The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Startups & Founders/Building Billions with Brandon Dawson
Building Billions with Brandon Dawson artwork

S2 EP 27 Building Billions with JD Ross: Inside the Playbook Behind Multi-Billion Dollar Companies

Building Billions with Brandon Dawson · 2026-06-23 · 40 min

0:00--:--

Key moments - from our scoring

Substance score

59 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality11 / 20
Guest Caliber17 / 20
Specificity & Evidence10 / 20
Conversational Craft9 / 20

JD Ross built Opendoor from idea to $8 billion in revenue in under six years, taking the company public at age 30. He now leads With Coverage, reimagining insurance brokerage by replacing traditional brokers with AI-enabled risk management teams operating on transparent flat-fee models instead of hidden commissions. The episode covers Ross's core operating philosophy: the "rule of threes" (companies need structural rebuilding every time they triple in size), understanding your true business equation (inputs drive outputs), and the hard leadership truth that scaling beyond $3M requires shifting from being the hero to building a platform for others. Ross and host Brandon Dawson discuss the distinction between insurance (getting the right policy at the right price) and risk management (having expert advocates when claims happen). With Coverage aims to disrupt an industry reliant on opaque commission structures and fax machines by using AI to supercharge top talent and align incentives through flat fees - turning the broker's incentive from maximizing premiums to minimizing client costs. The conversation targets founders and operators scaling through the critical $3-100M growth phases where organizational design and understanding unit economics become survival factors.

Key takeaways

  • →Every time a company triples in size, the organizational structure and processes must be fundamentally rewritten - failure to apply this 'rule of threes' leads to bankruptcy.
  • →Scaling beyond $3M requires shifting from being the bottleneck (the 'do' person) to building a platform where you motivate, train, or replace people - not working harder yourself.
  • →Understanding your business equation (the true drivers and unit economics) gives you confidence to go unprofitable strategically; without it, you go bankrupt regardless of effort.
  • →With Coverage replaces commission-based insurance brokers with AI-supercharged expert teams on flat-fee models, aligning incentives to minimize client costs instead of maximizing premiums.
  • →Risk management (having expert advocates when claims occur) is fundamentally different from insurance (getting the right policy) - and claims management can return millions in recoveries that most business owners never access.

In this episode

  1. 1From Opendoor Founder to Building Billions: JD Ross's Journey
  2. 2The Rule of Threes: Scaling Companies Through Tripling Growth Stages
  3. 3Understanding Your Business Equation: Drivers, Profitability, and the $3M Wall
  4. 4Leadership and People: Motivate, Train, or Replace
  5. 5Atomic Ventures: Incubating Billion-Dollar Companies Like Hims
  6. 6With Coverage: Replacing Traditional Insurance Brokers with Risk Management
  7. 7From Insurance to Risk Management: Protecting Businesses from Career-Limiting Moments

Mentioned

JD RossOpendoorWith CoverageAtomic VenturesHims and HersFresh PrinceAddeparKeith RaboyEric WooAndrew DudumPeter ThielSquare

Guests

JD Ross

Topics in this episode

Risk managementtelemedicineOpendoorWith CoverageRule of threesBusiness unit economicsAtomic VenturesHims and HersInsurance brokerageCommission-based vs. flat-fee models

Questions this episode answers

What is the 'rule of threes' and why does every company need to follow it?

Every time a company triples in size, everything needs to be rewritten - from 2 founders to 3 leaders, then 9, then 27. By keeping revenue per employee and profit targets aligned while respecting this growth pattern, you maintain profitability; violating it leads to bankruptcy.

How did Opendoor grow from idea to $8 billion in revenue so quickly?

Ross founded Opendoor in late 2013 at age 23 with co-founders Keith Raboy and Eric Woo, working with Peter Thiel's original concept to offer fair-market cash for homes. The company scaled to $8 billion in revenue in under six years before going public in 2020.

What is the difference between insurance and risk management?

Insurance is securing the right policy at the right price with the right coverage; risk management is having expert attorneys and advocates available when claims occur to handle litigation, settlement strategy, and claims recovery - often returning millions in recoveries business owners never access.

Why do business owners get stuck at $3 million in revenue?

Most build the business around their own skills and become the hero; scaling beyond $3M requires turning yourself into a platform for others to succeed, which requires delegating the 'do' button and learning to motivate, train, or replace - something many resist due to loyalty or ego.

How does With Coverage change the insurance broker model?

Instead of traditional brokers taking hidden commissions, With Coverage uses AI to supercharge expert teams and operates on a transparent flat-fee model where their incentive is minimizing client costs, not maximizing premiums - creating aligned interests.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode contains several concrete operational insights - the Rule of Threes framework, understanding business drivers and equations, the transition from doing to leading (motivate/train/replace), and the shift from transactional to relationship-based business models. However, much of the content is conversational affirmation between two people who already agree, with significant portions dedicated to relationship-building and partnership announcements that add little novel substance. The core ideas are solid but not densely packed.

You need to know the drivers of your business, like what is the actual business equation? If you don't have a good grasp on that business equation, you are going to go bankrupt.
Every time a company triples in size, basically everything needs to be rewritten. That's the rule of threes.

Originality

11 / 20

While the Rule of Threes framework and the emphasis on win-win business models are useful, they are not particularly novel to experienced operators. The core thesis - that scaling requires understanding your business model, managing people effectively, and aligning incentives - is well-established in entrepreneurship literature. The With Coverage pitch itself is somewhat original (applying AI to insurance brokerage), but the episode largely recycles familiar scaling principles rather than offering contrarian or first-principles thinking.

The world is so full of win win opportunities. Everyone's always looking for transactions where they can get one on over someone. Those are really hard to find because you only get to play the game once with anyone.
It's not that they don't care like you do. Usually you have a skill problem.

Guest Caliber

17 / 20

JD Ross is a genuinely credible operator: founder of Opendoor (took public at $8B+ revenue in under 6 years starting at age 23), early employee at Addepar ($3-4B valuation), founder of Fresh Prince ($30M revenue), partner at Atomic Ventures, and now building With Coverage. He has real, scaled experience and meaningful exits/IPO experience. This is not a thought-leader or career podcaster; this is someone who has actually built and operated at significant scale multiple times.

I am the founder of Opendoor, which is a real estate technology company. We took public in 2020... We started the company and I was 23 years old... from the idea your first revenue to 8 billion in less than six years.
I've done a lot of early stage investing. My favorite time is the first thing I've learned to look at is the team... One of my very best investments I've ever made, a 50 X investment. I hated the idea and I loved the person.

Specificity & Evidence

10 / 20

The episode lacks concrete data, metrics, and examples to support claims. While JD mentions Opendoor's $8B revenue and age 23/30 milestones, With Coverage specifics are vague (no user counts, revenue, cost structure details). The HVAC case study mentioned by Brandon ("$16 million HVAC business" growing to "32 million with 7.8 million EBITDA") is mentioned but not explored. Most other claims (restaurants cutting hands, claims recovered) lack named examples or numbers. The conversation is illustrative rather than evidential.

We took public in 2020 and then joined Atomic Ventures as a partner. It's a firm behind Hims and hers and a number of other amazing companies.
This year it's probably going to be 2 or 3 times that next year in claims received that we've paid back to our clients from issues that came up.

Conversational Craft

9 / 20

Brandon Dawson is a friendly host but rarely challenges or probes deeply. When JD shares an insight, Brandon typically affirms and pivots to his own experience rather than asking clarifying follow-ups. There is minimal productive disagreement or pressure-testing. Questions tend to be open-ended setup rather than sharp investigations (e.g., 'Will you tell the audience what your next multibillion dollar play is right now?'). The conversation reads more like a mutual affirmation session between two successful operators building a partnership than an interrogation designed to extract maximum insight.

So will you tell the audience what your next multibillion dollar play is right now?
If you can't handle your shit in one conversation, you are not bankable. You are not bankable. [Brandon]: It's impossible. Impossible.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

million28insurance20team17billion15first15opportunity15three14businesses14different13back13idea12building11started11together11somebody11best11

Episode notes

In this episode of Building Billions , I sit down with JD Ross, founder of Opendoor, partner at Atomic Ventures, and founder of WithCoverage, to break down how he's taken companies from idea to billions in enterprise value, including scaling Opendoor from first revenue to an $8B public company in under six years. We get into what actually drives growth at scale, how to understand your business equation, why companies break as they expand, and what it really takes to build and lead teams beyond the founder, while also unpacking the massive opportunity in "boring" industries, AI-enabled operators, and the $5T+ small business wealth transfer that's reshaping where the next generation of billion-dollar companies will be built. Support the show: See omnystudio.com/listener for privacy information.

Full transcript

40 min

Transcribed and scored by The B2B Podcast Index.

WEBVTT - S2 EP 27 Building Billions with JD Ross: Inside the Playbook Behind Multi-Billion Dollar Companies Welcome to Building Billions. Building a 10 million, 100 million, billion or multi-billion dollar business is actually based on three things consistency, velocity, and results. I built, scaled and exited and rebuilt many businesses in my career. If you're serious about creating something that has real enterprise value, stay tuned.

This is building billions with Brandon Dawson. I am the founder of With Coverage, a modern replacement for your insurance broker previously, I'm the founder of Opendoor, which is a real estate technology company. We took public in 2020. And you went from the idea your first revenue to 8 billion.

Yeah, this is less than six years later. Six years. Yeah. Unbelievable.

We started the company and I was 23 years old. 23 yeah, I think the world is so full of win win opportunities. Everyone's always looking for transactions where they can get one on over someone. Those are really hard to find because you only get to play the game once with anyone.

When you win win together, you get to keep playing. You need to know the drivers of your business, like what is the actual business equation? If you don't have a good grasp on that business equation, you are going to go bankrupt. And if you can't handle your shit in one conversation, you are not bankable.

You are not bankable. It's impossible. Impossible. They've spent their whole career building this company, and then in one moment, they get one phone call and it could all be taken from them.

One wrong conversation. You can lose it all. And so our team acts as your advocate and support team so you can survive. Stay tuned because when you see what we actually do together, you're going to be mind blown.

Will you tell the audience what your next multibillion dollar play is right now? JD welcome to my show, Building Billions with Brandon Dawson. And I love shooting content with people I admire. I respect that are successful, especially younger entrepreneurs.

And the title of this show couldn't be better represented based on the things that you've done. So will you introduce yourself to my audience, talk a little bit about who you are and some of the things that you've done. Sure. My name is JD Ross.

I am the current founder of With coverage, a modern replacement for your insurance broker. Previously, I'm the founder of Opendoor, which is a real estate technology company. We took public in 2020 and then joined Atomic Ventures as a partner. It's a firm behind Hims and hers and a number of other amazing companies.

And today, trying to just fix the insurance industry. So it's suffice to say you just blew through that open door. Oh, yeah. I'm the founder of Open Door.

Yeah. So Open Door, when you founded it, what year did you found it? We started the company in 20. At the very end of 2013.

I was 23 years old. 23. Yeah. And that was your first company you founded?

Uh, no, I had started a couple companies in college. One was called, uh, Fresh Prince that does about 30 million a year in sales this year. Does custom apparel on college campuses. Started that when I was 18.

And then I was the one of the on the founding team of a firm called Addepar, which is a wealth management, uh, software, basically, technology helps people understand what they actually own, uh, helps banks understand what they actually own. And that company is valued, I think, between 3 and $4 billion. Okay. So then you go start Opendoor.

You had an idea? Yeah. What gave you the idea? So I'd been friends with Keith Raboy, who was a famous operator in Silicon Valley.

He was the chief operating officer of square. He was part of what they call the PayPal mafia, the people who started PayPal and then built these incredible businesses. And Keith and I have been talking for years about what we could do together in all kinds of ways. And he had wanted to do this idea with Peter Thiel called homerun, and he was like, what if we just have someone enter their address and we just they tell us what they want to sell for and we just say yes or no.

I was like, there's something really interesting there, but that's a terrible idea. Um, but if we switch it and we tell them what we think their home is worth and show them why, and then we can make them an offer, then I think there's actually the opportunity here to we call bring liquidity, allow people to get cash for their home in a way that's fair at a full market price. I think we can do that and really win. And so our story was just like, there's got to be a way to make real estate change.

It's been the same for 100 years. And we had. And Keith finally introduced me to Eric Woo, who is my co-founder. And the three of us came together and then brought on our fourth co-founder, Ian, and it was just off to the races.

So how when did you exit Open Door? I left the business just before the IPO happened. We'd already kind of gone through the process and talking about what we were going to do. I left, uh, partly because I think in each stage of your career, I think you optimize for different things.

At that point, what was clear to me was the company had grown. We were something like 1500, 2000 people, 8 billion in revenue. Wow, wow. So literally, you had an idea, you took action.

And over what period of time you went from the idea, your first revenue to 8 billion? Yeah. This is like less than six years later. Six years.

Yeah. Unbelievable. It was a crazy run we hired. And that was before 30 years old.

Yeah. Yeah. That's right. We, um.

Yeah, I was 30 years old when the company finally went public. I just turned 30. I think what was interesting about that experience is that you learn all the ways that companies break as they scale. I now have this thing called rule of threes.

Every time a company triples in size, basically everything needs to be rewritten. That's funny because every rule I have is the rule of three. It's more seamless when I hear you say that, because when you first start your business, it's going to boil down to the two people you bring with you. Yep.

Can you get to a million? Then if that works, by the time you go from 8 to 15 million, the new rule of three is you got there has to be three leaders in that company because you've added more people and then it compounds. So it's locations or people. It goes from 1 to 3, three times three, nine, nine times three, 27.

And if you just stick to that theme, but you keep your revenue per employee and your profit targets per revenue in line, you'll never have a business that's falling out of profitability or success, but you break and violate those rules. You go bankrupt. Yeah. You need to know the We call it the the drivers of your business.

Like what is the actual business equation? If you don't know the inputs, your outputs are totally random. And so you need to get a really early grasp on what actually drives the business. And by the way, if you know what drives your business so well, you can go unprofitable.

You can choose to raise money and go unprofitable because you know when it's going to come back around, you can have the confidence to grow faster. If you don't have a good grasp on that business equation, you are going to go bankrupt. Well, and I think this is the thing between a really successful entrepreneur and a one and done versus 97% of business owners that drift or go out of business. Once you understand what the algorithm is and you understand what the trade offs are.

And I think that's the thing. Most business owners grow their business to about 3 million, and then they sit and then they decline in profitability and then or they push through, get bigger decline in profitability until they can't grow anymore. And then they shrink or they go out of business. Unfortunately, then you can you have the confidence to be like, all right, well, I'll forward invest to get more velocity.

And if the indicators start to warn you, reverse down to where you can break it even or make. But you know, you can feel it, you know. I think what happens to a lot of people when they get to that $3 million mark you're talking about, is that they've built this business around their own skills. They're the hero of the story, and they've built people to compliment them, but it's still actually about them at the end of the day, to get from that three to that ten to that 30 to that hundred to that billion dollars of revenue.

It's no longer about you. It's about taking what you learned and turning you into a platform for other people to succeed. And I think people get really caught up on why can't I scale? I'm already working 80, 90 hour weeks.

I have my customers, I have my model, my product. People are letting me down. They don't care like I do. Exactly.

It's not that they don't care like they like you do. And maybe it is, by the way, if they don't care like you do, you gotta. You gotta. Have a motivation problem.

But usually you have a skill problem. I think actually when I'm talking to new managers, I say, look, you no longer have the do button. You've been hitting the do button all the time. You're very good at hitting the do button.

Now you're in charge of people. Now you have two options. You have motivate train and you have a third option replace. That's all you can do.

You can motivate if they can do it, but they're not doing it like you're going to hang $1 million in front of them and they could get it done. That's a motivation problem. You got to motivate. If they can't do it, you've got a training problem.

That's where you need to say, okay, what is the scope of your job? Are you even capable of developing into that. Despite if they're your friend or they've been with you or they've been there from the beginning, at some point, if the business requirements have exceeded the skill set or desire of the individual to advance in their ability to deliver or personally invest in their growth, and you're the leader of that company, what then decision do you have if they're unwilling to scale with the business?

Yeah. Your decision is either to layer or replace them or to stagnate. Those are only two choices. Or decline.

You can't sit there with someone who's holding back your company out of loyalty and realize you're not being disloyal to everyone else in the organization and yourself for the opportunity you're holding back. So much wisdom in that statement, because a lot of people have friends from college, extended family in the business. They tend to let them do whatever they're going to do, and they tend to get mad at the people that are trying to win. And if you're in that environment in a small business and you're like, I'm going to go somewhere else.

At any given point in time, a company is pandering to someone's ego. And surprisingly often I see business owners and entrepreneurs pandering to the egos of the employees who they were there with, not even to their own ego because they think they're being selfless, but actually they're just pandering to a different ego. Mhm. That's a good that is good.

That's what insight from a multibillion dollar operator, because, you know, you don't get that big if you're not going through a lot of people to have 2000 people at Open Door, you've probably gone through 5000 to land it too. By the time it's all said and done. I think of the first, and this is common in lots of businesses. When you're starting off of the first, maybe ten people you bring on, maybe you might let go of four, it might four might not work out.

And of the next 25, maybe four don't work out. And the next hundred, maybe four don't work out because you're learning what kind of person thrives in your environment. But you have to be able to understand that like just because someone doesn't do a great job in this role in this business, they're not going to be incredible elsewhere. They might be unbelievable for another business.

It could be a DNA mismatch. It could be all kinds of things. But you have to let them free for yourself, for your business, for your other employees. Say that again, because I think it's important when people think, oh, I can't fire somebody or I can't get rid of somebody, but as an experienced operator, because I can tell by the language you're using, we think exactly the same.

You didn't say, you have to fire him. You said what? You have to let them move on. You have to let them free.

You have to let them free them up. Go do something you are excited about. Go find life. And if you can't find it here, no harm, no foul.

There's a really. I always thought this was so funny because it was such a good euphemism. In college, the sororities had this phrase shine better elsewhere. And it was, uh.

I always thought that was hilarious, but it is. The irony, of course, is now that I'm older, it's true. Like, just because you are not fit for somewhere does not mean you are not a fit. You have.

The world is enormous. Everyone is individually spectacular in their own way. They just need to find that home. Yep.

And some people get lost along the way and don't know what they want. And then they blame the environment they're in. Yeah, but you're also in control of your environment. You can leave your like there's.

Isn't that amazing for people that complain about where they're at? Personal life, professional life, financial life. And they don't acknowledge the fact that I'm actually in control. Of my life.

You're alive. Yeah. Or you can choose to be alive. I think a lot of people choose the easiest path, which is to basically minimally be alive.

But the options are always there to take control. And I think this is the beauty of, I think being in being a raised, at least from an entrepreneurial sense in Silicon Valley is it's a very high agency place. Everyone themselves individually thinks that they have the ability to change the future whether they do or don't. But it's a very inspiring place to kind of grow up.

Yeah. Because they see so many other people doing it. So now you get this kind of effect, this magnetism effect. Talk a little bit about so you built Opendoor $8 billion.

Unbelievable. Then what did you you started at? What did you say? Atomic.

Atomic ventures. Yeah. So what was. It like getting to make the move to Atomic Ventures where you got to see all these?

Because Hims is a multibillion dollar company, and you get to see founders like you that you get to help. Yeah. And choose to invest in. And you get to vicariously live through that success to talk about the difference between you in the heater and you guiding, advising and investing in somebody else that stepped into the heater.

I think what was really interesting about being at atomic, which I think was halfway between being a pure VC and being an entrepreneur, right? Because you're incubating companies. We were bringing founders together, founding teams. We were helping them get them off the ground.

And Hims was started by Andrew Dudum, who was the CEO of that company at atomic. He was a partner at atomic. And so he really took the reins from day one. And why.

Did he pick that. Business? I think they saw the opportunity with telemedicine. There's two things that happened at the same time.

One is that viagra went off patent. Very important for that business to get it off the ground. And two was that telemedicine, the infrastructure to enable people to kind of talk to a doctor at home through their phone, was just starting to work. And they took those two things together and kicked it off.

And now that's not even, you know, that's a small part of their business today. Yep. So you got to see that somebody had an idea. Yep.

I think the best ideas, and I think I heard you say it from stage. So I know that we're aligned in. This is when you can insert yourself in an already existing ecosystem, organize it a little better to create more wins for the people that need those wins, which creates velocity, which then gives you control. And so in this particular case, the new thing you've moved to, which I am, I've been tracking this for ten years.

I'm an investor in two companies that have tried to do this at a different level. And as soon as I met you and you talked about what you're doing, I'm like, I know exactly what that opportunity looks like. So will you tell the audience what your next multibillion dollar play is right now? Yeah.

So right now we started a company called With coverage. And what we do is we replace the traditional insurance broker with a modern risk management team and platform. What I mean by that is today your insurance broker probably plays golf with you if you're a big enough company, but they're not really deeply understanding the risk of your business, and they're not proactively trying to monitor this. And they're charging you secret commissions that you don't even know about.

You have no idea what they're being paid. And so what we do is to say, okay, a couple of things. First of all, AI is here. And what AI does, people think AI replaces employees or whatever.

That's not what we do. AI supercharges our team to make every single one of them the best insurance broker on earth. And so you have this team of excellent people that we've recruited from all the top brokers who are absolutely phenomenal at one thing by vertical. They're the best home services roofing, Hvac person, the best consumer brands person.

They might even in our case, one of our technology people helped write the forms for cybersecurity. He helped invent cybersecurity. And so what we do then is we pair those people with the platform so that they can go in and really understand your business, what your risks are, help you see around corners and then save you money. And so we'll go to the full market 2050 carriers, make them all compete for your business, drive savings every single year, and push that back into your business with less time from you and from us.

Which I know for a fact because I'm an investor and a technology eight years ago, and it's been clunking along where it was trying to aggregate a single source of truth collection process and then disperse that across all the carriers. So you could break out all the line items of different insurances for different reasons. Get a macro quote from everybody on each line item versus a blanket insurance quote, and then pick the best of the lowest expense with the highest value. And then go give that bid to your client to do exactly what you're doing.

And the complexity in that, because these insurance companies use fax machine, they do every they're like the health care reimbursement companies. They do everything they can to keep the end point distribution person, the person that you actually trust as blind and dumb as possible by making it as difficult as possible to actually understand how to find those little hidden opportunities to save you money. Because they don't want you shopping around. They want to be the only one you're going to, so that they can put out whatever bid that they need to, to win.

And the broker in the middle, it's not that they're bad people, it's just they don't have the bandwidth, skill set or ability to, quote 30, 40 carriers. They're not gonna go. To the one they're most comfortable with, with the paperwork they're most used to using. And.

Maybe the highest commission paid to them, you know? Yeah. It's all these things. And I think for us, what we've done is once people are spending enough money on insurance to care about it, we move them from a commission model to a flat fee model where now where our incentives are aligned.

So upfront, you know, you're saving money. Last year you spent $20,000 in commissions. We'll show that to you. This year, our flat fee is $15,000.

You're spending $250,000 in commissions. We're going to charge you $150,000. You know you're going to save $100,000 right off the bat. Then we're aligned.

Incentive. Our job is to drive your cost as low as possible, not as high as possible. Like the last guy. Yep.

Totally different way of thinking about it. And because we use technology, our cost to serve is much lower. And the speed, because I have clients, you know, we talk about home services, but in every field that have had what I would refer to as career limiting, devastating moments. Yeah.

And something as dumb as an employee disconnecting the backup sensor on a commercial truck, something as dumb as disconnecting the front camera of a truck. Something as simple as not following safety protocols for a roofing or construction company. To a lawyer, having an employee not use proper communication channels and divulging confidential information like, you know, health care companies not being HIPAA compliant because they're taking shortcuts. So when you when you look at all the little moving parts of a business, it, it becomes normal for them.

And then until they get caught or something bad happens, and then they're devastated from it because they didn't know they were doing it. They spent their whole career building this company, and then in one moment, they get one phone call and it could all be taken from them, and they don't know why, and they don't know what they were supposed to do. It's 100%. And it could be something as simple as getting that letter saying, your website's not 80.

What is it. Ada compliant. Ada compliant, and next thing you know, you have a class action lawsuit and some lawyer trying to get 5000 grand out of you and you're like, that's the last money I have to an employee doing something and turning you into the city because you didn't have proper authority or opportunity to do it. Right.

Right. And this, by the way, is where we come in. And this this to me is the difference between insurance and risk management. Yep.

Okay, so let's talk about that. Yeah. Insurance is we're going to go out and get you the policy paper you need at the price you need with the coverage you need. Risk management is when something goes wrong, who do you call?

We have a team of attorneys who are there who are there to make sure that when something goes wrong, you are taken care of. So when someone does do that backup sensor thing and they back up the truck and someone gets hit and you get sued for millions of dollars, what are you supposed to do? Are you supposed to settle? Are you supposed to talk to your insurance carrier?

What's the playbook? This is all new to you. You're in the business of your business. You're not in the business of managing this kind of stuff.

Yep. And one wrong conversation. You can lose it all. And you can lose it all.

And so our team acts as your advocate and support team in pushing that story forward. So you can survive. So you can move forward. You can be fully.

Well, you at least know what the absolute on average, best outcomes could be. Instead of freaking out that it's going to be the worst case scenario. Right. And everything you're on your own, you're probably going to end up with the worst case scenario.

Because you don't know this is not what you were put on the planet to do. This was not your game. We do this every day. We've brought on tens of millions of dollars back to our clients.

This year. It's probably going to be 2 or 3 times that next year in, uh, claims received that we've paid back to them from issues that came up. Now, because you have this mentality of, how do I insert myself into a marketplace that I can add value to, to hyper scale that value and make it a win win for everybody, but maybe the insurance company, but for the insurance companies that get the business, it's a win. Yeah, they're thrilled with us.

We're some of the fastest growing businesses they've ever had, but that's also because we bring great clients to them. Yeah. Because again, risk management is not just insurance. We're going through all their historical claims and we're saying, hey, did you know that in your restaurant group, 20 people cut their hands last year?

Maybe you should put cutting gloves on. We're going to show you how to establish a policy. We're going to help you establish a new policy that's going to save you $100,000 a year. And so it's not just the insurance companies that are like, this is fantastic.

You've saved us $100,000 a year. And everybody wins there. Yeah, I think the world is so full of win win opportunities. Everyone's always looking for transactions where they can get one on over someone.

First of all, those are really hard to find because you only get to play the game once with anyone. When you win win together, you get to keep playing. So you get to just keep stacking wins through your whole life. If you're doing things where you're in collaboration instead of competition.

Just very important because I know you well enough to know, and I think when you get to a certain level of success, you kind of start to realize how to view the world. And I always talk about that micro percent of really successful entrepreneurs, we all tend to talk around very similarly the same things, and we recognize each other's language. What you just said is critically important, that the average business owner doesn't stop before they start a business. And think about what you just said is when you can go and create a business, that's a win win.

It goes on forever and it gets bigger because it compounds when you create a transactional business. Well, when we did all of our studies, we found that after 60 months of being in business, if your revenue didn't shift from 80% new customers, 20% something you're selling somebody you already had a relationship with to 65% selling something to somebody you built the relationship with in the first 60 months, 35% new, dropping your promotion down from 1,820% down to 6 to 8. Long term, you go out of business because you're purely transactional and you can't scale something that's just a one time transactional business you're starting.

It's the same as starting your business from scratch every single month. It's like, great, I'm glad we did all this hard work. Everyone. Guess what?

Business is now back at zero. You can do it again. Let's do it again. You can maybe stay alive that way with enough sheer force of will, but you're never going to become a big business.

No. And talk a little bit. You've seen these exits. You've seen these IPOs.

You've seen things go from being worth 1 or 2 times profitability or EBITDA and then going public at 20, 30, 40 or being bought at 50 or whatever, like it's when you have. So talk a little bit about, from your perspective, a builder, a multibillion dollar companies and an investor into companies that became multi-billion dollar companies. When you're looking at that thesis, what are the top three things you look at to know? Could it be a good investment?

Should we go all in on it or should we walk away from it? I do a lot of early stage investing. It's my favorite time, and the first thing I've learned to look at is the is the team. Yep.

Like the not even the opportunity at that point. The problem with looking at the opportunity is I started thinking about the opportunity on how I would run that business. I'm not running that business. That's right.

So even if I'm right, very good. Even if I'm right, it doesn't matter. So first is the team. And by the way, one of my very best investments I've ever made, a 50 X investment.

I hated the idea and I loved the person. And it turns out three months later, he hated the idea and he changed it. And now it's $1 billion company as of last month. Wow.

I mean, this is why I mean, I, you know, I think people should hear this. They all go pitch their stupid ass ideas, and while they're pitching it, they get mad when somebody doesn't see their vision. They get bitchy. They get.

They get droopy, they get short. And what they don't understand in that moment is they're being tested to see how much they can actually carry, because any investor knows that to actually build the thing they're talking about, you're going to go through a myriad of multiplied emotions to make it work. And if you can't handle your shit in one conversation, you are not bankable. You are not bankable.

It's impossible. Impossible. Because guess what? If you do succeed, now you've got 100 employees, 200 employees.

It's all hands. You're in front of the room and you've had your your favorite employee just told you they were leaving. The new hire you just made didn't work out. Your favorite customer says, sorry, I love you, but we've outgrown you.

And then you have to get on stage. And guess what? Everyone in the room doesn't care about any of that. They couldn't care less.

They just need to know that you're there and you're confident. So you need to be able to separate out everything you're feeling. Put that aside and show up. And that's that.

I call it the entrepreneurial dilemma because you started your business. If you look at when we did our surveys back in nine, ten, 11, and 12, all these thousands of business owners, and we asked, why did you start your business? And here was the answer of and I'm talking about all businesses under 100 million. So 1 million, 100,000 to 100 million.

I didn't want a boss. I didn't want to be told what to do. I didn't want to be held accountable. I didn't want a limitation on my earnings.

And I wanted to do my own thing. That's why they started it. Now, if they're actually good at the thing they do, they got to hire people. And the entrepreneurial dilemma is people are going to be like me.

Yeah. And now I gotta because if you read every employee engagement survey, employees want to be led, developed, nurtured, inspired and paid well. And they want an idea of what the career opportunity. It's entirely different than how the founder thinks completely.

And then that's where everything falls down, because they can never figure out what's wrong with people. What's wrong with people, honestly, is they're not lunatics like you, or. They would be doing what you're doing. And by the way, the people you bring on who are entrepreneurs at heart, they're coming on to learn from you.

They're going to be there for one, two, three years maybe before they leave and do it themselves. Unless you have a big enough vision that they can stay inside your bubble with you. Yeah, at a certain scale and size. That's true.

And you talk a little bit about when you find people you need today, because look, you have the legacy, you have the experience. And this is what I think a lot of people don't understand is you don't have to try to go build a $100 million company over 30 years. If you get great at going from 3 to 10, 3 to 10, 3 to 10, 3 to 10, and you get good at understanding value, selling the ten for for 8 to 12, and you do it ten times. Then when you go to somebody who's working in a million and a half dollar business said, do you want to go on the ride with me to 10 million.

Sell it for 15 or 12 million and I'll pay you a million. People are like, how many times can we do that? We can do it 20 times. You're going to get a different attention from somebody now at your level when you're like, hey, you know, 8 billion, 10 billion.

4 billion, 6 billion. When you go up to somebody and say, hey, you want to come alongside. And if you do all the things you need to do, you develop at the level you need to develop, you contribute consistently, consistently at the level you need to contribute, and you grow personally, professionally and financially to be the example on behalf of everybody else in the organization, you could have a shot at being worth 3 to 10 million with me. Oh, absolutely.

One of those conversations sound like when you're talking to those people. I think there's there's so many different archetypes of people, right? Some people are thrilled by that. Some people are like, I'm going to start a $100 million company.

So that first 3 million I'm going to make with you is going to be just the, the training grounds for who I'm going to be. And I love those people. I want as many of those people. My company might be your future partner.

I can't wait to invest in them after they leave. I can't wait to buy a business and let them have 80%. You have 20. Totally.

All these like there's a million opportunities for people. But I think what we try to do when we're built, and the reason I think that it's so important to go for the biggest vision you can, is that the bigger vision attracts the best people, because the best people are the ones who say, okay, I see that I'm spiky. I'm not like you, JD. I'm not across all these different things.

I'm not total chaos. I'm really dang good at this. I'm like, great, I'm going to make you the most empowered, the most developed, the most successful X ever. If we can work together and I need to have that opportunity, the opportunity has to be big enough for that to be true, or else they'll smell it quickly and move on.

Yeah. And if you have no credibility or you don't do the things necessary to show them you're actually serious about it, why would they stay in. The loop of my loop at this point is basically Foreshadow and deliver with the team. I'm going to foreshadow exactly what's going to happen over the next three months, six months, nine months, and then we're going to deliver that.

And if we don't, the loop breaks. And when the loop breaks, it's hard. Now all of a sudden we have to recalibrate the whole team. But when that loop is solid, smooth sailing, things move really nice.

So, you know, you and I were entering this partnership to bring all this value between our different organizations to 36 million small to midsize business owners. And I know for a fact it's going to be massively impactful for them. But I also know it's not just about the money they're going to save and the better value they're going to get. It will be the thing that keeps a lot of them in business because they don't know what they don't know.

And it's usually this one area compliance or, or lack of having proper insurance that just overnight wipes them out. Right? So to be able to partner and bring that from a security standpoint with someone that's known, like trusted is going to be a huge value to these 36 million business owners. Talk a little bit about what the process is for them to know.

Can we help them? Yeah, I think today there are insurance companies that do a great job. I think for the very small business, it's online, you can fill it out. They're not really looking into the risk for you because you don't have enough risk to need to play defense.

Once you're at a place where you're as a founder, an entrepreneur, you're always playing offense. You're in the game of offense, right? You can't you don't have time to think about defense. And so it gets left aside until something bad happens.

Once you're an entrepreneur who's paying, I don't know, $100,000 a year in insurance. Defense matters not just in terms of cost optimization and service, but also knowing that you're covered for the things that really matter, that risk management piece. And so what we do is we come in and say, we're going to be your new risk management team. It's time for you to level up.

And we're here to help you level up. And we're going to make it as easy as possible. We're going to prefill all your forms in PDFs. We're going to use AI to do all this back office work.

You don't need to worry about. We're going to find the holes that you don't even know exists. We're going to do a free. We're going to start the relationship.

By the way, we're not starting the relationship with, hey, work with us. We're going to start the relationship with. We're going to do a free in-depth risk analysis. We're going to go policy by policy, show you every gap error, omission, missed benchmark price.

Here's what we're going to do. We're going to foreshadow and then we're going to deliver. Same thing I do in my team. We're going to do what we do for our clients.

And that's free. And all of a sudden, you know, no harm, no foul or whoa, I could save a lot of money or increase significant amount of protection that I don't know, I need that I don't currently have. Yeah. For that rainy day where we come in and by the way, one in 10 to 20 times, we'll go back to someone and say, hey, your program is crystal clear.

You're in a great spot. No changes, nothing. If you like our platform, which is a great digital platform, make your life easier. Come switch over.

But we're not going to change very much here. The other times you've probably been with the same insurance broker for four or 5 or 10 years. They haven't looked at it. They're not shopping it.

Tons of opportunity. They're just doing price increases every year. Yeah, because they know you're never gonna. Leave and they're getting paid their commission.

So it's all recurring revenue for them. Everybody's happy. Oh, you like golfing? I love golfing.

Golf. Let's go play golf for your golf. Yeah you are. Yeah.

And so we are we're a different approach to the problem. Yeah. Well I know for a fact. I mean, let me ask you this.

And then we're going to have to we're going to have to end this and pick it up another time. But let me ask you this. You've seen a lot of things in your life. This is your first experience actually in our environment with 500 entrepreneurs who all have nice businesses.

Have you ever experienced what you saw in the first three hours this morning? Any company that's bringing this kind of value to those small businesses. I've never seen anything. What you have done is incredible.

You. You've built a playbook to grow the. There's the local entrepreneur who's been building with maybe they have a couple local mentors. You're like, no, no, no, here's not just how to think bigger, here's how to be bigger.

And you take them there. You've broken it down to to a science. You took this art into a science. And it's amazing just hearing the stories of so many of these businesses that you've worked with and how they've gone from 3 to 7 to 10 to 27 plus million dollars in just a few short years.

It's amazing. And when you think about the untapped as a business person and investor, when you sit here and look at the this whole thing that I've spent the last 25 years creating and now with, with Trump signing the Genius Act and the Clarity Act. And then I talked to you a little bit about my strategy of bypassing Wall Street and going and putting $1 trillion of the $16 trillion marketplace and creating our own version of Wall Street, allowing Main Street to invest in friends, family, successful businesses, access to these businesses under the new laws, new rules digitally available.

When you heard me talk about that and you think about that opportunity as someone who thinks in the billions, what do you think is the probability knowing the the research Sequoia just put out, knowing the combination of P groups trying to create consultative companies with AI, seeing this $16 trillion non-organized non configured space. And you see, though the difference between us thinking about it is we're actually have built the system for 20 years and we're doing it. I think if anyone's going to be able to take Main Street and help them grow like Wall Street, it's you with what you're doing because you're not just for you.

It's not a one one time thing. You've done this ten, 20, 100 times now with these different companies and you're coming in and saying, hey, the reason you're held back is because you just don't have the information in the system. We have the information, we have the system now, you just have to execute it. Yep.

So it goes from being on. They can blame anything. Now the only person they have to blame is going to be themselves. And some people will find ways to blame other people.

But if you can do that over and over again, you can create. It's not going to be one of the trillion. It's going to be ten of the trillion. Yeah.

Because they're all going to grow so quickly. Well, when you combine that capable entrepreneur operating on a proven system and track record, who has the internal motivation because they're winning with their team based on how we've structured it, with the fact that there's 5 trillion of their peers that are entering the silver tsunami with no exit strategy, with businesses that are worth very little. We took a $16 million Hvac business that every year it grew. It was lowering its profitability down to 400 grand.

And we just restructured, reconfigured. And 15 months later, we did 32 million with 7.8 million of EBITDA and no debt. How did we do it?

Well, we picked off strategically six $1.2 million exiting silver tsunami ers with their teams that have been underserved for five years because those business owners gave up. We wrote checks for 100,150 grand. We picked up 4 or 5 vans, 8 or 9 employees, and then overlaid the promotion on top of it and interlaid the operational effectiveness and put them on our system.

And all of a sudden explosion happens and people are full of energy and new opportunities arise. You're a master at building businesses. I'm I believe I've spent my career to become a master at organizing businesses and creating life inside that business for the people who are actually doing the work. That's where I deviate a little bit from traditional P.

E. because that was my first big investor. It's like push, push, push, push, but not a lot of help because none of these educated people that write checks actually know how to go into a $3 million business. Because it's people, it's to it's they, they don't they, they think in terms of spreadsheets.

That's right. These are people and you know how to work with people. And they need. And when a p e group or a venture group or a public company group, investors see that somebody can relate to those people, inspire them to find that internal motivation, align their team.

They all know the marketplace is there. Yeah. They know all the revenues there. It's just so fragmented and disorganized and discombobulated.

And so if if we can smash because the thing I'm going to ask you to do, well, we're building the with coverage ten X coverage together, I'm going to ask you to help me bring those relationships. You have the Wall Street relationships, those successful people, because I, I decided not to take Wall Street money back in 2002 when I didn't do it right with Warburg. And even though if I was them at that time, I would have sold my company to knowing how I was. But the view today is the biggest untapped opportunity.

The next trillion plus is in two verticals that I'm heavily vested in right now. One is the health vertical with human optimization and performance and longevity, and the other is bringing together trillions of dollars of small business owners so they can have legacy impact with their family, their friends, and their employees. And those two I see as the biggest opportunities I've ever been in the center of. And I'm going to need help with smart people who love to win like you.

Yeah, I think it's just showing them everyone right now is so interested in the private equity angle of how private equity can buy out all these small businesses and roll them up and turn them into probably this ghost shell of themselves. You're taking the opposite approach. You're saying, actually, let's take the operating system of the best and give that to the owner so that they can lift themselves up. I think it's more not only is it more compelling, I just believe bottoms up beats tops down every day.

I think that's how the economy works. I think that's how human happiness works. Like everything is like that. So I think you have the right playbook.

Awesome. Well, we're going to get a chance to be a part of each other's playbook. So JD, I know we're going to put a lot of other content out. I'm so excited to build this with you.

So excited. The impact for all the people we get to work with and serve and improve their opportunity in business and in life, personally and professionally, all that stuff. I'm so this is what I love to do and I love to do it with successful, smart people. One of the best things in my career.

I get to meet those people and figure out a way to work with them. So for me to you. Thank you for joining me on building Billy and sharing your story and everyone watching or listening to this episode. Stay tuned.

Because when you see what we actually do together, you're going to be mind blown. I'm grateful for the partnership and the friendship. It's going to be amazing. Thanks, brother.

Thank you.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Corporate Finance Explained | When Bitcoin Hits The Balance SheetFinPod · on Risk management80 / 100
  • Navigating AI Risks with Trevor Horwitz from TrustNetB2B Automation Spotlight · on Risk management79 / 100
  • The Financial Stakes of Risk Management in a Self-Insured CaptiveThe Canary Report: Safety & Risk Management · on Risk management77 / 100
  • 111: CPM in the Insurance Industry with OneStreamOneStream CPM Customer Success · on Insurance brokerage37 / 100
  • How Vertical SaaS Solves the Compliance Trap in ConstructionVertical SaaS with Fexingo · on Risk management
  • How Jamie Dimon Built a Fortress Balance Sheet at JPMorganThe CEO Diary with Fexingo · on Risk management

More from Building Billions with Brandon Dawson

All episodes →
  • S2 EP 28 The Brutal Truth About Why 97% of Business Owners Never Reach $100 Million48 / 100
  • S2 EP 26 The $5 Trillion Opportunity Hiding in “Boring” Businesses75 / 100
  • S2 EP 25 Inside the Arizona Attorney General Race: Law, Power, and Statewide Impact59 / 100
  • S2 EP 24 Car Session: Pressure, Doubt, and the People Who Shape Your Outcome53 / 100
  • S2 EP 23 The Business Builder Blueprint: Systems, Scale, and the $5 Trillion Opportunity with Ken Goodrich58 / 100
Explore the best B2B Startups & Founders podcasts →
All Building Billions with Brandon Dawson episodes →