Modernizing The Capital Raising Process With DealMaker’s Mat Goldstein

Raising capital can be a tedious process, even after investors have agreed to commit capital. 

This realization was the catalyst for experienced Bay Street lawyers Mat Goldstein and Rebecca Kacaba launching DealMaker—a digital transaction management platform that provides a seamless, headache-free investor experience. Since the platform’s inception in 2018, companies of all sizes have used DealMaker to launch and market their offerings to investors across the globe.

In this episode of The Modern CFO, Mat talks with host Andrew Seski about the future of digital capital formation and what sets DealMaker apart from other cloud-based platforms offering capital raising solutions.

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‍Show Links

• Check out DealMaker
• Connect with Mat Goldstein on LinkedIn
• Check out Nth Round
• Connect with Andrew Seski on LinkedIn

Transcript

Please note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.‍

[00:00:00] Andrew Seski: Hello everyone and welcome back to The Modern CFO Podcast. As always, I'm your host, Andrew Seski. Today, we're joined by Mat Goldstein, co-founder of DealMaker. Mat, thanks so much for being here. 

[00:00:20] Mat Goldstein: I'm delighted to be here. Thanks, Andrew. 

[00:00:22] Andrew Seski: So before we kick off, let's talk about DealMaker and what it is. What does it mean to turn a simple capital raise into e-commerce?

[00:00:30] Mat Goldstein: Yeah. DealMaker, first and foremost, is a technology company. Our platform is used by issuers. You know, think, when I say "issuers," think "founders." You know, companies who are raising capital, who are looking to solve an age problem of how to engage with prospective investors and turn them into a source of capital. Using our software, an entrepreneur can start an online store and run a full e-commerce campaign, identify leads, create a relationship with a community, engage with that community to turn it into a source of capital, and rely on the analytics, payment processing, and full set of functionalities you'd expect in a Shopify store. You can leverage that for a capital raise campaign. So that's what we mean by turning raising capital into e-commerce. It means using the internet as your medium of sale and using the tools of e-commerce to identify an audience, engage with it, and turn that into a source of capital. 

[00:01:38] Andrew Seski: So let's talk about how you identified the need for DealMaker and what actually catalyzed the entrepreneurial spirit in yourself to go start something new. You were a lawyer in your previous life. So now, are there no efficiencies when it comes to the legal frameworks of startups? Because I'm sure between all of the different types of offerings, whether you're doing Reg CF, Reg A, Reg A+, and having all of these actually change a bit probably over the last 10 to 20 years between the US and Canada, did you notice any major inefficiencies that catalyzed your, you know, desire to go try to solve some with technology?

[00:02:16] Mat Goldstein: Well, Andrew, that's what we lawyers would call a leading question. You're right. So look, you know, Rebecca and I started this company back in, you know, back when we were still practicing law early kind of 2017. We did our beta in 2017. We started planning the company earlier in 2016. We were both partners at an international law firm. And in our daily practice, we dealt with technology companies and we came to understand that kind of lean startup mentality of how to solve a problem using technology by build-measure-learn. And we, you know, one day, we sat down with a whiteboard and we mapped out what the steps were in a capital markets transaction. 

[00:02:58] And when I say "capital markets transaction," I really just mean a company selling shares, right? And it's crazy. I mean, you have to identify, there are eligibility requirements when you're selling chairs in the exempt markets. I can get into all that. It's like, you know, you've got public companies who are listed on stock exchanges. They have a whole infrastructure to raise capital, and it's automated, and it's built on, you know, brokerage houses where you go into your Robinhood account and you press "buy" or "sell." And, you know, technology takes over. The private markets have nothing like that. Just nothing. If you and your co-founders were raising capital, which, you know, you've done so you can talk about, then you're in the exempt markets. You're not a public company. You don't have access to that infrastructure. So you need a lawyer to draft a subscription agreement. The investors have to be eligible to buy exempt market securities, which means they need to be accredited in some way or the offering needs to be qualified in a different way. They'll need to fill in the certificate, they'll need to send in the money, the money they send in has to match the order on the form. And there's a whole nine depth, you know, kabuki dance to get to a closing, which just costs everybody time, money, and headaches. 

[00:04:15] And so, we looked at that and said, "Well, isn't raising capital really just sales?" Right? And that's something you and I have chatted about before. Isn't it just sales? How is it different? You're identifying somebody who, you know, likes what you have. You've got an ideal profile in mind and you wanna eliminate any friction in between them liking what you have and, you know, you making the transaction. And so, there's a playbook for this. It's called the internet. And if you think back to the early days of e-commerce, you had shoe stores who would go to like Accenture and custom-build a website to sell shoes online. And along came Shopify and said, "You don't have to do that anymore. We built a platform. You can license an online store and it has everything you need to run a campaign on the internet and you have to find the buyers." That's the Shopify model. And that's our model as well. 

[00:05:20] And at the end of the day, there's just some stuff you can't outsource or automate. If you are a founder, it's you that people are investing in. You have to be front and center of your store. But we built a technology platform that puts the issuer front and center, puts the founder front and center, and going out to raise capital then becomes an exercise in, you know, e-commerce, right? Identifying the prospects, engaging with them in a way that, you know, speaks with them, that they connect with, using analytics to see who's likely to close, right? All of the tools of the modern kind of sales funnel management — the CRM, the prospecting, the elimination of friction in getting an order form signed, elimination of friction in taking payments online using credit card — we built all of that. 

[00:06:10] And over time, it became, you know, something that, I think it's true whenever you introduce innovation into a market, there's a dynamic, right? The market response, the innovation, and it unlocked people's minds. So in the very early days, right, there were, you know, people who were raising capital from friends and family and from kind of pre-IPO rounds and following the same steps that traditional capital raising would follow. But over time, as people came to really und...