry exposure, materially improves their odds. In practice, the strongest founding teams combine speed with judgment rather than relying on speed alone.

Clarity is what experience actually buys you

In early-stage companies, the biggest risk is often distraction. With too many opportunities and plausible paths forward, teams often spread themselves thin and lose momentum.

Experience sharpens prioritization. Leaders who have operated inside growing companies tend to make clearer decisions about what not to do because they have seen how quickly focus can drift and how difficult it is to regain. If you are building a company, make trade-offs explicit. Before adding a new initiative, decide what gets deprioritized. That discipline is what turns opportunity into progress.

Pattern recognition is a hidden form of speed

Startups pride themselves on moving quickly, but speed without pattern recognition often leads to repeated mistakes. Hiring the wrong leader, expanding too early or misreading demand are common problems across companies. Experience allows you to recognize these patterns earlier and respond with more confidence. Instead of solving every problem from scratch, experienced operators draw from prior outcomes.

You can build this capability internally by capturing lessons in real time. After key decisions such as hires, launches or pivots, document what worked and what did not. Over time, you create institutional experience even as a young company.

Discipline is what turns ideas into execution

Flexibility is valuable early on, but inconsistency quickly becomes a liability. Missed timelines, shifting priorities and unclear ownership are rarely strategic failures. They are execution breakdowns. Experience introduces structure where it matters. Leaders who have scaled teams understand how to create operating rhythms that support execution without slowing the business down.

For founders, this often comes down to a few fundamentals: stable weekly priorities, clear ownership and consistent check-ins focused on outcomes. Discipline protects your agility.

Resilience changes how decisions get made

Every startup faces volatility. The difference is how leaders interpret and respond to it. Without experience, it is easy to overreact by treating setbacks as crises or short-term wins as validation. Experience adds context. Leaders who have seen multiple cycles understand that progress is uneven, which allows them to stay focused and make more measured decisions.

One practical approach is to separate signal from noise. When something changes in your business, determine whether it reflects a real trend or a temporary event. Your response should match that distinction.

Experience matters most as you scale

The early stage rewards creativity and speed. Scaling rewards coordination and judgment. As companies grow, communication becomes more complex, decision-making slows and small misalignments compound. Many teams struggle simply because their operating model has not evolved.

Experience helps founders anticipate these shifts. It informs when to introduce process, how to structure teams and how to balance autonomy with alignment. The key is to design for scale before friction forces you to. Access to decades of experience creates a shortcut to hard-won answers. Why suffer through the headaches when you can find somebody who has already been down this road before?

Strong founders are deliberate about surrounding themselves with people who have seen what they have not, whether through co-founders, early hires or advisors. Waiting to figure it out later increases the cost of learning. Instead, identify where your experience gaps are today and address them early. That decision alone can accelerate your trajectory.

Expand the definition of a strong founder

This isn’t a choice between fresh thinking and experience — the best companies build both into the team from day one.

Take a medical software startup I work with. The founders are passionate, and the product works well, but none of them comes from a medical background. That gap could have been a liability. Instead, they moved quickly to bring in industry veterans as advisors — people who could kick the tires early and flag the hurdles before they became expensive mistakes.

The lesson scales beyond healthcare: if you don’t have the experience in-house, buy it. Bring on an advisor, hire an operator who’s scaled a similar business, or put a seasoned executive on your board before you need one. Waiting until a blind spot becomes a crisis is the expensive way to learn it. Founders who do this move fast without moving blindly. They still take risks — they just understand the trade-offs going in.

Startups will always celebrate speed and bold bets. But the companies built to last run on something quieter: better judgment, tighter discipline and a clear-eyed read of how businesses actually grow. If you want that edge, don’t wait to accumulate it yourself. Audit your team today for where your experience gaps are, and go find the people who’ve already closed them.

That is what experience brings into the room. In a market where everyone is moving fast, it may be the advantage that compounds the most over time.

Startup culture has, for years, promoted a narrow image of success: fast-moving founders, bold bets and the idea that you can figure things out as you go. That narrative is compelling and sometimes accurate, but it leaves out something far more predictive of long-term success: the value of experience in the room.

When you look at companies that actually scale and endure, one factor shows up consistently. It is not age, but applied experience. The real question is whether founders know how to use experience as an advantage.

The data tells a more useful story

The stereotype of the young, first-time founder persists, but the numbers point in a different direction. Here’s a stat that tends to shatter the way people think about startups: MIT notes that among “firms in the top 1/10 of the top 1%, in terms of growth, the average founder’s age is 45.” More importantly, founders with prior industry and operational experience are significantly more likely to build high-growth companies.