The D2Z Podcast

148 - Bootstrapping to SaaS Success

• Brandon Amoroso • Episode 148

Share episode

In this episode of The D2Z Podcast, Brandon Amoroso interviews Chris Brisson, founder and CEO of Sales Message, discussing his entrepreneurial journey, the importance of bootstrapping versus fundraising, the significance of co-founders, and how businesses can leverage SMS marketing effectively. Chris shares insights on building a team, integrating SMS into customer lifecycles, and best practices for SMS marketing, emphasizing the need for businesses to adapt to changing communication preferences.

Here's What You'll Learn:
❗Chris Brisson started his first business at 19, selling rims and tires on eBay.
❗He has always bootstrapped his companies, preferring to avoid investor cash.
❗Bootstrapping allows for more control and less pressure to grow quickly.
❗Finding the right co-founder is crucial for business success.
❗SMS can be integrated into every stage of the customer lifecycle.
❗Businesses should focus on generating leads through SMS and other channels.
❗Integrations with platforms like HubSpot enhance the value of SMS marketing.
❗Texting can be a powerful tool for two-way conversations with customers.
❗Every business should consider their phone number as an asset for lead generation.
❗Simple strategies like text-to-join can yield significant leads.

Timestamps:
00:00 Entrepreneurial Beginnings and Journey
03:02 Bootstrapping vs. Fundraising: A Personal Perspective
06:12 Building a Team: The Importance of Co-Founders
09:10 Leveraging SMS in Business: A B2B Perspective
12:07 Integrations and Customer Lifecycle Management
14:56 Best Practices and Use Cases for SMS Marketing

Chris Brisson:
Linkedin - https://www.linkedin.com/in/chrisbrisson/

SalesMsg:
Linkedin - https://www.linkedin.com/company/salesmsg/
Website - https://www.salesmessage.com/

Brandon Amoroso:
LinkedIn - https://www.linkedin.com/in/brandonamoroso/
Web - https://brandonamoroso.com/
Instagram - https://www.instagram.com/bamoroso11/
X - https://twitter.com/AmorosoBrandon
Scalis.ai - https://scalis.ai/

Speaker 1:

Hey everyone, thanks for tuning in to D2Z, a podcast about using the Gen Z mindset to grow your business. I'm Gen Z entrepreneur Brandon Amoroso, the former founder of Electric and now the co-founder of Scaleless, and today I'm talking with Chris Brisson, who's the founder and CEO at Sales Message, which is a simple, secure and scalable business texting software. Thanks for coming on the show.

Speaker 2:

Yeah, thanks for having me, brandon, excited to be here.

Speaker 1:

So Thanks for coming on the show. Yeah, thanks for having me. Brandon Excited to be here. So before we dive into things, can you give everybody just a quick background on yourself and your entrepreneurial journey?

Speaker 2:

Yep, quick story. I got started young, so my first business I started when I was 19. So I sold rims and tires on eBay and built that business up. It was sort of my first e-commerce business. If you were to say that this is 2002. So it was a long, long time ago and, yeah, built that business up, ended up selling that in 2005. Vowed never again to sell physical stuff and so went into just learning everything I could about copywriting, you know, creating courses, writing books, writing eBooks, doing product launch, consulting and then really just fell in love with software. So built a couple of products throughout that time period, started a company in 2010 called Call Loop, which still exists today. That's in the messaging space. So calling, outbound textings, marketing, and then spun out sales message in about 2017, 2018 and um, yeah, so sales message, you know, is your conversational texting business texting platform, calling texting focused on really on the messaging side. Um, and yeah, and helping companies use sm SMS as a way to engage leads, qualify leads, capture them, convert them, you know, drive revenue through SMS.

Speaker 1:

How have you gone about the funding aspect of all these businesses you've started, have you primarily bootstrapped, or have you gone the fundraising path at all? You've started, have you primarily?

Speaker 2:

bootstrapped, or have you gone the fundraising path at all? Bootstrapped them all? Every company I started I bootstrapped, I think you know I was talking about it with my wife the other day man, I think I invested maybe $5,000 in sales message. So you know, today it's a, you know, multi, multimillion dollar company and so it's always been bootstrapped. I did raise $90,000 for Call Loop. This is back in 2012.

Speaker 2:

And I never felt good about that. I always felt that it definitely changed things and so my relationships I have with my two investors, the guilt I had about not growing fast enough. So I've always leaned away from taking on investor cash just because I don't know. It changed everything and you know I always wanted to perform and go above and beyond when things weren't working out or where they were working out. It was a little bit weird but yeah, I always bootstrapped everything.

Speaker 2:

Sales message was pretty much bootstrapped, call loop bootstrap for the most part, but every, every company I've started, I've always bootstrapped. I did try and raise money and learn very quickly. You know this is years and years ago. It didn't have that billion dollar exit opportunity and it was a good exercise for sure. I went to like San Francisco and did the whole round, did all that thing. I'm like you know what. I actually don't want to do this. So, yeah, I think even today, you know, I've been playing with lovable and replet and building out some just apps that have been on my mind for a long time, things that solve like little micro problems for me and internally, within sales message, you can bootstrap a company pretty quickly for nothing and get to profitability very quickly.

Speaker 1:

Yeah, I think the trend in 2025 is for founders to go that path, whereas right during the COVID heyday, you know, people are raising money left and right and I think there's a lot of businesses to your point who maybe went the fundraising route. That would have been better served bootstrapping because they don't have. It's just not a billion dollar opportunity business. There isn't anything wrong with that. It's just not a billion dollar opportunity business. There isn't anything wrong with that. It's just not set up to go the funding path.

Speaker 2:

Yeah, yeah, yeah. And in most cases, you know, I have some friends like I'm going to go and raise money. I'm like, well, one, let's even see if your business is investable. And in most cases the business is either a service business or a consulting business. It's just not investable. So no investor is going to want to invest in that because it's built around you and your knowledge and your skill set. It's not going to get a big return for them. So you know, I think most companies that may think they need to go and raise cash actually are not even investable to begin with and they may waste a lot of time, a lot of cycles coming to find out you should have just been selling, you should have just been generating revenue the whole time. So I'm not a big proponent of it Because, again, I think you can build a great company without that.

Speaker 1:

How do you balance, then, managing your cash flows and growing and scaling a business without being able to hire prematurely? You really have to be super dialed in on when you can start to bring in new team members. How have you gone about managing that for Sales Message?

Speaker 2:

Yeah, fortunately, when I started Sales Message, you know, I had another business that was generating like personal income and so that kept me afloat. And so, funny enough, you know, I looked at um, we use just works for payments and everything, and come to find out, um, wow, I didn't pay myself for like three, three, almost four years. And uh, I was like Holy crap. And I think I went into that saying, hey, I want to be able to build this business, not, um, killing my dogs. I remember I sold my one of my companies years and years ago and the guy that bought it he's like you know you want know why you couldn't ever grow this business. It was a a course, it was a credit repair course I created because I had bad credit back in the day. And he's like you know, you want you know why the business never really grew is because you ate your dogs. Essentially, you ate all the profit out of the company and you couldn't really reinvest in building it.

Speaker 2:

So with sales message, you know, I took a different approach, which was I don't want to take any cash out of the business, I want to continue to invest and build that out. And so you know, when you're building a software company, the biggest expense is people and development. And so being able to, you know, work with a co-founder, work with somebody that is skin in the game, that either A can take a discount in exchange for equity or, you know, they're just, they're part of the journey in the beginning and they're able to build, and you're able to sort of build Like I'm not a developer, I'm not a coder, I'm very technical, but you know, when it comes to building a product, I can't do that. So I always had to find a co-founder in order to sort of build up those businesses.

Speaker 2:

So, you know, I think there comes a certain point where, like early on, I was doing demos, I was doing calls, one for like product discovery, development, and then, you know, it got to a certain point where, like man, I can't be in six, seven, eight demos a day and build the business. So you know, there just comes a point where you need to hand that stuff off and more importantly is, once you can hand it off to the right person, that can sell and generate sales for you, it's the best thing. So sales, I would say, is like that first hire for sure and being able to generate cash which you can reinvest in growth.

Speaker 1:

How did you go about finding your co-founders? Because I've heard horror stories of bad co-founder matches, and then I've also heard the successful sexual stories as well, where you can even imagine having built that business without the other.

Speaker 2:

Yeah, I mean with Call Loop. This was 2011, 2010. So I had an idea and I just found some different APIs that were out there that allowed sort of voice and voice technology. So I reached out to the company, asked them if they had any resources to help get this built. They introduced me to one of the developers and that developer ultimately became my business partner for CallLoop. So he was the developer, he built the product. He was still working full time and ended up buying him out, I want to say in 2015, something like that.

Speaker 2:

But then on the sales message side, you know, I was working with a friend of mine and he was building some other apps and some other sort of things we were playing with and, um, long story short, we ended up like sort of partnering up and then went and built sales message, um, but that didn't work out and so, yeah, I think he was a little bit younger in the sense, and so we just we ended up parting ways and I ended up finding a new co-founder in 2020.

Speaker 2:

So that previous co-founder was with me for you know the beginning stages, but in order for the business to sort of see that next level, it just it needed someone a lot more senior and it was probably the best decision. You know, found a great co-founder he's still with me today, sergey, and we built a great product, a great company, a great tech development team and he's been a big part of that. I couldn't have done that by myself and certainly not with the previous team. So I got introduced to him through a friend of mine who runs sort of a CTO mastermind, and I reached out to him, let him know what was going on and he introduced me to some folks and had a great conversation with Sergey. He helped out with some stuff I had to like offboard the team and we just started working together and through that working relationship he sort of became that new co-founder slash CTO and you know it was 2020. So you know, almost five years ago.

Speaker 1:

So yeah, it really is a leap of faith at first, but if you can sort of walk before run with those partnerships which it sounds like he stepped in and you got to work with him a little bit before you made the full leap.

Speaker 2:

Yeah, I found that to be a good way to test the waters.

Speaker 2:

Yeah, and also, too, it's like um, you know, you want the right partner where you have a good sort of venn diagram overlap, and so, you know, I recently was going to partner up with a friend of mine and we did like, formed a company and did some other things to just build this little app and realized like, wow, we're actually more of the same and so that wouldn't work out.

Speaker 2:

I'm glad we sort of realized that early on and because we were both like similar in the skill sets that we could offer, and so it just got to where I was like, hey, you know what, actually I don't want to do this and I know you don't want to do this, and so we just end up parting ways, still remain friends, but unless there's a true differentiator and skill set, then you know it may not work right, because you're just sort of now competing against the same set of things that you're both going to do. And so, yeah, like there has to be a clear delineation between like, hey, I'm going to handle this part of the house and you're going to handle this part of the house, but if it's two of the same people and they're both doing marketing and both doing messaging it. It doesn't tend to work out as well. At least that's been my experience.

Speaker 1:

I mean you're far. I find it far more effective to be able to divide and conquer, and there's still a little bit of overlap, so you can be in sync with one another and can at least have some sort of working dynamic there. But at least in the case of our new business I had 25 years of experience of being very different than my brother, who's the co-founder in this organization. So it was very obvious who's who was gonna own which parts and who was gonna own the others yeah and that has that has worked out pretty well because of the difference.

Speaker 1:

if we didn't, if we were the same person, then again to your point. It would just be you know competing for the same you know thing, and there would be gaps that would not be filled by it, right?

Speaker 2:

And then you'd have to hire somebody to fill the gap. And so you know early on. It's like who's going to be filling in all the gaps, because you only have so much money, time, resources, and if you can move together then you can close the gap. But if you've got one really strong area, but then there's this other part of the business that just needs to get full, well then who's going to do it? And either you've got to learn it, which may or may not be the skill set you want to learn, or you've got to hire for it and bring in somebody in there.

Speaker 2:

So, you know you've got to have a pretty solid foundation from team to get it sort of bootstrapped up.

Speaker 1:

So, hopping over to the product side and what you've built, and given all the experience that you have in the messaging space, how should business owners be thinking about SMS as it relates to you?

Speaker 2:

know more B2B interests. Yeah, I mean, the way that we look at it is it's it's through a framework called text eyes, and so what that means is, you know, messaging can play a part in the entire cycle. So, whether you're a B2C company or B2B company, like it's all the same, and so text eyes is there's four parts you have capture, connect, convert and care, and so it's all based on this sort of philosophy. But our philosophy is we believe conversations are good for business. The way in which we help businesses create more conversations is through a framework called Text Eyes your Business, and then, ultimately, we have the technology and sales message to like help implement that. So the way to look at that as well.

Speaker 2:

You can use texting to generate leads, right. So somebody can go on the website and do a live chat and you can capture a lead. You can do, you know, text to join. You can have somebody call you and you can automate you know a missed call automation and start a conversation. Somebody can, you know, buy a product, and then they can get SMS reminders. They could fill out a web form, right. There's all the different ways in which you can capture leads, and then SMS is a part of that. And so capture leads right. You can connect, have those two-way conversations. Now, with AI, you can build in these automated conversations so you can use your brand voice. You can engage with them in two way and, again, capture data, push that data to like your CRM. You can use it to drive revenue right.

Speaker 2:

So typical SMS marketing campaign, promotional type stuff. But you can use it to capture reviews right, generate feedback and take these people, turn them into referrals and now they become a referral source. So that's sort of the framework to look at. It is hey, I can textize my business. I can add texting in all the different areas generate leads, book appointments, remind people of the meeting or appointment or schedule, generate revenue, win back customers, get reviews, get referrals right. So that's how we look at it.

Speaker 2:

Most companies that are really coming into it. You know SMS marketing has been sort of the old traditional way like, hey, it's one way texting. But now, as more consumers are not picking up their phone, not responding to email, you know they're leaning on SMS and so businesses need to lean into hey, how are we using texting? You know, when somebody goes to our website and they call us or they text us, is are we actually getting those texts? And so sales message sort of fills that gap. So you can use it for two-way conversational texts, for calling for SMS marketing, right? All those different use cases. So everybody is generating leads and the question is well, what are they doing with those leads? You're either calling them, you're emailing them, and now you're texting them.

Speaker 1:

So you mentioned integrations and I think that's one of the key points. And I think that's one of the key points and I actually I stumbled across your business way back, I believe, in 21, when the agency that I was running was a HubSpot Platinum partner at the time. So I believe we actually use your solution within HubSpot. But I think that integration component is so critical because you're not asking somebody to transition CRMs. Because you're not asking somebody to transition CRMs, you're just plugging into what they already have in place and it's an additive component to what the prospect lifecycle or customer lifecycle could look like. How did you go about identifying HubSpot as an area we should integrate or Pipedrive, as a new platform that we should move into?

Speaker 2:

How did?

Speaker 1:

you go about that.

Speaker 2:

Yeah, I mean I came from like the Infusionsoft world. So you know we used Infusionsoft, so we integrated into Infusionsoft and we integrated into ActiveCampaign and then we integrated into HubSpot and so when I look at, like, what's the customer profile? You know ActiveCampaign is really heavy on the automation side, so it's gonna be more SMS marketing right on the automation side. So it's going to be more SMS marketing right. Keep same thing, small business going to lean on more automation because they don't have a team and people. And when you look at like, okay, well, what's the actual business profile for a business that's going to use two-way texting or yeah, like conversational messaging, and so HubSpot was a good integration. So you know, we integrated I want to say 2019, 2020, something like that when their app marketplace was sort of brand new and it just worked. You know, because, again, those businesses were heavy on inbound marketing, right, they're heavy on conversations and so messaging and texting just played a good part of that.

Speaker 2:

And you know we've gone deep on the HubSpot ecosystem. So if you use HubSpot, by all means, like, check out sales message, and so they have, you know, sales hub, marketing, hub, service hub, operations, hub. So we integrate super deep in all those different hubs. So your sales team can use it, your marketing team can use it. You integrate into workflows, your customer support team can use it, your marketing team can use it. You integrate into workflows, your customer support team can use it with tickets, so all across the whole company, you can essentially integrate messaging right, you can textize your business.

Speaker 2:

So HubSpot, you know, just the signals were there and so that's why we just continued to double down and go deeper and deeper and deeper on the integration. Hubspot always exposes new access, new APIs like new ways in which that we can extend our integration even more. And so, yeah, I mean that's that's why HubSpot is, because that's really where the customer was. We do integrate into other tools, like we've got a pretty good Salesforce one. That's a different beast in itself. That's more enterprise right, sales cycles, totally different. Um, but HubSpot for us is sort of our main, our main integration.

Speaker 1:

We use the sales service and marketing hub, so I'm going to have to go check it out after this, uh, after this podcast, see if we can leverage it. Um, as it relates to like, uh, you know, leverage it. Yeah, as it relates to, like you know, opt in and managing that entire process, is that something that that you take on, or is that beholden on the, on the customer?

Speaker 2:

Yeah, I mean, we've got a pretty simple system to go through that process. But you know the carriers. Years ago you could send texts to anybody, upload a list and texts and, you know, get your message through. You know, behind a short code or just provision a phone number, carrie's got pretty smart and they're like, look, if we're going to keep this channel clean, we've got to set up some, you know, some structure so we can keep it clean. So they really want to know two things like who you are and what you're sending. Right, so this whole know your customer KYC. So, hey, I know your business, you're a real business. And hey, what's the type of messages you're sending? Maybe it's marketing, maybe it's customer care, whatever. So they can walk through that process.

Speaker 2:

So if you're going to get a local number or something called 10 DLC just stands for like 10 digit long code but you go through an approval process through sales message we submitted to the carrier. We actually got some good AI stuff, because most people are like, oh, let me just submit it and submit whatever data over to the carrier, but they don't realize like it's not us, it's actually the carriers that are going to review it and the carriers are the ones that will say, yes, this is compliance and we approve it, or no, and so people can't just assume they can put in whatever they want and then it gets approved right, because if you don't get approved, you can't send texts. So we built some pretty cool AI tech to review it, take a look at it and ultimately help our customers make the right decisions around getting approved right, because they got to update some stuff in their web form and whatnot. But they can walk through it. It's pretty simple.

Speaker 2:

It's just a form Tell us information about your business where people filling out you know form to capture an email and you know you submit that stuff. We send it off to the carriers. Either it comes back approved, it comes back rejected with some suggestions and they just go through that process process, but it's fairly quick within a couple days. You know they can get approved and then send text. But everybody has to do it. It's not like a individual thing, it's every company yeah, that makes sense.

Speaker 1:

One last question for you, as it relates to your favorite use cases of sales message. Is there a way that you use it internally for your own business that you think you know every other company should be leveraging it for that way as well?

Speaker 2:

Yeah, like you know, I was helping a friend auditing his business because there's so many opportunities that people don't realize. So I think one of the hidden ones is most people, I would say most. You know older businesses, maybe they're using a landline and so that landline traditionally is only calling, it's not texting. So what they can do is we can text enable that number, and so that number becomes textable and they realize, oh my gosh, there's people actually that are trying to text me. So that's just like a hidden gem of leads and opportunities that people are trying to message you.

Speaker 2:

The other, like I think you know, a lot of these strategies are not revolutionary and so that's why, like SMS, you don't see a lot of courses on it, because it's like you're just sending a text message. You don't have to learn copywriting. There is some strategy around all of that copywriting, right, like there is some strategy around all of that. But you know one super simple one like this is obviously most DTC type stuff, but you know one of the ones like we've, we have a lot of speakers and so they're in front of an audience. So a buddy of mine, this is a very old strategy but it still works. So he was speaking in front of 150 people a simple text to join keyword and I'm generating over 100 leads. So, text to join or scan a QR code, go into an SMS sort of AI agent. That AI agent is capturing your name, your email, square footage like whatever custom data, and he generated all those leads and then put those leads in HubSpot and started a whole automation sequence. So you know, the future is really well. How can you turn all these mechanisms into lead gen, putting them into, you know, an AI agent to have those conversations, to capture that data or qualify to book a meeting or drive revenue?

Speaker 2:

And so, you know, I think the traditional exit pop, you know, capture a cell phone and then send. You know, marketing promotion is great. I mean, it works crazy specifically for, like e-commerce. But I think, as you sort of get outside of that, how do you really add messaging in a way that can help you grow more effectively? And so that's our goal. You know we've got a pretty awesome platform integrate super deep into different tools and systems. And yeah, I mean just doing a simple audit on the business. Hey, do I have a web form? Am I capturing a phone number? What am I doing with that asset, because it's an asset, right the same as if you're capturing an email. You've got your email asset. Now you sort of have your phone asset and that can be through calling but also be through SMS text messaging.

Speaker 1:

I love some of the best use cases and applications are the most obvious but also most overlooked, I feel like. So yeah, that makes a lot of sense.

Speaker 2:

It's usually the case, yeah.

Speaker 1:

Well, I appreciate you coming on and sharing all these insights.

Speaker 2:

But before we hop, can you let people know where they could you know about you? Or sales message. And yeah, thanks, brandon, I appreciate it. Um, they can go to sales messagecom. Take a look at our platform, sign up for a free trial um test it out. And again, we integrate really well into a lot of different tools and systems. Um, but they can try it out, get a phone number, play around with it and and hack at it.

Speaker 1:

But salesmessagecom. I appreciate you coming on. We'll edit it. We'll mute that For everybody listening. I appreciate you coming on, chris. Thanks everyone for listening. As always, you can find me at brandonorosocom or Scalistai. Thanks for listening and we'll see you next time.

Speaker 2:

Awesome.