The Business Gay Podcast with Host Calan Breckon
The Business Gay
VC and Angel Investing for Startups
VC and Angel Investing for Startups with Swish Goswami

In this episode of The Business Gay Podcast, host Calan Breckon speaks with entrepreneur, Swish Goswami.

Swish is the heart and soul behind Surf, a loyalty platform shaping ethical consumer connections and data collection. As CEO, Swish has woven Surf into the fabric of internet browsing and worked with giants like Netflix and Amazon Prime Gaming, raising over $8M and sealing two impactful acquisitions. Beyond the boardroom, he co-founded the “Track Limits Podcast,” all about Formula 1 racing. Swish is an accomplished author, K-Swiss ambassador, League of Innovators Board Chair, and passionately helps guide organizations through his angel fund AGEX Capital.

His journey is studded with accolades like Startup Canada’s Young Entrepreneur, LinkedIn Top Voice, and Plan Canada’s Top 20 under 20. Beyond the titles, Swish is a storyteller at heart. He’s shared his wisdom on TEDx stages 4 times and taken part in over 300 global events, making entrepreneurship a deeply personal voyage for Swish.

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Key Takeaways for quick navigation:

  • [01:52] Angel Investing involves individual funding, while Venture Capital consolidates funds into a separate entity with a general partner and limited partners.
  • [02:34] Swish shares raising $750,000 from 21 Angel Investors for Surf in 2018.
  • [03:29] Building relationships before asking for money helps in fundraising; feedback and implementation build trust with potential investors.
  • [05:10] Founders should be prepared with a data room, financials, deck, and product demo when seeking investment.
  • [06:44] Swish advises delaying fundraising if possible, allowing time for bootstrapping to mature the product and metrics, potentially increasing valuation.
  • [09:45] Founders should establish a clear timeline, inquire about the investor’s thesis, and seek information on how the VC supports portfolio companies.
  • [11:35] When selecting investors, Swish prioritizes those who are hands-on, have a good reputation, and can provide long-term value beyond immediate needs.
  • [13:40] As an angel investor, Swish looks for founders with compelling stories, evaluates market potential, and assesses whether the product is personally appealing and makes sense.
  • [15:02] Swish explains different exit scenarios: IPO, sale to another company, and mergers, emphasizing the need to consider what is best for the team, investors, and oneself.
  • [17:47] Swish acknowledges market fluctuations and advises founders to prioritize the well-being of the team and investors when considering exits.
  • [19:22] Surf compensates users for their data and is in an M&A process. Swish gears up for a new chapter in gaming, joining as the Head of Growth.


[00:00:00] Calan Breckon: Today’s episode is sponsored by Convertkit, the email marketing platform for creators. Now I use Convertkit and I’ve been using Convertkit for years because I found it was the most efficient and easy to use out of all the email service providers. And I’m a super efficient person, like efficiency is one of my core values, so it was a natural fit. Convertkit simplifies your email marketing by combining powerful automations with an easy to use interface. I love using the visual automation builder because I’m a very visual person and it helps me to organize all my automations in a super simple and easy way. Automations are SEO important as a solo entrepreneur because it saves you so much time to just be able to set it and forget it. And with Convertkit’s automations, you’ll never have to worry again about your email delivery. When you create a sequence in Convertkit, it’s easy to switch between emails and editing in a single window, no pausing the sequence or clicking in and out of multiple pages in order to make changes. This is really important because I know some super annoying providers that once you set a sequence, you have to pause it in order to edit it. But then what happens if somebody signs up while you’re editing it? It just makes no sense. Convertkit doesn’t do this to you and it’s magical. ConvertKit also integrates with all of your favorite e commerce platforms, lead generation services and membership sites. I use mine with thrivecart and my website and loads of other programs. Now the best part about Convertkit is that they run on a sliding scale payment system so you can get started for as little as $9 a month when you learn all about its systems and how to grow your email list. And then as your email list grows, you will slowly go up in cost. But to start off with, it’s super affordable. You can get started with Convertkit today by heading over to or clicking in the link in the show notes. Now, before I jump into today’s episode, I just want to ask that you hit that subscribe button to show your love and support on whatever platform you’re listening from. Now, let’s jump into today’s episode.

Welcome to The Business Gay podcast where we talk about all things business, marketing and entrepreneurship. I’m your host, Calan Breckon, and on today’s episode, I have entrepreneur Swish Goswami. Swish is the heart and soul behind Surf, a loyalty platform shaping ethical consumer connections and data collection. As CEO, Swish has woven surf into the fabric of Internet browsing and working with giants like Netflix and Amazon Prime Gaming, raising over $8 million and sealing two impactful acquisitions. Beyond the boardroom, he cofounded the “Track Limits podcast,” all about Formula one racing. Swish is an accomplished author, K Swiss ambassador, League of Innovators board chair and passionately helps guide organizations through his angel fund, AGEX Capital. His journey is studded with accolades like Startup Canada’s youth entrepreneur, LinkedIn, top voice and plan, Canada’s top 20 under 20. Beyond the titles, Swish is a storyteller at heart. He’s shared his wisdom on TEDx stages four times and taken part in over 300 global events, making entrepreneurship a deeply personal voyage for Swish. I’m very excited to jump into VC and angel investing with Swish on today’s episode. So let’s jump in.

[00:03:20] Calan Breckon: Hey Swish, thank you so much for taking the time to be on the podcast today. How are you doing?

[00:03:25] Swish Goswami: Doing well. Thanks for having me. It’s a sunny day in Toronto. I’m very happy about that. But otherwise things have been good.

[00:03:31] Calan Breckon: Yeah, awesome. I have to agree. I’m looking outside my window right now and it’s a beautiful blue sky and I’m like, yes, come on, spring.

[00:03:39] Swish Goswami: I know, I can’t wait for it. Spring is typically my favorite season of the year as well. My birthday is in spring, so a lot of things to look forward to.

[00:03:47] Calan Breckon: Oh, nice. Happy early birthday.

[00:03:49] Swish Goswami: Thank you.

[00:03:50] Calan Breckon: Cool. So I want to jump right into things and we’re going to get right to it. I’m really excited. What is the difference between angel investors and venture capital?

[00:04:00] Swish Goswami: Yeah, great question. So with angel investing, you’re typically taking money that you have on your own as an individual and you’re funding companies with that. With venture capital, you’re kind of consolidating funds together, building a separate entity where you have a general partner and you have limited partners below that general partner that are all contributing to the fund.

The cool thing about angel investing is that if you make a return, so for example, you invest in a company that imagine they raise their first round at a four or $5 million valuation, they end up exiting on a 50 million valuation. So technically you ten x your money, you’re going to get that entirely to yourself. Versus with a venture fund, they obviously have a carry arrangement where you basically divvy up the profits from fund one, let’s say, and you would divvy it up based on what people initially put in. So their kind of contribution to the overall fund. So yeah, a VC is pretty much the difference between doing something in an individual context versus doing it as part of a team with a broader entity and a broader structure.

[00:05:05] Calan Breckon: Okay, awesome. Thank you very much for the depth on that. Can you maybe share a little bit about the first time you ever went to maybe ask somebody for money in terms of whether it was an angel or VC and how that played out for you?

[00:05:19] Swish Goswami: Yeah, 100%. This would have been back in 2018 when I was raising money for surf, previously called True Fan. We did a precede round of about 750,000. We raised it from about 21, 22 angel investors. So we didn’t actually go to a fund or a family office. We went to a bunch of individuals that were high net worth, and we asked them for 10,000, $25,000 each for high net worth people. That’s not typically a lot of money.

So for them, it was a drop in the bucket. But obviously, a lot of these angels that I also talked to were people that I’d be talking to since 2015, 2016.

It was definitely intimidating, though, because at the time, I was 20 years old, and it was definitely the first company that I was raising money for and kind of the first company that I was even taking the helm of being CEO for.

So I obviously had a lot of imposter syndrome when I was raising money. How do I pitch? How do I follow up with people? How much pressure do I put on them? How do I create fomo? These were all things that I had to learn and candidly learned a lot through mistakes, but being able to get that round done and then subsequently, then being able to do two more rounds after that, where we did raise from institutions, it’s taught me a lot about fundraising that I can apply, obviously, going forward.

[00:06:41] Calan Breckon: Nice. So taking that a little bit deeper, what was really going through your mind kind of that first time or the first couple of times? And how did you bring up the, hi, I would like your money, please.

[00:06:52] Swish Goswami: Yeah. The way I mainly did it is building a relationship with a lot of these people beforehand. So the way I met a lot of these angels that came on board was by interviewing them. In 2015 and 2016, I wrote a lot on LinkedIn. I had an article series, hashtag Unconventional, where I wrote articles on high net worth, successful people that I looked up to, and after interviewing them, I followed up with them. I built a relationship with them. I reached out from time to time saying, how can I help? I connected them to other people. So even before I decided to go and make that ask about, hey, I’m building this company, and I’m raising money. Are you interested? I already had, like one to two years of experience working with a lot of these people in terms of helping them out, answering questions, updating them about my life, updating them about ideas. I was thinking about asking them a bunch of questions to make sure that they knew who I was.

When I did eventually go and make the ask, though, definitely. It’s scary. Typically you do it over email or you do it on a phone call. And the way normally to do it is by also first getting feedback on your idea. Because it’s always good to be able to pitch the idea, ask them what they think, factor in their feedback, and now when you feel like, okay, you’ve acted upon their feedback, it’s a lot easier to go back to them and say, you had some great advice for me. I actually implemented that. I’m actually raising money now. Are you interested in coming on board? And it kind of makes the ask a little bit better and not just out of nowhere. So that’s how I did it.

Again, I think you have to realize at the end of the day that if you go to people and you’re asking them for money, you need to be prepared. So from my end, having a data room ready with financials, having my deck ready, having a product demo ready, being very available to answer questions over a Zoom call in person or over email, that’s everything that I needed to do on my end to make sure that I knew that I was fully ready to take on capital and do it in a very quick way.

[00:08:52] Calan Breckon: Nice.

Now that you’ve been invested in and you’ve been investing yourself, are there any tips or advice that you can share with startup founders that maybe are red flags that you’ve seen or pitfalls that folks might fall into if they’re early stage or never done it before that you learned for yourself?

[00:09:15] Swish Goswami: Yeah. Two things that come to mind. Number one is you don’t need to fundraise to build a business. I wish I knew that a bit earlier, because I think for me, when it came to building a business, I rushed into fundraising because it was the easy way for me. I built up this network, I had access to capital, I immediately went for it. Versus had I known that, hey, you could actually spend six, seven more months just bootstrapping and not raising money, not giving up any sort of equity, continuing to get your product more mature, continuing to get more customers to test it out, get more feedback, sign more letters of intent. I think that would have been great because that early valuation that we raised on could have actually been four or 5 million more. Had I had more, Lois, had I had more of a mature product than I pitched on initially. That’s number one, is try to delay the process of fundraising to as late as possible.

Obviously, be responsible. Like, don’t keep it to the very last day. But if you can try to extend not fundraising, and you can continue to bootstrap and continue to show more mature metrics, you will put yourself in a better situation when it comes to fundraising. The second thing is, it is a numbers game. At the end of the day, for every one person that said yes to me in the last five years, I probably had like 50 to 60 people that said no. I actually have a database from every single round that we’ve done, and the vast majority of the Excel sheet is a bunch of red rows. Red meaning people that just said no. So you have to be ready to take on rejection. I think early on when people said no, I’d always be like, that’s bullshit, how could you say no? And I take it more personally, versus later on, you kind of figure out that it’s not personal. And a lot of times, by the way, sometimes people just don’t have the bandwidth to invest in you. They have other priorities. The fund that you might be talking to might not actually be interested in your space, but they might like you, and they might want to stay in touch with you, and you need to know that. So that’s where I think being a little bit more mature now, you kind of realize that every single no is definitely an opportunity for feedback. Not every piece of feedback needs to be acted upon, but it’s always good to know that it’s never personal when someone says no, or typically never personal.

[00:11:29] Calan Breckon: I just want some clarification around fundraising. So you said bootstrapping is really great, and I agree. I think you can bootstrap a little bit longer. Do you include that as fundraising is kind of your seed and a rounds, but maybe the friends and family is included in not really fundraising, but still getting money in to help you. And how do you differentiate that?

[00:11:51] Swish Goswami: I still count the friends and family into fundraising because for us, that’s what we call precede. Right? Precede is typically you go to your friends, family members, you might even crowdfund. And then seed is obviously you’re tacking on institutions series aid. You’re probably exclusively raising from institutions at that volume.

So, yeah, for me, I think when I say bootstrap for as long as possible, I mean, if you have the bandwidth to be able to do that. And again, everyone’s different. Some people might not have the financial means to do that. Then you might need to fundraise a bit quicker. But if you do have the financial means to extend, not fundraising for, let’s say, four or five more months, and you have a path to get more mature metrics, whether it is a more mature version of your product, or whether it is four or five more customer letter of intent, or whether it is being able to bring on a kick ass superstar employee that you think when you put their name in the deck and when you get investors in front of them, they’re going to do a great job. Maybe it’s worth waiting a bit longer.

[00:12:50] Calan Breckon: Nice. Are there any questions that early stage founders need to be asking during these kinds of conversations that maybe they wouldn’t be thinking of, but you’re like, oh, no, this is something I learned. You need to ask this upfront.

[00:13:05] Swish Goswami: Yeah. Whenever you talk to an investor, even if it’s an angel or an institution, you should be clear on a few things. Number one, you should be clear on timeline. You should have a timeline in mind about when you want to close the round. The worst thing you can possibly do is keep yourself in limbo. And by keep yourself in limbo, I also mean not convey a very clear timeline to an investor, which makes them think that, oh, I have all the time in the world to make a decision, when in actuality, they probably should give you an answer within two to three weeks.

So that’s always good. Is giving a very firm deadline on here. We’re fundraising, we’re actively doing this. We’re looking to close around in about a month and a half. We’d love to get an answer from you in two weeks, or we’d love to get an answer from you in three weeks and try to put that sort of timeline on someone. The second thing is definitely, if you’re talking to a fund, you should ask them about their thesis. Hey, in 2024, what are some of the core categories that you guys are investing in? You should also ask them after your pitch. What did you really like about my pitch and what are you not fully convinced about? You can ask those types of questions and they’re actually really good to potentially indicate to you what you need to double down on in your follow up email to explain a bit further in case there are areas that they’re not fully convinced on that are important to your business. And then the final thing to definitely ask is specifically when it comes to follow on investment, I think it’s always good to ask a fund, especially if you’re talking again to an institution, how do they support portfolio companies? If I do become a portfolio company of x fund beyond capital, what sort of value can you guys provide us? And it starts to get the VC thinking that, oh, this is an entrepreneur that wants not just money, but they want development in other areas. And that’s very attractive to a lot of vcs.

[00:14:52] Calan Breckon: Nice. Did you have any set rules when it came to investors, when you were looking for your company that served you really well?

[00:15:00] Swish Goswami: Yeah, I think one, we wanted to make sure we found people early on that were hands on, a little bit more like if we call them, if we email them, they were going to respond on time. They were responsible.

I wanted to also try to find people that had a good reputation.

So there were definitely conversations that we’ve had in the last five, five and a half years where we’d talk to an investor, they’d talk a big game, and then we’d go and talk to some of the other people that we looked up to, either on our board or advisors, and they’d be like, stay away from that person. They’re a bit shady.

So we wanted to make sure that whoever we brought on kind of went through a little bit of a sniff test with our board and also some of our core advisors that we constantly were talking to. And then the final thing is we wanted to make sure that we found someone that could provide us value in the future. So whether that was opening up a new customer segment, helping us with marketing, helping us with hiring, helping us with future fundraising rounds, we wanted to make sure that the value that someone brought wasn’t just immediate, like within the next three to four months, but within kind of even the next three to four years, we could still potentially extract value from that investor coming on.

[00:16:05] Calan Breckon: Nice. Now that you’re on the flip side. So we’ve been talking about how when you were doing the fundraising and when you were in that space, now you’re on the flip side. And I know that you do angel investing yourself. Do you have any kind of set rules that you have in motion for investments that you make with your angel investing?

[00:16:24] Swish Goswami: Yeah. The three things I think I typically look for is, number one, obviously the founder, is it someone who has a cool story? Do they have a very interesting background that lends themselves well to the business? So if they have a background that potentially gives them a unique advantage, like why they’re the ones that should start that business, that’s always a very good sign. The second thing is market potential, right? Like, is this a market that is likely going to continue to grow? Is it a market that potentially is going to become more and more dominant going forward, or is it potentially going to regress and then finally the product, does the product actually make sense? Would I use it? If I would use it, then great, that’s even better. And that’s why even with ship, for example, here in Toronto sauna Colonial, I’m there like twice a week with Brassa Peruvian. I eat their food like three to four times a week. I love being able to obviously put money towards projects that I can also benefit from directly and get value from, because I feel like, hey, if I like it, at least I’ll know. Some of my friends that are very much like me will probably like it as well.

[00:17:23] Calan Breckon: Yeah, that’s kind of the golden egg, right? If it’s like, not only are you creating something that solves problems for people out in the real world, but for the founders and the people themselves who are creating it, they’re like, I want this, I need this. And I see the huge value in it, which is why I’m investing so much of my time into creating this.

[00:17:41] Swish Goswami: Exactly.

And I think even when we were building surf out, we tried as much as possible when we were fundraising to ask questions like, oh, do you currently use chrome extension? Do you use honey? Do you use Grammarly? Because if an investor said, yeah, we do, actually, and we couldn’t do our job without it, we were like, oh, that’s cool. The fact that they are already using chrome extensions and now they might use surf is a really cool kind of green flag for us.

[00:18:07] Calan Breckon: Nice. I want to dive a little bit deeper now into kind of like later stage things to explain things to early stage founders. Can you explain a little bit more about what an exit is and what that really means for the business that was invested in? Because you hear exit all the time. But sometimes people don’t really understand what the actual concept of the exit, I.

[00:18:29] Swish Goswami: Mean, an exit can take in kind of multiple forms, right? So there’s obviously at the very top line an IPO, which can occur in some cases. So you can have a company that IPO is not only on a Nasdaq or a Toronto stock exchange, but there’s now actually micro cap stock exchanges as well. So like the Toronto Stock Exchange has TSXB, which stands for Toronto Stock Exchange venture, and that’s for companies that are typically below 100 million market cap. So when you ipo, it doesn’t have to be just immediately to the big leagues, it could be to a micro cap stock exchange where obviously the equity that you hold as an investor now is going to be put onto the public markets. And obviously there hopefully is an appreciation in the value of your equity immediately. Typically, there’s about a six month lockup period before you can actually take money out when a company goes public. And after that six month lockup period, you can buy more, you can sell, you can do whatever you want because you obviously hold stock in a public company similar to holding stock in an Amazon or Facebook or whatever. So that’s, number one is IPO. The second is obviously a sale to another company. That’s typically the most common when people go through the exit process and they’re looking for selling directly to a competitor or to a bigger company in their space.

Typically an investor has the option of cashing out right away if the sale price is obviously higher than what they invested in, or they also have the option at times to carry on. So sometimes a sale occurs with no cash and all equity, in which case an investor has the ability now to gain equity in the new entity or the company that is acquiring the original company. You can gain equity in that acquiring company and obviously continue the journey from there. The final part of an exit is a merger.

You don’t typically see mergers occur too often, I feel, in Canada, but they do definitely occur. But a merger, obviously you have two companies. Maybe one of them is not significantly bigger or significantly smaller than the other. So sale might not make sense, but potentially a merger would make sense. So you bring the team together, you bring the two entities together, you create a new entity, and then the investors kind of fold into this new entity as well.

So, yeah, there’s three different scenarios and all have their pros and cons.

Public markets, for example, in the last, maybe year and a half, probably not the most ideal thing to go and IPo, but back in 2020 and in 2019 is probably the greatest thing you could have done, is try to push for an IPO. So there’s always ebbs and flows when it comes to what’s ideal from an exit point of view. But the biggest thing is to note that if you are considering it, you need to do well not only by yourself, but by your team and by your investors. That’s always the kind of three considerations that a founder should have.

[00:21:19] Calan Breckon: Yeah, and there’s always ebbs and flows with the market. It runs on trends, and sometimes we’re up, sometimes we’re going down. And right now it looks like it’s on kind of a downward trajectory, but that’s okay. There’s been many a big unicorn company that was actually created during those downtimes, because I believe that pressure creates you to run leaner, which just creates you to create more of an efficient business model.

[00:21:43] Swish Goswami: Definitely agree. I mean, every single company today is talking about profitability, right? And that’s not necessarily the conversation three or four years ago, but it’s good because even startups have to focus on that. And the faster they get to that stage, the better off they’re going to be coming out of this period.

[00:21:57] Calan Breckon: Definitely, yeah. With the mass adoption of AI and AI technologies, it’s become the year of efficiencies. It’s like last year and continuing on through this year is the year of efficiencies. Is there any questions that I haven’t asked yet through this conversation that I should have asked?

[00:22:17] Swish Goswami: Not really. I think you’ve done a great job of exploring fundraising and exits and investing, both on, obviously the founder’s perspective and the angel perspective. So, no, I think you’re doing great.

[00:22:28] Calan Breckon: So, cool.

Let’s finish off with a little bit of info on surf. Can you share what surf is and what you’re working on now?

[00:22:37] Swish Goswami: Sure. Yeah. So surf is a company started about five and a half years ago, compensating people for their data. So people right now share their data on Google and Amazon and Facebook, but you get absolutely nothing back except for personalized advertising, which we all love.

So we built a platform, a Chrome extension. It operates on other browsers as well. You can download it, you can give your data anonymously as well as passively, and we will compensate you directly for it. So you’ll get points which you can then use for items and gift cards and discounts. We take the anonymized data that we get from consumers, we share that directly with companies. And along with that, we also give them access to a platform to run giveaways and provide discounts in a very meaningful and actionable way.

With surf right now, we are engaged in an M A process and being very much heads down on that. While I’m doing that, I’m also kind of gearing up for the next chapter of my life, which is going to be within gaming. So coming on as the head of growth for a gaming studio in Toronto called Parallel, which is very much engaged on trying to build the next Star wars, so they have this very cool piece of IP, cool story that they’re telling through comics that they’re releasing each month, collectibles that they’re releasing each month and they also have a very cool trading card game to go along with that. So we’re trying to tell a story that is different. We’re trying to tell something that’s fresh, but we’re trying to inspire kind of the next generation of Sci-Fi fans that maybe haven’t had anything new in the last 1015 years.

[00:24:11] Calan Breckon: Nice. I love all that. I’m a giant Sci-Fi nerd. Like anything Sci-Fi I have watched all of it, taken part in all of it.

We’ll have to dig more deeper into that.

[00:24:22] Swish Goswami: Absolutely. Definitely. Check it out. Parallel life. It’s a super bold project and the team itself, they all come from a crazy background. We have artists and animators and game developers that worked at Activision, that worked on big movies under Paramount, under Warner Bros. So it’s an all star team put together and it’s pretty great to be able to see that they’re going after a very big mission and they are canadian as well.

[00:24:47] Calan Breckon: Nice. Yeah, I love the homemade homegrown Canadian made where can folks find out more about surf

[00:24:55] Swish Goswami: So you can go to if you want to download the extension slash extension and you can directly download it there.

[00:25:03] Calan Breckon: Awesome. Well thank you so much. This has been a great insight into fundraising, angel investing vcs. Thanks so much for your time. Swish.

[00:25:12] Swish Goswami: No worries. Thanks Calan.

[00:25:14] Calan Breckon: I hope you got a lot out of today’s chat, I know I did, and I want to thank you again for tuning in today. Don’t forget to hit that like and subscribe button. And if you really enjoyed today’s episode, please consider giving it a star rating. The Business Gay podcast is written, produced and edited by me, Calan Breckon and if you’re looking to get some SEO advice, you can head on over to or just click the link in the show notes. That’s it for today. Peace, love, rainbows.

Calan Breckon
Calan Breckon

Calan Breckon is an SEO Specialist and host of "The Business Gay" podcast. He has worked with companies such as Cohere and Canada Life and has been a guest on the "Online Marketing Made Easy" podcast with Amy Porterfield as well as featured in publications like Authority Magazine and CourseMethod.

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