E1: Why we're starting this podcast

Crown circle

In This Episode:

In this episode, we talk about why we are starting this podcast. From the outside, the founder's journey seems like it’s veiled in secrecy. As current founders of a high-growth software company, we’re here to shed some light on that. 

We begin our series with talking about our own founding story and what we had to consider before embarking on the journey. 

In this episode, you will find the answers to the following questions: 

- What are the things to think through before starting a company?

- How do you decide who to partner with when starting a company?

- How do you know if you have the right business idea?

Key Takeaways
Founders' Backgrounds Matter: The founders, Alex Levin and Rebecca Greene, emphasize the importance of their backgrounds in shaping their entrepreneurial journey. Their experiences in investment banking, sales, trading, and tech roles played a crucial role in their evolution as founders.
Strategic Partnership: Before identifying a specific business idea, Levin and Greene stress the significance of first deciding to become founders independently and then choosing to partner with each other. The value of a strong and complementary partnership is highlighted as a critical factor in their success.
Passion and Conviction: When evaluating founders for investment, the emphasis is on passion, conviction, and determination. The ability to run with an opportunity, face challenges head-on, and maintain a strong work ethic are key traits investors look for in founders.
Founder-Market Fit: Evaluating whether founders have a unique insight or experience that aligns with the chosen idea is crucial. The concept of "founder-market fit" involves assessing if the founders are the right individuals to pursue a specific business idea based on their backgrounds and expertise.
Execution and Follow-Through: The founders highlight the importance of execution skills. How founders interact, set up meetings, follow up, and execute on commitments can influence investors' perceptions. A focus on individuals who consistently move initiatives forward and iterate is a key criterion for success.

Meet the speakers

Alex Levin
CEO & Co-Founder, Regal.io
Rebecca Greene
CTO & Co-Founder, Regal.io


Alex Levin: [00:00:00] Hi, this is Alex Levin and Rebecca Green. We're the founders of regal. io. And we're here with the first episode of 15 minute founders. So we want to talk a little bit today about why we're starting this podcast. Maybe as a starting point, I thought Rebecca and I would give our backgrounds. So Rebecca, do you want to go first and talk a bit about your founding story as it were?

Rebecca Greene: Sure. So I started my career out of college classically in investment banking and sales and trading. I went to Bear Stearns, which no longer exists and had the opportunity in my first year of my career to actually see a company go from, you know, fortune 500 to, to non existing within the course of a year.

And that was the first time I really got interested in, in why some companies succeed and why they fail. And I didn't know I wanted to be a founder then, but it's what made me realize I was interested in this evolution and life cycle of companies. And I ended up. Going into consulting and then went to business school, which is a life hack of how you get into tech and [00:01:00] startups without being technical at first and worked at Amazon and learned how to build technology and products from the best in the business and got excited about bringing businesses online and joined a company called Andy, which was a really early stage startup at the time in New York.

to help bring the home services market online. And I ended up being the chief product officer there. And for six years, made a lot of mistakes and grew a lot on other people's dimes. And by the time I was done, decided I wanted to go do it myself. So I joined Alex, of all people, who worked with me for that time to go build Regal.


Alex Levin: Cool. It's funny. Our backgrounds are very similar. You, you know, you were an English major. Aspiring to be a comic at the time, and you know, I was a philosophy and psychology major, so nothing technical whatsoever, you know, and I actually believe strongly it's a great way to start in sort of true liberal arts where you're following your passions, and then, you know, I smartened up as I was graduating, and I think I read at the [00:02:00] time you know, Software is Eating the World article, By by Mark Andreessen and understood that there was going to be no company that wasn't a technology company.

And I had to go and figure out what this technology thing was. And so I started working for tech startups and got lucky and, you know eventually sort of moved into product management roles where You know, I wasn't an engineer, certainly, but you know, I learned enough to be dangerous and I started trying to make my own websites on the side and learn a little bit of coding and SQL and things like that.

And it helped enormously to see how the sausage was made. After a couple different companies eventually met Rebecca at Handy and, you know, eventually ran a lot of the marketing and the growth teams there. And I think really. Over the time, got to see, you know, different founders, different styles and saw some things that I like, some things that I wouldn't do.

And, you know, part of, I think, what excited both of us as we went to be founders was that we would get to sort of do things in the way that we thought would be best for the type of [00:03:00] company we were creating. And, you know, that was taking the best from lots of different places before. You know, we've been very lucky, I think you know, going out on our own.

It's a dangerous, dangerous thing for sure. And you know, I don't recommend it to anybody, but you know, if you have that passion and you really have to do it, well, then, you know, I think our goal with this podcast is to help bring a bit more transparency into what's happening both at Regal and at other startups and talk a little bit more about what is the journey of a founder so that it's a little bit less veiled in secrecy.

I think, you know, the, the. Rebecca knows this. The thing that I love to read when I have time is these company histories. And the reason is is that you see what's really happening at the company. So, the, one of the first company histories I ever read was about PayPal. And I remember thinking of the metaphor of the swan.

We're above the water, everything was beautiful. And as an outsider, I always thought PayPal was this amazing, huge company that did things perfectly and was so great. And then you read this book [00:04:00] and you find out that under the water, that swan is just, you know, paddling furiously just to try to stay alive.

And there were multiple times when PayPal could have died, and multiple times where they sort of completely made huge mistakes, but, you know, they, they, they managed to stick with it. So, I think reading those stories is enormously helpful to me because it helps me understand that, you know, we're not the only ones that go through the rollercoaster.

And I guess that's my motivation for really starting this. So, I don't know, what about you, Rebecca?

Rebecca Greene: Yeah, it's interesting. You you know, you only read those books or see articles after the fact, after companies were spectacular successes or, or spectacular failures and there's a takedown or something like that, but I think one of the most helpful things for me as we've been building this company is being an angel investor on the side and we do that together.

And it's, you know, hopefully one day that also Proofs, you know, economically sound to do that, but I've actually valued it from a from a learning perspective. Getting to see all these founders in the moments making decisions, struggling with things, needing help with [00:05:00] things and asking for help is hugely valuable.

And I think a podcast like this can be that as well. What's happening in the moment as people are making decisions as we're watching other struggle to make decisions. You know, it removes the veneer of just the big successes were just the big failures.

Alex Levin: Yeah. Yeah. So, so let's start a bit with like the very beginning of the founders journey.

You know, we get this question from friends all the time. Like, Hey, you guys started this company. Like, how did you make the decision? Like, how did you know it was time to go do it? So when people come to you, what do you say? Like, what advice do you give them?

Rebecca Greene: Well, I mean, I tell them

the truth of how it happened for us.

I tell them about the six years we each spent at Handy building that company and learning a lot and getting to know each other and that it was an evolution that you and I first independently decided we want to build something and be entrepreneurs. Then we decided we wanted to build together with each other and partner up, which I think is the most important decision we actually made.

And then it took time, it took two years for us to find what is the business that we wanted to do [00:06:00] together. And that's the order, it's not the order that works for everybody, but I think that was a really critical order for us to come to the decisions independently that we wanted to be founders, but then to partner up first before we even had the business idea.

And then sometimes I tell them about how all the bad business ideas, or actually other good business ideas we could have built, and how there's no perfect idea. It's about kind of figuring out what's right for you.

Alex Levin: Yeah, yeah, I agree on the order. I think when, when I talk to people, the mistake they most often make is they don't have a person that they're going to do this with as complementary to their skill set.

They... They know they want to be a founder. They're kind of thinking they'll just grab anybody along the way. Or they have somebody they met like last week at a, you know, happy hour. And that's, that's I think not impossible, but makes it much harder to be successful. I think part of why you and I work so well together is, you know, you don't need to look over my shoulder.

I don't need to look over your shoulder. I know sort of your strengths and weaknesses. You know my strengths and [00:07:00] weaknesses. It makes it much easier than going into something blind with somebody. So if that's maybe the biggest mistake. The one that people focus on the most, I'd say, when talking with me is not that, though.

They focus on, what's the idea? How do I know it's the idea? Like, you know, is this the right idea? And I, you know, I've taken to sort of saying, look, you know, the sort of, that's not the right thing to focus on. Let's say you, now you found the right person you want to focus on. And I've come to saying, you know, convince yourself first.

So I think everyone's idea at the beginning is like, oh, can I raise seed money for this? Can I raise seed money for this? And it's the wrong question. You know, you should be spending whether it takes a week or a year time making sure you're convinced that this is going to be something that you're interested in for 10 years that is going to be successful over 10 years before you go and raise money.

The second you raise money, the clock has started, and now you're in a dangerous situation where. You know, you have to stick with it and you're at least in it for a couple of years while you have that seed funding and likely [00:08:00] in it for 5 to 10 years because there's going to be some success. So make sure that you know, you are convincing yourself first.

And then the way I sort of like ask people if they're convinced is are you ready every day of your life for the next 10 years? Certainly, probably for the rest of your life to explain to people this idea, because guess what? You're literally going to tell the exact same story every day of your life for the rest of your life.

And if that doesn't excite you, if you're not passionate enough that you want to tell people why this is important and why they should be thinking about it, don't do it. Even if it's a good business, don't do it. Because you're just going to get bored of it, you're not going to be able to push through when there are hard times, and there will be hard times.

So, it's a weird way of looking at it, you know, but at the beginning we don't ask them normally, How big's the market? How big is the opportunity? Who's the competition? You know, we trust that people are smart, and if they've convinced themselves... That goes a long way, but if they're not even there yet, it's not time to start.

I mean, when you know, you mentioned angel investing now. So when we [00:09:00] start looking at deals, like now having been through this a few times, like, and you're talking to founders and evaluating founders, forget the business for a second. How are you evaluating them? Like, how do you look at, is this the right team to go after something?

Rebecca Greene: That's a good question. I mean, I think of it. The best case scenario is that someone we've known and worked with before, because I think the thing you're trying to get at or I'm trying to get at when evaluating someone is something similar to what you described, which is how passionate are they about this thing?

How much conviction do they have? And will they just like run like hell after this opportunity and ignore all the naysayers, ignore all the hard times like plow through it. And that work ethic and that determination, how somebody is when they have something they believe in. Yeah. It's really hard to evaluate if you haven't worked with them before or you have to do much more homework.

You have to do a ton of references, have to look at their background, have to really dig into the ideas and the challenges that they went through. So that's number one for [00:10:00] me, is like, is it somebody who we already know who we know works like that, or can we validate that that's their work ethic? I Also try to look at, like, why this idea and why them, that combination.

Like, do they have a unique insight or a unique experience? Or did they just scour crunch base for a bunch of good ideas and say, Hey, I think I could do that better. I think that's important too. And it's still trying to get at that, that founder market fit idea of like, is this the right person to go after this idea?

And so even if they've built conviction, do we have conviction that they're the right person? Those are the two things that I, I typically look for in the, in the founder. And I guess the third thing I would say is like, did they find what you and I found? Like, did, are they looking or have they already found the partner to surround themselves with who.

Has enough overlap that they will work well together but doesn't have too much overlap that they compliment one another and they won't have to hire a ton of people to build, you know, the foundation for this business to start.

Alex Levin: Yeah, and it doesn't have to be a technical person among the founders. I think that's part of what's changed in the last [00:11:00] about five years is, you know, we're not looking to see is one of the founders technical.

Certainly they have to hire a technical person if they're not technical, certainly have to evaluate. Whether that person is gonna help them build the product, they have to know how to run teams of engineers and product people. So I think like we look for at least one of 'em to have worked as a product manager or worked as a, you know, a sort of a, somebody on the data engineering side, even if not on the sort of product engineering side.

So they have somebody how technology's built, but they don't have to be an engineer.

Rebecca Greene: Yeah. And it depends on what the insight is that they're chasing. If it's not a technological breakthrough or innovation, certainly. Like it could be a go to market innovation. It could be a business model innovation. It could be all kinds of, you know, new applications.

Alex Levin: So certainly if it's a research based innovation, for sure it's different than you expect the founders, maybe even both of them to be technical founders who understand it deeply and are going to spend their time digging into it. But [00:12:00] yeah, if I think about like that founder product fit to your point, they, I think the, the ones you mentioned are real.

The, the only other one I'd add, As a sort of an outsider evaluating is how the person sort of interacts with me does color my judgment of them. So, you know, are they setting up a meeting and showing up on time? Do they then send a follow up after the meeting with clear notes? If they say they're going to do something, do they do it?

If they ask me to do something, I'm going to go and follow up. So I'm going to go and do it that night. You know, I, I like the same thing. So if they ask me for an intro, I'm going to go and do the intro. Do they follow up and actually talk to that person? I'm going to let them go check with that person and see how that meeting went.

So especially when we don't know people, that's a one way for us to tell, you know, how on top of sort of executing is that person. And I'd say with you and I, we probably index more towards looking for people who are just fantastic at executing than anything else. Because I think [00:13:00] we've learned that those people, if they keep moving it forward, keep moving it forward and iterating.

They're going to find the answer.

Rebecca Greene: Yeah. I heard an idea today. I was listening to a podcast and it was Andrew Marx, who I met at a dinner the other night talking about this, like hypothetical of if a person you knew in your life, who's, you know, straight a student remarkable, but not like remarkable in any particular way.

Had the idea for Google, right? Like had the, whatever the algorithm could they, would that be as big of a business as it is today? And the answer is like, there's no chance, right? Like it has to be about the particular person in that particular thing. But so it's not about the idea, right? It's not just about having the idea.

It's about is that person the right person to go execute like hell against that idea and continue to see the bigger picture and the bigger opportunity. As the business unfolds.

Alex Levin: Yep. So that's a good place to end, you know, so 15 minute founders going to be digging into founders, their [00:14:00] stories the rollercoaster, their ups and downs.

And really trying to bring more transparency to this journey so that people can see that they can do it and they should do it if they believe strongly enough in that business. So looking forward to seeing you next time. Thank you, Rebecca. Thanks, Alex. Bye.

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