Steve Benson 00:02
So, from a customer success perspective, I believe that people under-invest in the success of their customers, and that raises churn rates, lowers lifetime value, and it’s a very clean investment.
Intro 00:20
Welcome to Across the Funnel, where we dig into concrete Go-To-Market moves across sales, customer success, and account management, so you can build revenue that lasts.
Brought to you by Hyperengage and Dextego.
Adil Saleh 00:34
Hey, greetings, everybody.
This is Adil from Hyperengage podcast, and I know that this has been turning and spinning different topics from the recent quarter or two that we are trying to make sure we dig in different unique topics and unique challenges brought by AI.
Although a lot of these topics are purely built on thinking how AI can make a positive impact, there’s a negative side of things as well, and that’s what we’re going to be talking about. That is field operations, field sales, field services, how big of a shift that we are going through at this moment from mid-to-enterprise segment in tech and overall in general as well, oil and gas, manufacturing, real estate, that has always been there, but real estate also tried to be kind of like tech, selling the times, but again, there’s a big component of sales organization that are on the field, the service, and how they’re being impacted by technology.
This is what we’re going to be talking about and how critical it is for them to have technology enablement in the time of AI.
So today, we’re going to be talking about Badger Maps. We have today with the founder of Badger Maps, Steve Benson, with us, who was previously a sales leader for many years, close to two decades, serving in Google, leading sales team.
At one time, he was awarded and recognized for one of the top performing sellers back in 2009 by Google.
So thank you very much, Steve, for taking the time today and helping us learn more about you and your journey at Badger Maps.
Steve Benson 02:18
Absolutely. I’m happy to be here.
Adil Saleh 02:19
Love that.
So, Steve, let’s first start. I know that you’ve been, you have a tech background. A lot of these field sales operations, they don’t understand and see tech in the way that it is now in the year 2025.
They still think that, hey, we’re still living in Salesforce and all these legacy tooling and everything.
But how did you transition into building a tech company from the very beginning? I know at core, at fundamental, you’ve been a sales guy, getting in the trenches, talking to people, having coffee table talks and in-person meetups.
But how did it all come along when you started thinking about building a technology that is going to enable these field operations, service operations with routing and territory and all that Badger Maps?
So could you walk us through all of that?
Steve Benson 03:00
Yeah, for sure.
So my background after business school, I went into technology. I worked at IBM selling software and services and hardware, which is a really fun general background on the tech industry.
And then from there, I went to another software company and focused just on software. One of the first software companies that had a cloud product, a company called Autonomy that ultimately got bought by HP.
And then from there, I took that knowledge in the cloud, because we had just transitioned to that company from selling CDs on disks to selling it in the cloud.
And I took that knowledge and went to Google, selling Google’s enterprise software products for a few years. And the last product I was focused on was the Google Maps API.
So I had a background in sales. I was working with the Google Maps API and where to apply that technology in the world. And that’s how I came up with the idea for Badger Maps.
So it wasn’t really a super creative play since I had the sales background, mapping background to create a mapping tool for field salespeople. I don’t get any awards for most creative, but that’s how it came about.
And so I left Google in 2012, beginning of 2012, and started up Badger Maps.
And we set out to solve the problems that our field salespeople have that are primarily mobile based and map based.
So, you imagine the difference when an inside salesperson and a field salesperson, the field salesperson is moving around and they’re out in the field. And so they’re very, very mobile.
They’re one of the most mobile types of employees, and they need to be connected to all their customer data, which lives in the CRM system.
So that was the problem that we set out to do, was connect the data in their CRM system to a map. And that’s what we’ve done.
And now, here it is 13, is it almost 14 years later? Here we are. Badger Maps is about a hundred person company now. And we have five products that serve field salespeople.
Adil Saleh 05:26
Interesting.
And the key part is to be able to bootstrap this platform as a founder from the commercial side of things is kind of a big validation of this problem being big enough.
And then you being a salesman yourself, you’ve lived all this life, working at IBM and Google and all this.
So how did all of this become when you actually build the product and the Go-To-Market side of things, how big of a challenge that was?
I know you had corporate footprints already working with people. How did that go in the beginning?
How did the team come up, the co-founders, the entire, I would say that startup is always a place of problems, right? So there’s a handful of people to get to see that bought into those times.
So how did that journey go along?
Steve Benson 06:22
Well, yeah, I mean, I think the key takeaway there, and there’s always challenges, as you refer to, the key takeaway to bootstrapping, otherwise known as not raising outside funding, is someone has to be rich or they have to have money already to pay for things like engineers, marketing teams, salespeople, all the things that you need as you build a company.
Someone has to be able to pay for that.
Or a basic version of the product needs to be sellable to the end user that is willing to pay for a basic version of the product.
Not everything is bootstrappable. Not everything can be bootstrapped because it’s too technically complicated to build a basic version.
For us, fortunately, you can build a basic version of what we built in the browser. You can use the Google Maps API to put points on a map. You can build a basic version, spreadsheet upload relatively quickly, right?
And what’s harder, there are harder things that come up later, obviously.
But the initial thing, we were able to give enough value to customers that they were willing to pay us. And that was really the key to bootstrapping.
So if you can go to market relatively quickly and generate revenue, then you can take that revenue and invest it back into the product.
And that’s the real key for bootstrapping.
And you just can’t do that if you’re building quantum computers, right? There’s just too much money and too much needs up front that you can’t sell a basic version of it. It’s too big of a hurdle.
Whereas for us, it was a series of little hurdles. It’s like, well, this group of customers, we need this the very most. We can give them a basic version and they’ll pay us money, not as much money as they would pay for the full version, but they’ll pay some money for this basic version.
And we’re able to do that and give people more and more value over time. And that was really the key to bootstrapping.
Adil Saleh 08:43
Yeah, absolutely. 100% agreement on this because at the end of the day, whatever cost that you have, you got to make sure that the quickest you can deliver value as bootstrap founder, easier for you to pay for the recurring costs of the technology and team.
Even if you are spending all your time with a handful of people, you got to make sure that you make enough revenue as a product or able to validate it with the people or companies that actually are willing to pay.
Instead of a lot of these startups, I know that your product is slightly different, but a lot of these startups that go with freemium plans and they try to get some traction in the beginning, but the cost has to be pretty low with AI, APIs and everything today.
The cost is so hard to do the economics right when you’re not generating revenue or pre-revenue. Interesting.
So now we’re going to be talking about AI a lot later in the segment, but I’m more interested in first talking about what’s your viewpoint as a sales leader and the core B2B SaaS, I would say mid-market to enterprise investing into field sales.
I know that they are still investing, but they don’t have fully organized, like you have VPs of sales, they have VPs of revenue, but they don’t have specifically leadership or a category of leadership or divided a suite division of operations only for field operations.
Some of the companies that came on are probably like MuleSoft and all these companies that are doing sales versus Slack.
They have their teams, but what’s your viewpoint of trickling it down, making sure that they have small, mid-size companies that do have people on the field side?
How do you see this category moving? What’s your view on this?
Steve Benson 10:32
Well, for starters, our main market isn’t technology.
So technology used to be sold with field salespeople. That’s how I started my job out. It was meeting people face-to-face.
As software has gotten cheaper, we’ve ended up spending just as much money on software because it’s thought of as a monthly expense. It’s not as big on a monthly basis, or even an annual basis.
Whereas I used to sell a CD for a million bucks, right, way back in the day.
But as this has developed over time, people have been willing to invest less in the relationship and you don’t fly out to meet with your customer in Kansas. You just meet with them over a Zoom.
Whereas in 2007, I would have flown out to meet with them because it was going to be a big upfront spend. There’s risk. They’re just getting a CD, right? They want to make sure they’ve got to trust you. They’ve got to know it’s going to work.
It’s a lot easier to be like, oh, well, you can just try it out. And that takes a lot of the risk away.
And I’m not paying a million bucks. I’m paying 30 grand a month.
So the software industry has moved away from field sales and towards inside sales.
But that’s not our core market. Our core market is things like med device, pharmaceutical, construction, health care services, stuff like that. Things that the main way they go to market is meeting people face to face.
I actually believe that for people that are selling expensive pieces of software, and if it costs more than 50 grand a year, it’s expensive. That’s a meaningful investment.
People need to trust you that it’s going to work. They’re putting real money behind it.
I imagine in those cases, and certainly this is how we behave, if you meet someone face to face, it compresses the sales cycle, lowers the risk for them, gives you a competitive edge over your competitors, et cetera.
I think people don’t do that enough. Basically, people don’t do field sales enough in technology compared to, in a lot of industries we talk to, if someone’s going to be spending three grand a month with you, of course you would send out a field salesperson. That’s a big deal, right?
Whereas in software, we’re like, oh, maybe if they were spending 10 grand a month, we’d fly out and buy them some steak. But otherwise, no way.
So I do think that there’s a missed opportunity there for software companies to do more field sales and to meet with their customers more often, both before and after the sale.
I would say meeting with customers after the sale, whether it’s an executive or a customer success associate, someone who’s in charge of the relationship post-sale, I think that lowers churn, builds trust and enhances communication, gets customer case studies, that face-to-face interaction is valuable there too.
Adil Saleh 14:00
Love it.
And because the biggest problem is, again, of course, average that mid-market to early enterprise, these small enterprises, they always have their average contract value of more than 80 to 150 grand. It’s just that.
And a lot of these are spending time in building and forging relationships with their customers because that’s a big opportunity to meet in person. There’s no substitute of in-person meeting, any substitute.
So, and by building relationships with the customers that enable them to rekindle, increase the lifetime value of the customer.
And that is the biggest challenge, to be very honest. The net revenue retention in the tech today, even smaller companies going upmarket because they have just moved on to meeting those and all these online meetings and weekly cadences or quarterly business reviews online.
And they get a lot of data from a million different sources. And they already know about their customers, their interaction and everything. And this is what we do at Hyperengage, by the way. I’m a big believer in that too.
But there is a huge opportunity that they are missing out by not deploying their team members for a specific contract value that makes sense economically, to go in person and have those kind of trust level and relationship level, even as you mentioned, pre-sales and post-sales, and helping them see value and know you more as humans, as teams, as culture.
And you get to know them more too.
And that’s why all these big companies, you talk about Fortinet, you talk about Google, you talk about MuleSoft, Salesforce, all these big companies, they have, of course, they don’t have an organization pretty much built on just for field sales, but they have a lot of their tech team people, pre-sales, post-sales going, meeting their customers and having coffee table talk, going to clubs together.
I think we’ve got some really cool stories from the team at Fortinet that they do with their clients, for different hangouts that they do just to build the relationship and all of that.
So relationship piece is also, as you also mentioned, has been missing in tech.
So now you mentioned that you’re more in the manufacturing, and what is customer segment? Are you trying to go up market and penetrate?
Steve Benson 16:18
So the biggest industries for us are people that sell expensive things, competitive things, recurring revenue things, often related businesses where relationships are important.
That tends to be where you’ll deploy a field sales team out to talk to your customers. Commonly found in things like medical device, pharmaceutical, construction, healthcare, things of that nature.
The different things that we do for people, our flagship product is called the Badger Map. And that’s basically a map on your phone and it’s linked up to data that’s in your CRM.
Usually, you can also upload a spreadsheet, but it’s your customer information and we give it to the field sales reps in a mapping and routing environment.
That way they can build out their schedule for next Thursday when they know they’re going out to this suburb to visit this customer, they can see who’s on the way, who’s on the way back.
What if I went this way? Who’s important? Who do I want to see? Who haven’t I seen for a long time?
All that data that’s in the CRM, we make useful for making decisions about who you’re going to be spending time with when you’re in the field.
So that’s kind of the first and the primary thing that the company does. That’s our flagship product and what we started out to do.
After that, after we built that, we built a territory design tool. So a territory alignment tool, meaning I have 150 sales reps across the country. I would like each one to have a fair territory, a balanced territory.
And to me, I’m balancing the territories on fields in the CRM, but the fields for me are things like how much revenue is coming out of that customer, how many customers are there in this territory, how many prospects are there in this territory.
Build me territories that are fair, 150 of them across the country that are fair based on those particular metrics. That’s different for every customer.
And then we’ll automatically generate those 150 things and give them a bunch of tools to tweak them and change them as the sales team changes.
It’s like, oh, well, we just fired the person in the Seattle office who is in charge of that territory. And we know someone who we want to hire is in this Kansas office.
So we want to shift all the territories a little bit to the left, right? 2% to the left and things like that.
And people are constantly like, oh, this person went on paternity leave. So we need to shift their territory down for the next four months and have everyone pick it up evenly.
We can’t just give it all to this person because that’s not going to work.
So it’s a constant adjustment to all the territories. And we built a piece of software to do that.
And then we’ve got a handful of other tools like lead routing. Like as the leads come in, we automatically route them to the proper territory, and a handful of other mapping and other useful tools for field sales teams.
Adil Saleh 19:24
Absolutely. One quick question on this.
And before we jump into it, do you guys also have reporting dashboard for, like, let’s say if I’m a head of operations, sales operations, like field operations.
So I have like 150 field reps going all across the East Coast. I’m able to see like, hey, these are the activities.
These are maybe some of the, some of the accomplished key takeaways that I need to get on top of for all these reps and all these critical meetups.
Steve Benson 19:51
Exactly. Yeah.
So first we have reporting on all the data coming out of the field.
And a big part of the value of the product is Badger Maps is effectively a front end to the CRM with a mapping and routing environment. So you capture data in it.
If you’re capturing data into the CRM, often they’re built to be best used on computers.
So you’re often at, but someone who’s on the run, it’s like, they’re leaving this meeting and they’ve got another meeting in 20 minutes and they’re not going to swing by a Starbucks and log into the internet and get on and hunt and peck around the CRM to take notes.
They want to just do it really quickly on their phone.
And most, if not all CRMs at this point have mobile apps, but what’s useful about our way of capturing data is it’s right in your existing workflow.
So like at the end, after you visit someone and you’re about to go to your next meeting, we’re prompting you, hey, fill out these eight fields that your company really wanted filled out about every meeting.
And then those fields go to the different areas of the CRM where they’re needed.
So it might be under, this field might go to an account tab. This field might go to the opportunity object. This field might go to the contact object. And this field is like a task object.
And so that we’re filling out the right things in the right places automatically without the rep having to do it.
And giving them the ability to use things like dropdowns and speech to text is really useful to capturing that data really quickly. And that’s a big part of the value.
But then you can run reports on all that to your question.
Like we have reporting and all that stuff that’s happening. Whether or not you’re using it with a CRM or standalone, you have that.
And then also we have a dashboarding and gamification product called Scoreboard, Badger Scoreboard, where you can see charts and graphs.
There’s a piece for leaders, but there’s also the individual reps. You can give them a view of how their performance is in charts and graphs compared to their peers.
And there’s a gamification element. Field salespeople are competitive individuals. A lot of times they come from backgrounds like athletics. They played football in high school and they’re competitive.
So it’s good to show them how they’re doing against their competitors, the other sales reps.
So their team members, but their other salespeople are competing with one another from a performance perspective.
And so it’s nice to show them, well, hey, this is how many meetings everyone’s done so far this month, like face-to-face customer meetings that have been done this month, capturing all that data and showing it to them in a bar chart.
And they can see where they are relative to everyone else.
And you can choose whatever you want to show them. So you’d be like, okay, here’s meetings and here’s sales.
And they’ll be able to see, oh, the people who are doing the most meetings are also getting the most sales.
So, or whatever the real needle movers are for your business, you can show them charts and graphs on that, that are particular to their territory.
Adil Saleh 23:04
Love it.
And this is more relatable to other reps as well.
Let’s say, for example, five reps working in New York City and they already know what other reps are doing there.
What are the quick wins that they have and all the data and everything, and they feel motivated, and they cannot relate to somebody like in Kansas City, as you mentioned, so territory brings them closer to how they echo with those operations and on a level of different accomplishments they want to get out of it.
Perfect.
So now I’m thinking about, you’ve built a lot of things in the product, in 12 years.
I know that you’ve been a part of the Google Maps team as well, back in the years, like you worked on the API as well.
So now that you have integration with Google Maps, that would be this territory thing.
Now this reporting and scorecard that you have, how did you see the AI when this first time had a GPT-3, as a chief executive, what are you thinking?
Like how fast we can do, what kind of initiatives you did take at that time with this generative AI and everything, and what’s your viewpoint of its impact in your industry, like building apps, bringing technologies for teams in the field?
Steve Benson 24:18
Yeah.
So I guess when I first came into contact with the technology, I wondered what it could do for us. And I simply started experimenting and exploring it.
I think it does different things for different parts of the organization and speeds up different processes in different ways.
I guess to your question, like, what did I think from it, in terms of capacity to build more tools faster, I think that’s certainly an area we’ve seen it really speed up.
And the engineering team is one of the teams that’s gotten the biggest lift.
I’d say engineering and probably also marketing have gotten the biggest lift from AI.
It’s able to do a lot of the things like research, where taking a long time to figure out how something worked or how to understand it.
And now we’re able to get those answers really quickly.
It’s able to write code. It’s able to do a bunch of things that make the engineers go faster.
And that’s going to have a lot of really interesting impacts.
I think it’s one of these technologies that’s going to touch every organization and make us all faster and more efficient to some degree.
Adil Saleh 25:31
Yeah, that’s about it.
Since you’re building apps and you’re capturing data, with this AI, it’s all about data.
So as much as you can ingest it and give it a context, it improves the capabilities. It’s that simple. And you can do it at scale.
We’re learning more patterns about different customer verticals, industry verticals, customers and field operations.
And I know that there’s such a diverse kind of field operations that are getting to use Badger Maps.
And you always learn. So previously it was humans, now it’s AI.
So AI is always going to be faster at replicating, faster at understanding the contextual component of it. And that’s how you actually train it.
So are you also thinking about training or fine tuning the AI models for apps and territory that you mentioned, make it really smarter on a base level for some layman like me, like I’m using Google Maps and let’s say the streets of San Francisco versus I’m using Apple Maps.
I see Apple Maps is more intelligent in terms of some of the data layers that they have on top of these mapping APIs and it gives you different outcomes.
So how you are investing or thinking about investing, making this navigation or this routing more and more efficient, given the data and capabilities of the app?
Steve Benson 26:54
Yeah, well, I mean, in addition to making us just be able to build more features faster, like with traditional engineering, it just speeds up traditional engineering.
We also can incorporate it into our product.
And so that’s something that we’ve done is we will make suggestions to salespeople about which customers we believe they should focus on, given where they’re already going to be near on the map.
So if we know someone’s building a route and they’re going to be driving an hour this way to go see this dentist in Springfield, they can hit a button and say, hey, Badger, would you suggest to us who else I should be focused on in that area?
And we’ll, by looking at their data, give them five recommendations of, hey, these customers look like they should be seen for these reasons.
And then if they want more, they can just hit a button again and get five more.
And usually it’s like salespeople have a lot of context and it just isn’t in the data a lot of the times.
So that’s why we designed that that way.
It’s because they’ll look at the five and they’ll be like, oh, that one and that one, wait, let me see this one, and look at all the details of like, oh no, not that one because of this, but then they’ll ask for more and then we’ll give them more.
Right.
So they have context and knowledge that we don’t have, which is why we just suggest it.
And then they can just click on the ones that they want.
And then they add that to their route and then we’ll optimize the route and do the best way to go through all those points, obviously, and build the schedule and do all the other things we do.
But we’ve incorporated AI and machine learning right into that workflow.
Adil Saleh 28:49
I love the way that you’re taking an augmented approach with human in the loop, because of course, a lot of things are mission critical.
And of course, recommendation can be close to being efficient, but couldn’t be efficient without a human in the loop. They have to prove it.
Because that’s what the job of AI is. It’s not to replace a human, to augment a human capabilities.
Let’s say you might’ve come across previously used to have like 10 or 15 people on the team to do some certain thing in technology or machine learning.
As you mentioned, data science. Now you can do it with 30% of the people. It’s been cut like 70%, even more. A lot of these companies are claiming more, but to be realistic, it’s 70% cut down.
Perfect. So now we have around 12 minutes, and I’m absolutely loving this conversation where it’s going.
Now, this event that we did, I talked to you about October 28th, exactly one month ago. We brought CS leaders, Go-To-Market leaders, founders from the Valley, some came from New York City too, and we talked about, hey, that’s fine. You’re growing year on year, investing into acquisition, doing the marketing, customer education, training and all that. How much of that are you putting back into the success of the customer?
So how you’re enabling them in terms of training, in terms of recording their interactions with the platform, and channeling them to the best success metrics and best value paths. That was the name of the event, like deriving Value Path in the Go-To-Market 2025 or 2026.
So we had a CCO of Vercel. I’m sure you know these folks. Paul, great guy. CCO of ContentSquare. Both of them are pretty big, close to 10 billion valuations.
So now what is your viewpoint, and what kind of initiatives are you taking internally towards success? It could be as simple as, hey, we know that these are wins in certain territory. We already know that these are success parameters in terms of data points or interactions inside the Badger Maps app, inside of the Territory app, inside of the gamify apps.
So how you’re interacting those usage metrics and articulating it for their success and putting them right. They’re not on it. Like, let’s say they’re not fully onboarded, they’re not well adopted to the platform, activated to the platform. They’re not consuming it in the right way. They might be underusing some of the features.
Maybe there’s some strong growth opportunities that you’re not on top of. So maybe we can talk about in the renewal. So the goal of success is helping them see value fast, helping them retain, helping them expand and increasing the lifetime value as partners, as family members, to have shared values, not like forced retention or forced expansion.
So as a CEO, what kind of initiatives are you thinking? We are doing that, by the way, at Hyperengage, enabling these teams, but this is a big, big talk.
Steve Benson 32:06
Yeah, absolutely.
So, from a customer success perspective, I believe that people under-invest in the success of their customers, and that raises churn rates, lowers lifetime value, and it’s a very clean investment. Usually, if you have a nice product, it’s still probably too hard for people to use without help, right? And without someone to pick up the phone when they have a question.
And so I think one of the first employees you should have, right around the time that if you have enough money to hire a salesperson to win business, as soon as they start winning business, you should have enough money to hire a CSM, someone to run your customer success and make sure that customer is onboarded successfully.
If there’s integrations involved, integrates successfully. And it’s going to drive renewals. That person’s in charge of the renewals, and that frees up your salesperson and they don’t have to deal with any of those things.
So I think it’s a great strategy to have people that are dealing with the customer until the sale occurs, and then someone who deploys and manages that relationship going forward, including the renewal and any upsells.
And so I think that’s somewhere that people under-invest. I think customer support is another area people under-invest. And that’s the quick interactions people need to have with you regarding your product, right? It could be they just need something tweaked or they need something changed. But having a customer support team that it hits their desk, they just take care of things quickly and efficiently with tickets. And if they need to escalate it to the customer success team from customer support, they have that option.
In terms of trends for this job type, I think using data better is a big trend for this type of group. Like figuring out what are customers doing with the software, what is this particular customer not doing with the software, not taking advantage of, and finding out why, or enabling them to do better, is really important.
I think partnerships, so making friends with the other people that are involved in the ecosystem. So if we work with the CRM, our people that manage Badger and help our customers should be in touch with the people that help them manage their CRM. So their strategic integrator partner. They go by SIs, the partners that deploy the CRM, help manage the CRM for our customer.
It’s more common in some CRM ecosystems than others, but if you buy Salesforce or Microsoft Dynamics, it’s enterprise CRM for larger companies in general, you’ll almost always have someone externally that helps deploy it, manage it, et cetera.
So we need to work with those people because we touch that piece of software and to the customer, it’s all one solution. And so partnerships, I think are also very important and under-invested in when people talk about their customer success.
Adil Saleh 35:34
Love it. And I know that this is the core function of success, like in the KPIs and goal, what they should be responsible for. You mentioned renewals and mitigating the churn and all.
So how is that in place at Badger Maps? We have a handful of minutes. What kind of initiatives are you taking in terms of using Google Sheets or updating, having some sort of workflow automation currently for your success, or customer support?
Steve Benson 36:06
Yeah, I mean, because they’re customers, we try to keep all that data about our customers in the CRM system.
I think you want one place where all that truth exists.
Adil Saleh 36:19
System of record. Yeah. Source of truth. Yeah. And one system of record. Yeah.
Steve Benson 36:32
Now does that mean we never use spreadsheets to keep track of this project or this task, or this? Of course we do.
But we try to keep that type of data in the CRM.
There are add-ons to some CRM systems that are specifically for the customer success rep and that management of the customer, and they’re often also connected to the data coming out of your product, showing who’s using what and when, and how.
We don’t use one of those, but I’m told they’re very useful. But that’s not something that we haven’t gone to that level, so I can’t tell you, oh, this customer used this exact feature and pressed this button at this time. So we’re not that granular with it.
But we’re still a smaller company. I think as you get larger and larger, you tend to focus more and more on those details.
Adil Saleh 37:22
Absolutely because you can set some sort of like high level success metrics on maybe journey level, like whether they’re fully onboarded, whether they’re activated, whether they talk to our support and being served, these kind of parameters. Yeah.
And you can still do within your CRM regardless, that sort of thing. I would
Steve Benson 37:40
Absolutely recommend doing within the CRM. Yeah.
Adil Saleh 37:43
Yeah, absolutely. Because a lot of these customers and even our partners and fans that are doing business at tech and these kind of verticals, they’re also starting out with this.
And then you evolve, as you mentioned, as a one system record, to get your team equipped and you see with these basic parameters around success. Around support as well, because support drives success is an analog of sale. Success, just like marketing is an analog of sales. Who knows it better than you, by the way?
So this is quite interesting that you’re thinking around those.
So now last question to you is, I was kind of curious too in picking your brains on this. Like how do you see being a bootstrap business? I’m also a bootstrap business, but I’m creating, seeing a lot of noise.
A lot of these founders come to my podcast and LinkedIn gives me depression. Some sort like, hey, I’m not raising a seed round with a really good accelerator, VC.
I look up to these folks, Jason and David, founders of Basecamp. They’re also the creators of Ruby on Rails. And they’re one of the finest bootstrap companies. And they’re going to be one of the few to be a 10 billion valuation company in a few years. Wish them best.
But how do you see it? Does it give you a freedom versus does it give you, hey, like I gotta go slow in my own pace, have the freedom and all that mindset, or second, hey, I know what I’m gonna do. These are the things that I can achieve and I have enough capital in me and I don’t need investors.
Even not just for the capital. A lot of these investors are strategic. It helps you go into different markets, different regions, different continents you mentioned globally. So what is that that is driving? What kind of mindset that is driving you and what makes you excited in the end of year 2026?
Steve Benson 39:32
Well, I guess the first question is, when you’re asking yourself, should I bootstrap or not bootstrap, the first question is, am I investible? And the vast majority of SaaS businesses are not VC investible businesses.
So there are very specific characteristics that a company needs if they want to be VC investible. Very explosive growth coming out of the gates. Really pretty meaningful TAM and explosive growth.
Meaning, you used to be able to, if you had a million bucks in ARR and you were growing at 40% a year, you were a VC investible business. The bar is much higher now.
I think especially in the AI area, these are very risky businesses, but some will have massive outcomes. AI is a tool, a technology that’s going to be used by every business effectively in the world. And there are going to be AI solutions that collect money from lots and lots of businesses in the world as a result.
So you’re talking about creating new massive technology companies, which tend to be super valuable businesses, so I think there will be some real winners there.
I think that this is a type of technology that, because we’re investing in it, there’s a lot of spillover value, so it’s good for society that we created this stuff in a lot of ways. It’ll be beneficial in many ways. There are some risks with the technology as well, of course. And I’m certainly not an expert in those.
But I do think that that’s the first thing that you have to ask yourself. Am I investible? Given that the bar is set by the AI businesses right now.
So VCs are looking and evaluating, of these 2000 companies that we’re looking at, three of them are going to be huge. The rest are going to be dead. So it’s a real winner, you know. Maybe that’s a little extreme. Maybe not all, they won’t all be dead, but there’ll be, there’s going to be a lot of blood on the field.
Whereas in SaaS businesses, for example, it was like, hey, I’m making a million dollars a year. I’ve identified this group of people who we create a lot of value for. And we will continue to create value for them. The bar was just lower and the revenue was upfront. There wasn’t a ton of cost upfront. So it is a different world today than it was when I made these decisions, for example, I guess is my point.
When does bootstrapping, bootstrapping doesn’t always work. Because it doesn’t always work if you’re in a competitive space where other people are raising money, because it is absolutely a space that is worthy of investment.
It’s hard to not raise money, right? So you have to be in a space that isn’t, that no one thinks is going to have massive outcomes, because if people think there are going to be massive outcomes in it and those competitors are going to attract VC money, then it makes it difficult to compete with them. Absolutely.
Now there’s always a trade off on growth too. Bootstrapping, does it affect growth? It just makes everything take longer, right?
If in 2012 I raised $10 million because my idea was so sexy then, it really took me until mid 2017 to have a great product. I mean, we were selling it and it was on the street in 2013, 2014, 2015, but it wasn’t great until 2017.
And if I had had $10 million to spend, I could have made it great a lot faster. So there’s definitely a time trade off.
I think it does give you a certain amount of independence, which is valuable if you don’t have investors.
But you also lose something too by not having investors, because these are useful people to have around and have on your side.
So yeah, it does affect growth is the bottom line, if you spend less money. But you do end up with greater ownership and greater control at the end.
I think a lot of people act like this is a choice. A lot more people think about this as a choice than it really is. Because you either are in a situation where you basically have to raise VC because it’s competitive and other people are. Or you’re in a situation where VC does not want to invest.
So I would worry less about should I, would I, and I would ask more, could I?
Adil Saleh 44:45
I love the way that you put it. Great, Steve.
It was really nice getting to know you and your journey and all that you’re building and just you’re taking life as it is.
Like, I went to this K2, second highest mountain in the world, last year, and first time realizing in my life, that life is generally and naturally slow. And we made it so fast, artificially.
And we are so tiny, sitting in front of these glaciers and all these mountains and all these streams. We’re just tiny. So that was the biggest lesson that I learned from that K2 trip.
We tracked around 160 miles on foot in seven days. I lost a lot of my pounds, which is good. But that was a memorable experience.
So thank you very much for sharing and being your real self and authentic and concrete in this conversation.
Steve Benson 45:39
Yeah, absolutely. Well, thanks for having me. This has been fantastic to chat.
Adil Saleh 45:43
Love it. Likewise.
Outro 45:44
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