The Exchanges

Q Interesting. I guess close out the Bloom Nation story before we dive deeper into Whitby. So how much did you raise there and what, what was the end story there? What happened?

A Yeah. So we raised about twenty million. I actually departed. I was a co-founder in CRO and I think just decided after six or seven years wanted to start something else. So I left, both my co-founders are there. I think they raised around after I left. Um, so yeah, it's still there. It's still intact. I believe it's about a hundred people, uh, employees when I last checked. But I think the one thing for me is I wanted to build something a little bit differently, bootstrapped. There was two things I wanted to do, not raise money so I could decide my own fate and how I wanted to do so. Um, and secondly, the addressable market size. I think we were really specialized in the florists and I think Bloom Nation, as I was leaving or after I was trying to get in other industries, but that was difficult. I think here we started with something super broad, like communication, and then we narrowly defined the use case, which was challenging in itself to start, but I think allows it to scale, scale user without like hitting, hitting roofs or hitting a small, small industry. Um, but yeah, the company's still there and, uh, excited to see them continue to grow.

AI assessment note: “we raised about twenty million. I actually departed. I was a co-founder in CRO”

Q I do think that founders, you know, VC money is, I think, the best marketed money in the world. And for everyone that raises, there's a thousand that are profitable, happily bootstrapping at five million run rate. You have the foresight or, you know, just the site in general, but basically have both, you've seen both worlds. What advice would you give to someone today looking at raising versus not?

A I think the best thing I've ever heard someone say is optionality. So it's like, if you don't raise, you have the option. You can do it on your terms. You don't look needy. So I compared a lot to going to a bar and talks about, you don't need to meet anyone. And generally things come to you. Um, like right now, I think I've had three or four emails in the last day, just on family offices, just looking. And when you don't need it, they want you more. I think that's, that's part of it. I think this, the second thing is just, I think, You can make poor decisions. I don't want to throw them under the bus, as you said, but when someone, um, starts a company, if someone gives them five million bucks, I think they make poor decisions. If the only way to hire people is through customers paying you on contracts, that means you have to actually build something that people want. You have to get a credit card and they have to pay you. So it's much more difficult to start. But I think once you get to like the, as you said, like the three to five million AR and you scale, You build product better. You make better decisions. You're much more culpable. Like even on sales and acquisition, you look at payback and you look like things that matter. You look at your P and L a lot. It's, it's, you actually act like someone like your dad, how he ran a business, right? But actually with new age techno…

AI assessment note: “if you don't raise, you have the option. You can do it on your terms.”

Q That makes sense. Real quick. Uh, how do you drive? People say you can't bootstrap and also drive crazy good growth. What do you, how are you going to drive?

A I think that's, that's a good question because in December, I presented this to the company. I think it's just different channels. So here's my first question for most of the listening, but it's like, what, what is the channel that people use? Let's just call for B to B sales. We started with outbound, which is different from a lot of people. Like we started because of blumination, again, a blessing of blumination, like cold calling, cold emailing, like true SDR and I was the AE. I think now we're starting to see inbound, but I think with our API, like partnerships, trade shows, outside sales, like inbound, like those channels that most people rely on in the beginning are things that we haven't even tapped yet. So I think partnerships will be a big thing because as we go to different systems and we Have mutual customers and they're missing stuff in their system, right? If you're at accounting, uh, CRM and you don't have this, this, and this, you can now use our API. You push people to us. Um, there, there could be like an affiliate rev share there. Um, that and white labeling stuff like that, I think would be a big part of the growth of the next 24 months.

AI assessment note: “I think with our API, like partnerships, trade shows, outside sales”

Q Yeah, I mean, all disclosure, I mean, you're not buying a hundred wind turbines you have to go install to start helping florists run their companies better, so it's not like it's capital intensive. I don't think so, unless I don't know about capital intensive at the start. Um, but look, lessons learned makes a lot of sense. I guess, what year did you leave? Was it 2016?

A No, no, no. I was, so, my kind of path, I'll just give you my path in a nutshell. It was like 2008, I won the World Series of Poker. 2010 to 12, I went to the University of Chicago for my MBA, and then we started in 2030. I left in right, right during COVID. So I'd been there, by the way, the company's been there. Company's actually been there for now for like, 10 years. Um, so, um, but I left, uh, in 2022 1019, 2020, and started this kind of in the midst of COVID. With some, again, and when we started, it wasn't exactly this idea. Myself and my partner were testing different ideas, but I think this really took hold at the end of 20, 20, 20, 21.

AI assessment note: “No, no, no. I was, so, my kind of path... I left in right, right during COVID.”

Q That makes sense. And you started onboarding customers in what year? When did you, how'd you get your first customer?

A Yeah. So the actual real first customers, and I don't know if they have the best Use cases for people, but it was just my old customers. So floors were some of the first, you look at retention, retention wasn't great. And I think the reason we realized is they were using it just for marketing. We saw high retention of people that use this for operations. Like if the platform came down, we'd get messages within one minute. Like I can't communicate with customers. So I think that started to happen about two, Two years ago, two and a half years ago. And the hardest part was just finding the use case. It was depressing. Like I, I come from a sales background, so making cold calls, walking into people. But eventually I think it was a couple of cold emails and sequences, getting databases, sending out sequences, looking at open rates, getting on demos. And then honestly, just customizing the software a little bit. Um, for that use case that, that helped a lot.

AI assessment note: “the actual real first customers... it was just my old customers.”

Q Let's say, would you land that deal? So some of you do have customers paying you more than a 100,000 dollars per year because you've got them paying for what? API costs. What's the utility base?

A Not API costs, but what happens is when, so the SMB, it's like, why should you use our platform over there? Another texting or automation platform for them, it's developer costs. So like if they were to build off Twilio, they would have to build a communication plan, Twilio build certain features, certain sets. And like, then it becomes like, can you, and the developers, even a team of 10 at a big, Company couldn't really build this and get this off. So if they have a specific pain point, that's where I think our, our, our API comes in. And then we also have happened to be integrated to all the different, what's called aggregators. So like we can increase deliverability to a certain degree. So when you put those two together in your large company, it's just not worth, it's better to buy than build. I would say.

AI assessment note: “Not API costs, but what happens is when, so the SMB, it's like,”