Molly Montgomery – Founder’s Haven | 384

founder's haven

Today on Thought Leader Thursday, Matt speaks to Molly Montgomery, a startup growth strategist and the creator of Founder’s Haven, the first resource of its kind to help high-performing founders stay connected to their greatest potential. Learn about what initially drew Molly to startups, her big realization after nearly 16 years of advising, and the worst tax strategies she’s witnessed.

founder's haven

What You Will Learn About Molly Montgomery – Founder’s Haven:

  • The importance of “personal drive” behind a business
  • What Molly did before starting Founder’s Haven
  • The biggest mistakes Molly sees founders make when starting a company
  • What initially drew Molly to startups
  • What Molly has realized after nearly 16 years of advising
  • How Molly defines a “startup”
  • The worst tax strategies Molly sees people using

Recommended Resources:

Work with me One-on-One

If you’d like to work directly with me on your business… go to, share a little about your business and what you’d like to work on, and I’ll get you all the details!

  • Would you like to meet in person? Our next live event is right around the corner! Go to for the details.
  • Become an Epic community member at The Epic Real Estate Investing Show 
    One of my favorite things to do is share with investors the latest and greatest tactics and strategic friends I make. I do it every week and you can listen in by subscribing to The Epic Real Estate Investing Show podcast on iTunes – Click Here.
  • Grab my book, Epic Freedom ($1) 
    I frequently hear from people looking into investing in real estate for the first time, “How long is it going to take?” So much so, I wrote a short book about the 2 easiest and fastest strategies to a paycheck in real estate. You can grab a copy for $1 and I’ll pay the shipping – Click Here.
  • Join our Badass Investor Program and be a Case Study 
    I’m putting together a new Badass Investor case study group at Epic Real Estate this month… stay tuned for details. If you’d like to work with me on your real estate investing, go to to get started.
  • Also, check these out:


Thank you so much for joining us on this episode of the Epic Real Estate Investing podcast!  Please subscribe to the podcast so that you will get instant access to our new episodes.

If you found this podcast helpful, please take a few minutes to leave us a positive review in iTunes.  Your reviews help to improve our search rankings so that we can spread the love.  Thank you!


Matt Theriault: Hello. I’m Matt Theriault of the Epic Real Estate Investing Show and this is Thought Leader Thursday. Today I’m joined by a startup growth strategist and mentor to high performing founders and visionary leaders. She helps founders grow or scale their company with confidence and peace of mind. She is the creator of Founders Haven, the first resource of its kind that helps high performing founders stay connected to their greatest potential while helping elevate the immense pressure that comes along with being the creator of a high growth company.

So, it seems like something that’s well needed in today’s society. So, please help me welcome Molly Montgomery to Epic Real Estate Investing. Molly, welcome to the show.

Molly Montgomery: Thank you so much for having me, Matt. I’m happy to be here.

Matt: Good. Glad to have you too. Before we get into your work as a startup growth strategist, what were you doing just prior to getting involved with that?

Molly: So, I started my career about 12 years before I went off into the entrepreneurial myself. I spent 12 years in public accounting. And my background, my technical training, my career capital is all built up in public accounting.

I’m a CPA and spent several years working for the big firms. I did a nice long bout of audit work. And then went and got my master’s in taxation. Then got involved in doing a lot of forensic investigations and litigation support.

So, I eventually got to a place where the entrepreneurial bug was constantly nagging at me through that entire 12-year journey. I saw in the companies that I was working with, all this transactional work that I was doing, I was always the one that was sitting at the table after the fact, after all these things had already happened. And then something was going on that people were trying to accomplish. Whether it was a sale, or in the case where there was fraud or something went terribly wrong. I was the one sitting at the table looking at all the past saying, “Okay, well, now here’s where you are. It’s not quite where you were hoping to be right now. So, if you would have done A, B and C years ago, you would be in a different place.”

That was the perspective I constantly was seeing. And so there was just this gap. This gap for companies a lot earlier on their life cycle that I started to have this real passion for wanting to help companies earlier on. And I really started to see the need and the desire for it.

So that’s when I ended up leaving the corporate path that I was on and started up my own consulting practice and doing just that. Working with companies that are younger. Getting things going, getting that foundation set early on in the game.

And one of the things I realized at this point … 15, almost 16 years of advising … I really got connected to the personal side of what people were going through, and why people are making certain decisions, and just helping support the personal journey they’re going through while growing their business. Especially as it relates to a lot of the real estate investing and pooling your wealth, and expanding. Why are we all doing what we’re doing?

There’s the business aspect of why the business exists. But then there’s the whole personal side of what’s going on behind the scenes with what is your personal drive of why you’re even doing this.

Matt: So you have all of this, I don’t know, kind of this hindsight of where you’re able to clearly see where they could have made some different decisions and ended up in a different place where they wanted to end up. So, you went out and you went to take that on. Give me a story or an example of when you realized that, “Wow, I’m really good at this. I can really make a big difference here.”

Molly: It started while I was doing the advisory work. When I was working in the public accounting world, I worked for four or five different accounting firms. It wasn’t something where I went and I started working for … I worked for Ernst & Young for a couple of years.

And then I went off and I actually did the first round at an attempt at entrepreneurship. Left the audit world. I went and started to get involved with real estate investing. Trying to navigate through a lot of different things. I became a personal trainer. I started my own accounting practice. And I was just doing all this small business advisory stuff.

And at some point, that’s when I really started to make the connection between to see the personal passion and the personal drive behind the business owners that I was working with was in that small business setting.

And when I got into the forensic work … so once I went back to school, got my master’s degree, and got into some of these really big forensic investigations … getting into the conversations with people, seeing the psychology behind what was happening, and all of the challenges. The emotion, the relationships, navigating through all of that while doing the actual forensic work, I really connected to that part of what was going on in those situations.

Matt: Every time I hear the word startup I always think of Silicon Valley for some reason. How do you define a startup? Is it just someone that’s starting a company? Is that how you define it? Or do you have a more narrow definition of that?

Molly: The way I define it, the way I look at it is what is the intention behind the business that’s being started? What is the growth trajectory that the founders are aiming for? What is the ultimate end goal of what they want to be doing with this business? And are they seeking investment?

Just different factors that come into play that really start to define as it separates out is the money that this company’s generating, is it intended to be more of a family-owned business or a lifestyle business? Are the earnings intended to be withdrawn from the company? Or is this truly a company that is intended to be built? A whole separate entity grew into something that is separate from the people who start it?

Matt: What are the biggest mistakes that you see founders make when starting a company?

Molly: There are a couple. When starting it … or when growing it … there’s what I just described at the distinction between what is the intention with the business, and the cash, and the profits that are going to be generated with the company.

If there’s investors involved that creates a certain type of environment versus if someone is starting a company and growing it organically. Or getting it off the ground organically.

It’s quite common that I’ll go in and see a company that is having cash flow problems, which most businesses that are just a couple of years old are having cash flow problems. That’s just part of what you deal with.

Looking at the financial statements compared to what they are saying they want to be doing and what the founders are saying they are creating. Because you can tell by what people are saying versus what the actions are of what they’re doing with their finances. If those are out of alignment, then the whole company is going to be a mess. So, that’s one thing.

And then another thing, just really understanding that to grow a business you have to have the systems in place to grow the business. You can’t grow a business on the shoulders of people running the business, running those systems.

Matt: Absolutely. As an educator, a consultant, a strategist, an advisor myself there’s all types of crazy advice out there that kind of gets on my nerves when I hear it. And I hear it over and over again. It just irks me. I was like, “No, don’t say that. Or don’t follow that.” What one piece of bad advice in your world that you see or hear frequently that really bothers you?

Molly: Since I have a background in the accounting tax finance world, it’s always interesting to me how people talk about the different types of tax strategies that their advisors are doing for their company. And they go off and they call somebody up and say, “This is what my guy’s doing for me. Why aren’t you doing it?” Then people start taking action on advice that they’re getting from their friend without talking to their advisors.

I see so many messes where people try to do their own tax planning, which there are certain foundational things that, yeah, as you learn about them they become more standard and “basic” when it comes to tax planning. So you can start doing that for yourself. But, my gosh, don’t take tax advice from someone who’s not a tax advisor.

As you said, there’s so much bad advice.

Matt: That’s all right. No, just the fact that you have multiple answers I think is fantastic. And what would be the best way for them to reach out to you?

Molly: So, you can come, find me online. LinkedIn. I’m pretty active over there. I love connecting with people on LinkedIn. So that’s Molly Montgomery . You can also come, find me on Facebook or Twitter. So Facebook, Molly Montgomery there as well. And then Twitter, it’s @mollym_cpa.

And Yeah, I’m going to be putting out a lot of content out there as far as those moments when you’re in those make or break decisions of just comes down to needing to navigate through what path to take. Some really common conversations that I get into. I’m going to be helping people navigate through that.

Matt: Super. Well, I’ll make sure all of that is really easy to find inside of the show notes and everywhere else that we’re present online. So, I’ll make that easy for them.

And it’s been an absolute pleasure. Let’s do it again sometime.

Molly: Fantastic. Thank you so much, Matt. Absolutely.

Matt: You bet. Okay.

All right. That’s another episode of Epic Real Estate Investing. Specifically Thought Leader Thursday. We’ll see you next Thursday again. Take care.