Episode 06

How I Use Data To Help Democratize the Access To Capital

In today’s episode featuring amazing entrepreneurs, Steve welcomes Keren Moynihan, founder and CEO of Boss Insights. She shares her path for empowering banks, credit unions, and lenders through the organization’s digitized system. This includes how they’re partnering with various lenders by providing them the services they need. The team has a webinar coming out, aiming to improve your growth with API data.

Boss insights speed up the lending process from months to minutes, especially for small businesses. It provides lenders the ability to visualize financial attributes while giving them the credit that they deserve. There is so much going on with all the alternative lenders and technology from a data perspective. And according to Keren, people tend to forget that the business lending process is disrupted, particularly for humble and commonplace transactions.

How Does it Work

Boss Insights provide business data for business lenders. Keren says that as a former financial service worker, she knows how loans can consume a lot of time and energy. To bridge this gap among banks, credit unions, and lenders, Boss Insights quickens the lending process.

On the side, the credit union has its members. These CUs must show projections on what their business is saying. Although banks hire people like Keren, who would conduct the calculations along with the credit talk, the process is not convenient and might take months to accomplish. But nowadays, there is another pipeline that gathers cloud base information to bring out secured email transparency. It goes by grabbing the date when there is better capital experience.

Keren emphasized that it’s not just from the investment point of view. Considering the year of digitalization, financial brand posts and American banking association posts about modernization are everywhere. Meaning, it also comes with a technological perspective.

Matching Aspect

Bank companies’ services are getting endless, inducing Boss Insights to create a matching program. And whether for the investment side or on the lending side, they would offer price to anyone who wants to help the ecosystem. Keren mentioned that even though there are incredible platforms out there matching people, it’s not really getting into the weeds. One must catch up with algorithms.

Digitized consolidation of forms is the newest trend at this point. Gathering and automating information saves the ecosystem without compromising the value of the service. Plugin happens when the business gets the email and checklist.

People need to understand that when they have a hard challenge in front of them, you need to quickly decide, compete with tech firms out there with alternative lenders. For example, the owner has to quickly decide to work on the appropriate advertising platform like social media or email linkage. There is a product that the applicant can choose from. The loan officer, together with the credit risk manager, will evaluate and approve typical applications.

According to Keren, businesses are the economic engine of the future. Society has to be able to evaluate people fairly and without bias and not relying on old techniques. And she was hoping that the team would always serve and create a difference and democratize access to capital for whoever wants it.

Economic Engine of the Future

Keren mentioned that they set Boss Insights to be remarkably business-friendly while being on their partners’ side. It is more than the loan officer; it’s also their credit risk manager that has to look at things. So the right person is getting the correct information to see you. And if you’re a typical case, you get approved right away.

In terms of operating or improving things, Keren stated that she wasn’t going to say anything revolutionary when it’s all about the people’s welfare. It is essential to be humane while contributing to society, and it’s hard to execute it from an internal perspective. That is why she emphasized delighting banks and credit unions to further delight businesses.

You can either build your lending platform similar to Amazon or Shopify for eCommerce and lending. An individual can be a regulatory expert as a financial institution and leave it to the tech people to help them rest. That is why Boss Insights are here to assist you with the same goal you wanted to accomplish. Keren needed to instruct herself on how to evaluate who’s there to support that.

Initial Stepping Stones 

The Boss Insights is building up the team, conducting initial hires specifically for sales. Keren mentioned that the organization is hiring for an ad, looking for people who claim the position and proactively say mine. She wanted someone who can challenge her from day one while serving the Boston sites.

Diving for diversity and a multicultural environment has a concluding result, which is having a stronger product. Working with a peer platform and serving each party’s needs would quickly help you reach the project. By this, Keren mentioned how they worked with Luke, the one who scaled Amazon. He then saw things from a tech perspective since businesses do not have the expertise and time to approach it.

That is why the team brought in somebody with excellent data and strategy, explaining they hire for talent while being inside an environment with a multicultural state and amazing corporate culture points. And there is a vision here, a future that is not based on looking at businesses on their collateral, but on their merit.

The Demand for Digitized Business Data

Because of the shift to the demand for digitized business, society’s bargain requires humanity without compromising service value. One of the initial steps Boss Insights took is hiring people who own their job, not someone who says some aspect is not part of what they signed up for.

Technology is a challenging business tool for people without prior knowledge about it. With the right partnership, there can be enormous development with service and humanity at both ends.

In the end, banks, credit unions, and lenders do not just transact for present gains. Keren said that how they see and work to where they are going will surely beat the financial and business world gap.


Steve McGarry:

Hello Welcome to The Exit presented by Flippa. I’m your co-host Steve McGarry, and this is a 30 minute podcast featuring amazing entrepreneurs who have been there and done it. We talk through everything from buying businesses, selling businesses, operating businesses, and just the stories of these incredible entrepreneurs. So you get to learn how they did it, the tricks and tips of just grinding day in and day out of building these businesses.

Before we dive into my interview today with the CEO of Boss Insights, Keren Moynihan, definitely check out the links in the description as well as the show notes, to check out my interview previously with Yaro Starak. There’s some incredible content in there where he talks about coaching entrepreneurs and buying and selling his previous businesses. So definitely be sure to check that out.

Now on this interview, this hits home with me because I was previously operating a business that was in the peer-to-peer lending space, where we were financing students to go through coding boot camps. We sold that business to the founder of PayPal, Max Levchin years after we had started it. So this one hits home with me. Boss Insights accelerates the lending process from months to literally minutes for small businesses. It just really gives lenders the ability to visualize and simply give these small businesses the credit that they deserve.

So it was a lot of fun sitting down with Keren and learning how they’re doing this, how they’re partnering with lenders of all different shapes and sizes out there and getting all these small businesses the help that they need. So without further ado, let’s dive right into my interview with Keren Moynihan, the founder and CEO of Boss Insights.

What is up everyone? I am here with Keren Moynihan, the CEO of Boss Insights. How are you doing today, Keren?

Keren Moynihan:

I’m doing great. So great to be here with you.

Steve McGarry:

Yeah. We’re really excited to dive into your story and everything. And Boss Insights drew me, drew my attention right to it because having somewhat of a background in peer-to-peer lending, I was really excited to see that you guys are really helping visualize the benefits of small businesses to lenders and things like that.

So before we dive into Boss Insights, I’d love to learn a little bit more about your story and what brought you to create Boss Insights and just kind of your entrepreneurial path leading to today.

Keren Moynihan:

Sure. Great question. I think in some ways looking back, because hindsight’s always 20/20, I was always going to be some kind of entrepreneur, it’s in my blood. I think it’s now third generation in my family. But I was not raised to be an entrepreneur. I was actually raised to go into big business. And like some other people I know, as I just found out, it wasn’t for me.

I found myself in the last financial crisis that we had working at division of a Stock Exchange. And then right in the thick of the aftermath of it, I was working at a top five bank, as a commercial banker. And every time I… I guess I’ll say my job was to bring in new businesses and grow the businesses and build relationships. That was supposed to be my job. My job was actually gathering paper and pushing paper and becoming a human calculator. And every time I saw something that could be done better, it was always in my nature to say, “Well, why don’t we just do it better?”

And that’s just not how big business works. There are processes and there’s reasons for that. And they’re great at regulation, and I don’t think that point should be glossed over. That’s not me though.

So I found myself in my career moving more and more towards entrepreneurship until I started my first company in 2014, which was in finance, giving big buildings money to make them more energy efficient. That had to have a financial component and it had to have a greater impact. That’s what makes me motivated.

And then when I sold my stake in that in 2017, I had to make a decision. Do I want to go back and work in financial services? At the time I was doing wealth management, not commercial banking. Or do I want to work in a startup that will really disrupt the face of business lending in general? And I didn’t look back. [inaudible 00:04:35] didn’t look back.

Steve McGarry:

Nice. What was the selling your share process like? I mean, I think a lot of people really, when they hear an exit, they think of all of this kind of glamor and they don’t really see what goes on in the background. But was it someone that was already in the business that kind of bought you out? Or was it somebody external?

Keren Moynihan:

It was somebody who wanted to be in the business. So this was not a splashy, capital E exit. There was benefits from it, and it, along with mining light coin in a basement allowed me to start my next venture. We’re all scrappy and hungry as entrepreneurs. But it was not that at all. It was more detail-oriented and legal in nature. I think that’s how I would categorize it. And that is the nature of things when there are multiple interested parties. You really have to make sure that everybody is looked after if there are conflicting interests. It gets into lots of discussions. We could do a whole talk show on that.

Steve McGarry:

Well, I appreciate the going into the lending space, because I think a lot of people that are even in finance, when they think about lending, they don’t really see the benefits of helping small businesses. Because the majority of the frothy returns in lending is made with big loans, and small businesses don’t necessarily always need a lot of money. And that’s not always as attractive to lenders. So when I saw what you were doing, I thought it was really interesting to kind of visualize and help small businesses work with lenders in a really great way. So what is Boss Insights now, if you could give us kind of a high level of it?

Keren Moynihan:

Okay, first off, that means so much because it started really from one person scaling Amazon and saying, “Hey, we could apply this tech to lending.” As you see a lot of the big tech is doing right now. And one person sitting in an office, not loving their job as a commercial banker, but to hear that it’s pulling you in is great. Because we sometimes forget that these businesses are just people, people with families. But I will never forget that because I heard those people, hundreds of them brought to their knees by the process. And I hear the echoes. And when 2020 happened, it’s almost like I saw the wave coming because I’d been there in the past in a smaller crisis.

But Boss Insights quite simply is, it offers business data as a service. What the challenge is in banking right now is that the business lending process is broken and it’s broken for small and medium business. It’s also broken for commercial business. We tend to forget that, because there’s so much splash with all the alternative lenders and tech and small business. From a data perspective, data’s data. If you are giving information to banks, the right information for the right purpose at the right time, they can process a loan that’s $50,000 or $250,000. They can also process loans that go up to $25 million.

I was in commercial. I had a huge bandwidth from 250 to 25 million, and that’s not the SMB. But what we’re doing really is making sure that we bridge the data gaps for banks and credit unions and private lenders so that they can accelerate all parts of that lending process, which very wordy, very complex. The way banks do it now is that they go by product. So you’ve been there where you sign up for something and you have endless forms and you’re filling out your name endless times. But why? If you grab the data once and you can apply it wherever it needs to go, wouldn’t that make for a way better experience and also some capital? That’s what we’re going for at Boss Insights.

Steve McGarry:

Got it, got it. So in a way, let’s say I’m a credit union and I want to help more small businesses, and I need to be able to get the data on these small businesses. You guys would partner with the credit union directly and then help them visualize the benefits of lending to like a local small business. Is that right?

Keren Moynihan:

Yeah. For credit unions, who I love it, they call their business clients members, because of how they’re set up to serve their members, not necessarily the shareholders. It’s just a different approach to financial services.

And the first thing that happens is you take a look at a business, and in 2020, that look is digital, but you take a look and you say, “Can I have your financials? I want to see where you’ve been. And I’d like to see where you’re going. So send me projections.”

Financials are numbers that are created by accountants and they’re on these PDF forms. And it’s really challenging to get that information. So the bank hires people like me, the role that I was in, so that we can calculate one number divided by another number over and over and over again, and then argue with credit to talk about that one number divided by another number over and over and over again. And that’s what makes it take months.

The projections are just numbers on an Excel file. They could be anything. But we’re taking them because the job of the relationship manager is to see, do I believe what this business is saying?

Well, there’s another way. And it’s with APIs, which is a fancy way of saying a pipeline that gathers the cloud-based financial information that businesses are collecting on QuickBooks or Zero or FreshBooks or any number of accounting software providers, and suck it in that way. Now, it helps the business because now it’s just a cure. It’s not an email. It also helps the business because it’s transparent. So the lender gets it, they can score it immediately. And it takes one day to change from how banks are doing it now to doing it in this way. That’s something that we usually have to chat about a bit with banks. And they go, “Really, one day?” Like, yeah, that is just a one day change for you to have access to this information in real time versus waiting for a business to send it to you. That’s a one day shift.

Steve McGarry:

Got it. Wow. One day shift. So one of the things on the Boss Insights website that I was intrigued by because my previous company was in peer-to-peer lending and we were raising money from investors and investing in students to go through accelerated learning programs. It was really low-risk profile because they were getting jobs on the other side. So the investors were getting access to quite a lot of unique investments. And I saw that you guys had like a matching component to this, like an investor matching. And that, I’m always drawn to the peer-to-peer aspect of things. I think that that’s very disruptive. So what is the matching part of Boss Insights?

Keren Moynihan:

So the matching part was something that some investors originally asked us for when we were engrossed in that market, because it’s a really exciting market, the investment space. Are you going to bet one out of 10? Are you going to bet two out of ten? What are you going for, right? And I want to hear so much more about your story actually, now that I hear you are helping the students get their legs and get on their way because sometimes you finished school and there’s this moment of, I’ve been in a program of some sort for my entire life I’m supposed to now know what I’m doing? No one prepared me for any kind of adaptive thinking. So that’s amazing what you were doing.

But the matching is that… I feel like it’s a little bit of Tinder out there. I don’t know if you’re feeling that way, but… And it’s not just from the investment point of view. It’s also, when I go to a bank, they’re experiencing some very fatigued version of FinTech Tinder with murky mandates. They like to digitize. 2020 is the year of digitization. We see it everywhere, in all the financial brand posts about it and American Banking Association posts about it. It’s the year of digitization.

Well, digitization is this huge, vast word. And it can mean anything from gathering an electronic document to automating the complete forgiveness application on PPP, on a form that had Twitter memes of monkeys throwing computers against walls. So what are we talking about? Meanwhile, banks are getting endless, endless hits from tech vendors saying, “Hey, I can solve all your problems.” And it’s a lot. So how do you match those?

And that’s what we created the matching program to do. Whether it was on the investment side or on the lending side, from a tech perspective, you’re taking column A and matching it to column B. And we offered it, and if anyone’s listening, we’re still offering it at a crazy, ridiculous price to anyone who wants to help the ecosystem, so we can all move forward. Because the point is that if we’re all rising, we’re all rising together.

So we noticed that at conferences you would meet with so many people, but nothing would really happen. And even though there’s these incredible platforms that are out there matching people, it’s not really getting into the weeds. So you have this algorithm anyway. So we just sort of take it. Let’s make the ecosystem better.

Steve McGarry:

Let’s say I’m a coffee shop in Miami. And I want to go and get a loan from a local credit union, or even a bank, some lender of sorts in my area. What does the bank sit in front of when they’re making that decision through Boss Insights? Are they sitting in front of all my financials they’re pulling in from QuickBooks, they’re pulling in from all these different types of aspects that they wouldn’t traditionally be able to see? And how are they getting that information from my coffee shop? Do I like plug in my square? Or how do I get that?

Keren Moynihan:

Exactly. So that’s exactly what you do. So you have your coffee shop and you’re saying, “Hmm, I’m sitting on a lot of people not paying me quickly enough. So I need a working capital loan. That’s what I need. I have the sales, they’re coming in. I can show that. But I need to get something to get me over the 60 days that it takes for people to pay me.”

So a bank would traditionally send you an email with a checklist. “Please send me A, B, C.” Having been on both sides of the equation, it really kind of goes down to Zed. Please send me all… I should say Z, shouldn’t I? I just outed my country of origin, didn’t I? “So please send me all of these details.”

And then if that’s not good enough, and let’s be honest, in 2020, in this interest rate environment, banks are not making a lot on these loans, but they’re taking all the risk. So they need to understand… They have a hard challenge in front of them. They need to quickly decide, compete with tech firms out there, alternative lenders, and they need to be able to make you experience a delight moment, because when you’re not working in your coffee shop, you’re on social media and you have delight moments all day long. Right? You have targeted advertising. And so you’re getting a very customized level of service. And then you go to your bank.

How it looks now is you have this list and you have to go to the bank and A, know exactly what product you want as if you were going to the grocery store. But you’re not a financial expert. And even me who worked at a bank, I don’t know all the bank products. So how could you expect to be. And then B, you’re supposed to give all your information.

Here’s the real problem. They have to then calculate that manually. And then they have to do it again when they look at you to make sure you’re still a business in good standing. So let’s switch and say what are we doing? We’re sending you an email and it looks like it’s coming from the bank, a community bank, a regional bank, national bank. It looks like it’s coming from them. And they say, “Great. If you fill in a couple of pieces of information, we’ll tell you what offers are open to you.”

And so you get that moment of, wow, I have these things that I could get access to. And then they say, “Okay, but to verify you and approve you, I actually need information. So click here to connect your QuickBooks. Here’s all we’re going to pull.”

You’re in the driver’s seat. You decide whether you want to share it with them or not. We really set it up to be very business-friendly. And then you see immediately how they see you. So you can see if they think you’re a good bet or a bad bet right away. You’re not waiting. And also on their side, they’re not waiting because it’s not just that loan officer. It’s also their credit risk manager that has to look at things. So the right person is getting the right information to see you. And if you’re a typical case, you get approved right away. So that’s the one day change.

Steve McGarry:

Cool, cool.

Keren Moynihan:

That was really wordy. Sorry.

Steve McGarry:

That’s all right. I can totally see it happening and giving it all kind of a hub where people can sit there and make a more informed decision. I think that that’s fantastic.

So shifting gears a little bit. In terms of what I always like to ask people from their entrepreneurial journey, like before your exit, what would you tell yourself 10 years ago? Knowing everything you know now, what would you tell yourself, like a 10-year-ago Keren that’s on the hustle and really trying to work hard? What would you tell yourself that you wanted to either do differently or things that you could do operationally that you would improve on?

Keren Moynihan:

Oh, this is a crazy week to be asking me that because of what’s going down in the business. I don’t think I’m going to say anything revolutionary when I say it’s all about the people. I think we’re having a little bit of a moment in humanity. Is it important to be good? Is it important to bring your best every day? Is it important to show up and make sure that what you do contributes?

I don’t know that everybody feels that that is part of the bargain as being part of society. We talked about the three things that businesses need, and it’s hard from an internal perspective at Boss Insights, it’s hard from an industry perspective. We need to show up every day and delight the banks and credit unions so that they’re going to delight the businesses.

And the reason I do it is because businesses are the economic engine of the future. We have to be able to evaluate them fairly and without bias and not relying on old techniques that we know don’t work, but we do it anyway because that’s what we’ve always been doing.

The thing that I would tell myself or the thing that I wish I could matrix into my brain is a way to quickly evaluate who is there with the right intentions and who can deliver because it is not easy. It took someone who scaled three companies, and one of them was Amazon, on the tech side, to be able to do it in this way. It’s taking someone on our team who ran data and strategy from TransUnion to do this. And I’m hoping that what I’m bringing to the table with the… I’ve experienced the problem that made me want to just, when I was in my day job. We really are there to create a difference and democratize the access to capital for whoever wants it.

You can either go and build your lending platform and be like an Amazon, or there’s Shopify for e-commerce and now for lending. And we’re like the Shopify. You don’t have to do this. You can be a regulatory expert as a financial institution and leave it to the tech people to help you with the rest. And we won’t eat your lunch and we’re not looking to be an alternative lender. We literally are here to serve the same goal that you are looking to serve. That’s what we’re here for. I wish I could instruct myself on how to evaluate who’s there to help with that.

Steve McGarry:

Excellent. Well-said. And the final question, because now that we’ve gone over your background, we’ve gone over Boss Insights, we’ve gone over kind of what you would change about how you would view things in the future, how you would change things. So that is up to team. What was the initial stepping stones for building out your team? I think a lot of listeners are always curious because hiring, as everybody knows, is very difficult, especially in the early days, because you can make a misstep with one or two hires. And if you’re only like a three person team, it can be very, very difficult. So what does that look like for you? As you were scaling up or building out Boss Insights, what were the initial hires?

Keren Moynihan:

And we’re hiring even right now, so we’re going through this because we’re hiring in sales. And the great thing about salespeople is that they sell. And the hard thing about hiring them is that they sell.

We are looking for people who… You know when you’re playing volleyball and people say, “Mine.” They proactively say, “Mine, I got this.” We’re looking for people who do that. They don’t say, “Well, that’s not my job.” We never hire for fit. We hire for add. I want someone who can challenge me from day one. But not just a challenge, but to say this is what you’re not doing as well as you could be doing to serve Boss Insights. And here’s how I can help you do it better. And then allow me to do the same thing.

The first person at Boss Insights wasn’t me. It was the CTO. His name is Luke, and he’s the one who scaled Amazon. And he worked at a company called Points. Amazing corporate culture at Points, shout out to Points. And he worked at Dealfind, which was a company that scaled very quickly as well. Right?

He saw it from a tech perspective and he said, “Businesses do not have the expertise or the time to do this.” And I said, “They don’t have the inclination either, unless they’re trying to get money.” When you were working on your peer-to-peer platform, they needed you, so they’d give you whatever you wanted, right? It’s for your help.

So I was the second hire. We then brought in somebody at data and strategy. But we hire for talent and we’re lucky enough to be in a place that’s pretty multicultural, and we get a lot of diversity. And all the stats show that if you have diversity, you have a stronger product.

We’re always looking for more of that. It’s not there on a checklist. What’s there on a checklist is a little bit of what you get when you hear about Tesla. You know? Come here, do your job, raise your hand, don’t sit on anything, ask for help, don’t be stupid. I’m actually quoting their employee handbook. Don’t be stupid, and we won’t have to react to anything stupid that you do. I’m paraphrasing, but that’s what we’re looking for.

And there is a vision here. A future that is not based on looking at businesses on their collateral, but on their merit. Where are they going? Not where have they been? Where are they going? How can we look at the information and judge them on where they’re going to go? And anyone who’s into that, we would love to work with.

Steve McGarry:

Excellent. Excellent. Well, that’s all the questions I have for you rolling out the red carpet. Where can people learn more about Boss Insights?

Keren Moynihan:

Okay. So that just flew by. And we’re on LinkedIn at Boss Insights. Our website is Bossinsights.com. You can see a theme going on here. We actually have a webinar coming out and it’s called Relate Better, Mitigate Risk, and Improve Results with API data. It’s coming out with the Bloor Group on the 22nd of September. I’m pretty responsive. Reach out.

Steve McGarry:

Perfect. Well, thanks so much for coming on the show, Keren, and all the links will be in the show notes if you guys are listening on Spotify or iTunes. But once again, thanks Keren.

Keren Moynihan:

Thanks for what you’re doing. This is great.

Steve McGarry:

Thanks so much for sticking around. It’s the end of this episode of The Exit podcast presented by Flippa. As I said before, all of the links will be in the show notes. So you guys can get a chance to check more out about Boss Insights and learn how they’re really innovating on the lending process and moving it from months to minutes.

So this was a really great episode, but we would love to have you subscribed. We’d love to have you commenting who you’d like to see on the show next. So definitely leave us a comment. Be subscribed because we have some amazing interviews lined up in the coming days and weeks here at The Exit Podcasts. So leave us a like, and I will see you guys on the next episode here on The Exit.


Steve McGarry

An entrepreneur, content creator, and investor based in sunny Tampa, Florida. In 2015, while living in San Francisco, Steve sold his first fintech startup LendLayer to Max Levchin’s (founder of PayPal) consumer finance company Affirm.

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