In this Founder Wisdom Pod episode, host (Speaker A) interviews Jenny Kassan, an attorney, author, investor, capital‑raising coach, and co‑founder of Opportunity Main Street. Kassan explains her mission to help the roughly 83 % of U.S. businesses that lack access to traditional bank loans or venture‑capital funding by offering alternative financing structures. She describes creative term‑sheet options such as revenue‑based financing (both debt and equity), equity with buy‑back provisions, dividend‑bearing equity, and other customizable arrangements, emphasizing the near‑infinite flexibility of these deals. Kassan discusses the role of crowdfunding under the 2016 U.S. law, highlighting her regional platforms (CrowdfundBaltimore, CrowdfundMontana, CrowdfundMainStreet) that enable accredited individual investors to fund local businesses. She outlines her ideal client profile—impact‑oriented, non‑VC‑fit businesses—and the ideal investor persona—non‑professional, accredited individuals or small foundations seeking alignment with values. Kassan’s fee model combines flat‑fee legal services with a percentage of funds raised on her crowdfunding sites. The conversation turns to her current real‑estate project in Baltimore, a renovated building intended to house entrepreneurs and channel community capital, noting progress, remaining fundraising needs ($1.7 M raised, more required), and challenges such as renovation cost overruns and tenant acquisition. The episode concludes with Kassan’s goals to complete the Baltimore project, replicate the model in other communities, and invites listeners to learn more online.
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Welcome to another Founder Wisdom Pod with Jenny Cassin. She is author, she is an attorney, sorry, investor, capital raising coach, the owner of the casting group, and co founder at Opportunity Main Street. We're going to talk about a bunch of interesting topics today. How to raise capital, how to run a business, grow a business, that is. Jenny is also an author, by the way. Raise capital on your own terms. I knew I wasn't wrong on that one. This pod is presented to you by pod.com if you want to start your own podcast and scale it, you're going to go to podb.com Jenny is live from Oakland, California and I am live from Oaxaca, Mexico today. Jenny, welcome to Pond. Tell me a bit more about yourself and about what you're up to nowadays.
Yes, well, thanks for having me. So since 2006, I've been an attorney working in the space of helping businesses raise capital. And what I specialize in is all of those businesses, which I would say is maybe 99% of businesses that are not a good fit for the venture capital model. So it could be, you know, a retail business, a bricks and mortar business, a manufacturing business. It could even be a tech company that has the potential to grow big, but does not want money from venture capitalists because they don't like the model. And the model with venture capital, as probably a lot of your watchers know, is that they want to invest in a business that's going to grow very fast and then have some kind of a big exit. So an IPO or a sale of the company. And a lot of company founders really don't want to be forced to make an exit their top priority. They're more interested in growing the business in a healthy way, you know, maybe not having to focus solely on how do we become an attractive acquisition target. So those are the kinds of businesses that I help to raise capital. And we do it by using investment tools that are outside of that mainstream VC approach. So we create totally different kinds of term sheets. We customize the term sheets to their particular situation and then we go out and find investors that are open into those more creative terms.
What can be those creative terms? Give me a couple of examples here.
Yeah, so I mean, there's lots and lots of options. One option that's becoming more and more popular is something called revenue based financing. And this is where. And you can do revenue based financing in the form of either equity or debt. So if it's debt, it's a loan where the payback is you make annual payments or quarterly payments to your Investors based on your usually top line revenues and you keep paying them until they've reached some multiple of of what they originally invested. So that's becoming more popular when you're talking about revenue based equity. That's where they invest in equity and you can buy back the equity at a certain pre agreed valuation. So those are a couple examples. There's also equity of other kinds where they might invest in equity and maybe there isn't revenue sharing, but there's dividends. And there's another type of exit based on something that happens in the future. Like when we hit a certain revenue goal, we have the optionality to buy to have the investors redeem their equity. So there's lots and lots of options and possibilities. Really I'd say, I always say there's really an infinite number of, of terms that you can create for your investors.
How did you get to where you are today? You started your own law firm, you were the president of Sustainable Business Alliance, Sustainable Economies Law Center. You also work for the city of Fremont. You have a unique background. How did you get to where you are today? What's your story?
Yeah, so I mean I've always been kind of an activist trying to make the world a better place in one way or another. And after law school I went and worked at a nonprofit. I stayed there for 11 years and it was a community development nonprofit in Oakland. And what we did is we did all kinds of things to improve this low income community. So we built a big real estate project. I worked a lot with the small businesses to help them be more successful. And in doing that work, I just became really, really passionate about small business. I feel like small business is such an important factor in the success of a community and a society. So I just wanted to do everything I could to support small business businesses. And I saw how they were struggling and if they only had sufficient financial resources, they could be a lot more successful. They could pay their workers well. They could not have to work 80 hours a week. You know. And so I just started to look into why is it that there is such a lack of capital for most businesses? Apparently from What I've heard, 83% of businesses in the US don't have access to bank financing or venture capital style funding. So it's like a huge number of businesses that just have, you know, they don't know how they can possibly get funding. They're always under resourced in terms of money. And so I just started to try to figure out what can I do to try to address this problem. So that's how I, I co founded a law firm to address the problem in 2006 and then in 2015 I went off on my own and started my own law firm. And I also work on a lot of projects to kind of build the ecosystem of this type of investing. So right now I'm working on a project in Baltimore, Maryland where we're going to have, we bought a building. And that building is going to serve as a place where we can support entrepreneurs who are raising funds and also invite the community in and help the community invest in those businesses via a platform that we have called Crowdfund.
Baltimore.com is crowdfunding still, well, nowadays is it still a good option for most startups?
I think crowdfunding can be a really great tool. You know, in the US we got this law passed in 2016. I was involved in advocating for the passage of that law. I mean it was actually passed in 2012, but it didn't go into effect until 2016 and, and it has it. The law itself has some challenges to it. That can be frustrating. But the fact that you can as a company in the US whether you're a brand new startup or you know, a going concern, you can raise money from investors, you can offer anything you want, equity, debt, convertible note, whatever, safe. And you can offer it to everyone in the entire country. The minimum investment can be very low. So it's an amazing tool. You know, it doesn't always work out. It's not. Some people think they just stick their offering up on a platform and they get funded and it doesn't happen that way. It's a lot of work. But I definitely am a big believer in the tool and I love the fact that it creates the ability for regular folks in the US and potentially people outside of the US too can also invest in US companies to invest in small businesses and not have all of their money that they have invested invested in big giant multinational corporations that are traded on in the public markets.
Who are your ideal clients as startups that want to raise in creative ways? Because I guess it would be startups that probably like aren't going for the big exit. Like not potential unicorns or people that have been refused by classic Silicon Valley vc. Like who's your ideal startup?
Yeah, I mean it's really anyone who either isn't a fit for venture capital or who doesn't like the venture capital model. And ideally it's a business that has an appeal beyond just its ability to make money for its investors. I like to work with businesses that want to have a positive impact on the world. So in addition to being financially successful, they want to do something that's going to create positive impact, like maybe treat their workers really well, do things for their customers that other companies don't do. Like for example, you know, a lot of venture backed tech companies are kind, you know, sometimes take advantage of their customers, sell their data, et cetera. But a lot of my clients that are tech companies, they pledge to their customers, like we won't do that to your data because we don't have investors that are going to force us to do that. You know, maybe they give back to the community by giving to a lot, giving to charity. Maybe they are a very environmentally friendly business that is, you know, helping to solve the problem of global warming. You know, so those are the kinds of businesses I love to work with because oftentimes it's easier for them to find investors because believe it or not, the vast majority of investors in the US want to invest their money in alignment with their values in companies that are making a positive change. So it makes it a lot easier to raise money if in addition to having a, you know, a business plan that's going to be, you know, that shows you're going to be successful, that you also are going to have a positive impact.
There you go. And who would be the ideal Persona on the VC side? Would it be an angel investor? Would it be a private equity person or just a high net worth individual?
Yeah, so when it comes to the investors that we tend to focus on, we call them not the usual suspects. We call them, quote, unquote, non professional investors. People that don't necessarily have preconceived ideas about what an investment should look like. People who are more open minded. Also, if people are not investing other people's money but investing their own money, they tend to be a better fit. Because once you're investing other people's money, you really don't have a lot of flexibility. Like it's all your model is already baked in. You've made certain promises to your investors, so you kind of have to do, you know, you generally you're going to be looking for the next unicorn. But if you're an individual, whether you're high net worth or not, you know, even if you only have like a few hundred dollars to invest, or maybe you are high net worth and you want to invest a lot more than that. If you see the value in diversifying and not putting all of your money into the same type of business with the Same type of model. Those are the investors that tend to be excited. So just as an example, I'm raising money right now for this project I'm working on in Baltimore. We have about 30 investors. The check sizes have been as small as $10,000 and as large as 200,000. We've raised a total about 1.7 million. But every one of our investors is an individual, a family, a small business. There's one foundation, but other than that, it's all. And they're all accredited investors. In our case, we're only raising from accredited investors, but those are the folks that we find tend to be the best fit for this model. There's sometimes every now and then we will find a more institutional type of investor, like a foundation or you know, maybe some kind of an impact investing organization that will also come in.
What is your model on your side? Like what fees do you take from helping these startups or these investors invest their money in alternative ways?
Yeah, so from my law firm side, I take, I, I charge fees for my services, usually a flat fee. So we, you know, we just, we don't love the hourly model that a lot of lawyers use. So we usually charge a flat fee to help people do this. And then on the crowdfunding side, we take a percentage of the raise. Like we have crowdfund baltimore.com, we also have crowdfundmontana.com, crowdfundmainstreet.com and we'll probably have more geographically specific and community specific sites coming soon. We love partnering with communities to set up, you know, geographically or, you know, value specific websites that, where they, where people in their community can, can invest in what they care about.
There you go. And what would be your top goals for this year?
So I really hope to complete the project in Baltimore that I've been working on for a while. Our building is halfway renovated. We are looking for investors, accredited investors. So we still need to raise a bit more to complete the project. And if we could open that in Baltimore and show that it is actually going to work to move more money from local residents into investing in local businesses, we do hope to start looking at taking that model to other communities throughout the country and maybe even the world.
Love that. And what challenges do you think will be in your path? What challenges will you cross into the accomplishment of these goals?
Yeah, I mean, just like any founder, you know, there, it's very challenging to do run a business. This business is really a real estate business. We're going to be leasing out space in the building in order to pay the costs of running the building. And so we, you know, obviously there's the challenge of raising the balance of what we make need to raise. We've raised like I said about 1.7 million but we still need to raise more. It's a very old building. So guess what, it turns out the renovation costs were higher than we thought they would be. And so the challenge of raising the money of course and then once it's operating just making sure that we have the revenues coming in that we are are hoping to and you know, getting the right people to to lease the space. So just like any founder, those are the challenges that going to be facing.
Right. Where can people find out more about you online? Jen?
Yeah. So my law firm website is Jenny casson.com and my Baltimore project is opportunity main street.com and then we also have crowdfund baltimore.com.
