From 80 Doctors to 1,000 Customers in Vertical SaaS

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host, Omer Khan and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
In this episode, I talk to Zach Holdsworthy, the co founder and CEO of Hint Health, a membership management, billing and payment software for primary care, urgent care and specialty practices.
In 2014, Zach and his co founder Graham set out to transform the US Healthcare system.
They were both frustrated with the cost of health care and believed they could make a difference.
They decided to build software to help direct primary care practices.
Despite both of them lacking experience in healthcare, they jumped right in and hit the ground running.
Within 30 days, they had attended an industry event, talked to potential customers, started building a product and got their first paying customer.
And a few months later, they closed their first 10 paying customers.
Today, Hint Health has around a thousand customers, is close to hitting eight figures in annual recurring revenue, and has raised $64 million in funding.
But looking back now, Zach says that if he could go back, he.
He would spend more time researching customers and their problems instead of moving as fast as they did.
We talk about the lessons he's learned over the last eight years and how he'd do things differently.
We also talk about how they overcame challenges and objections their prospective customers had about relying on a startup to manage billing and payments for their healthcare practices.
It's a great conversation and I hope you enjoy it.
Zach, welcome to the show.

Zak Holdsworth (01:49.600)
Thanks for having me.

Omer (01:50.640)
Do you have a quote, something that inspires or motivates you that you can share with us?

Zak Holdsworth (01:54.320)
Yeah, I'd say one of my favorite quotes is luck is.
I think it's Seneca.
Luck is what happens when preparation meets opportunity.
And I believe that to be quite true.
I think in life, a lot of people's success comes down to luck, but the important thing is you've got to realize that and pounce.
Right?
You got to be prepared and like, take advantage of it when it happens.

Omer (02:17.840)
Tell us about Hint Health.
What does the product do, who's it for, and what's the main problem you're helping to solve?

Zak Holdsworth (02:24.280)
Yeah, so we serve a mirror healthcare company.
We serve a community of doctors that are basically stepping outside the insurance fee for service infrastructure in the US Healthcare system and going direct to either patients directly or actually direct contacting with employers.
So we can talk about why we do that.
But the high level is this how we think we can transform the healthcare system and make it better?
And what we do for these customers, we're their billing system, so their membership management and billing and payments.
So we're handling half a billion plus of payments through, across close to 1,000 customers.

Omer (03:02.810)
Great.
And can you give us a sense of the size of the business?
Where are you in terms of revenue, size of team customers?

Zak Holdsworth (03:08.750)
Yeah, so as mentioned, around about just slightly, 5,000 customers.
That's representing, you know, three quarters of a million lives across a few thousand doctors processing.
In terms of payments, you know, half a billion plus through the platform, we're about 35 people, about 40 people actually now.
And we are close to eight figures in revenue.

Omer (03:31.830)
And I think in terms of funding, you guys have raised what, about six, is it 64 million?

Zak Holdsworth (03:37.150)
So so far about 60.
Yeah, about 60 total across four rounds.

Omer (03:42.210)
So let's start with the idea for this business.
Where did it come from?
Do you have a background in healthcare?

Zak Holdsworth (03:50.370)
I didn't have a background in healthcare until the company before this, where I was at about three years.
I'd always been interested in healthcare, but more from a kind of personal human performance or personal health perspective.
But my experience at this last company really opened my eyes to how broken the system was.
And my favorite quote is it's like we're wasting about NASA about a trillion dollars a year in healthcare in the US which is NASA's budget since inception.
And NASA's done a lot of cool stuff that's a lot of money and that's every year it's wasted.
And we're not getting a good deal either.
Right.
It's 20% of GDP and it's half as good as a lot of other modern economies in terms of what you'd consider like quality or whatever.
And so when me and my co founder, we met at the last company and we thought, okay, let's go off and do something that we think could fundamentally transform this problem.
And so we spent a bunch of time, like two or three months looking at half a dozen or more ideas, trying to figure out like what are things that in theory, at scale could fundamentally transform the US healthcare system.
And the rubric we were using was there was a kind of intersecting Venn diagrams.
One of the Venn diagrams was, okay, if everything, if everyone in America had access to this innovation, would it address that trillion dollar problem?
Right.
Would it actually change the system versus would it just be incremental?
Innovation doesn't really change anything.
It just shifts money around.
So that was the first kind of circle in the Venn diagram.
The second circle was we want to build technology because we're kind of technologists and want to do a tech startup.
So that was kind of a part of that rubric.
And the third one was we want to be able to do something that we could move pretty quickly on and get into market fast.
Right.
We didn't want to have a business where it was like, hey, we're going to do a bunch of stuff and then in the future we'll make some money.
We wanted to make money day one, or maybe not necessarily day one, but like pretty fast.
And that was kind of how we were thinking about things.
And I would potentially, in hindsight, maybe change some of that thinking, but that's where we landed.
And okay, let's build this billing infrastructure for this.
There's a community of doctors that are stepping outside the broken system and redesigning it from first principles.
Let's build the software that they're currently using spreadsheets to handle their payments and things.
So that's where we started.

Omer (06:18.330)
I mean, anybody who's an entrepreneur certainly in the US knows from how difficult healthcare becomes once you leave a full time job and have to go and get it yourself.
And the same thing happened for me when I was working at Microsoft.
I didn't care about the healthcare thing.
It was all taken care of.
And then once I'm on my own, it was like, okay, well one option is paying $20,000 a year and a huge deductible and then you can get some healthcare.
Or the other option was like, well, what if you didn't have anything and you just pay out of pocket?
And then, you know, in the last few years I've sort of discovered this in between where, oh, there are these, you know, these doctors and these primary care providers who are going direct to patients and build this different model.
But it's still a very niche market.
And you know, as you know, you, you and I were talking earlier.
It's, it's one that's growing.
But why did you pick this in terms of, so you found a problem that you could solve, but I'm sure seven, eight years ago it was even

Zak Holdsworth (07:29.330)
much more smaller, more niche.
With this business, both my co founder and I, we truly were like, we're either going to do something that could transform the entire system from first principles, fix the problem, or we're going to not go do healthcare because let's go do something else.
We have lots of other interests, but the way I tend to think about it is that I think the healthcare system is so broken that it's simply not possible to fix it.
By just adding stuff to the current system like incremental innovation on top of the current system.
And so we knew it was going to be hard but we also saw a clear path.
It's like almost about eight years in now and the path is still the same.
I still see the same path.
It's just like oh, this is going to take a bit longer than I thought it would.
Which honestly if you're going to try to redesign the system from first principles, you probably should have realized you're setting up for a multi decade thing and if you're not down for that, don't do that.
That's a long time to be grinding.
And so it really just came down to I couldn't see and still to this day can't see another path that fundamentally transformed US healthcare and that doesn't involve redesigning from first principles, fixing primary care, stepping outside of the status quo, kind of chassis, fee for service infrastructure and like all of the legacy things that don't work and we know don't work and, and so we're still on the same path and so passionate about it.
But it's just a long journey and it's, you know, we're not necessarily in a market where hyper growth right is possible, at least right now I think it is possible at some point but it's not a typical like venture backed path and we kind of knew that a little bit going into it honestly.

Omer (09:27.360)
So, so how did you get started?
So you've identified a market, you think that there's a good problem and an opportunity for you guys.
What did you do?
Did you spend a bunch of time going deeper into that and trying to validate the idea?
Did you start building a product?

Zak Holdsworth (09:47.890)
It was interesting once we kind of identified this community of doctors that we thought okay, this could be almost like the way I tend to think about it is the sand with which the pearl will form around with which we could then start to transform the broader healthcare system.
And we're still on the forming the pearl phase by the way.
But once we had identified that and we thought this actually could be it, right and everyone's going to think we're crazy and it's totally non consensus and whatever else.
Once we had though committed, hey let's do something here.
We actually moved like lightning, right?
We went to the first conference in this movement.
We pretty quickly identified within a matter of weeks like hardcore cold calling, networking, flying around the country, you know, some early prospects and then we started identifying a problem.
My co founder actually started coding stuff like he was like, I'm going to start building something because we roughly know which direction we're going to head in.
And I started trying to close people on the promise of, hey, a product in the next few weeks, right?
So we actually generate within about 30 days.
We had our first revenue after we decided this is the thing, right?
You can do a lot in 30 days with a solid engineer and a solid salesperson that knows how to get stuff done.
So we generated our first revenue and had our first paying customer and our first user.
And if anything like the learning, one of the learnings I would have is if anything basically went too fast.
In hindsight, I probably would.
In Hindsight, it's always 2020 and maybe it wouldn't have worked out for the better, but if I had to go back and do things differently, I would probably have spent more time researching the customer and the problem than we did.
I probably maybe even gone in and worked in the doctor's office and for free even, right?
Hey, I'll be your admin for three weeks, right?
I'm going to go and like really sit down and study the problem versus just like striking, like striking like lightning on day one and just starting to build and sell and get something in market.

Omer (11:53.910)
I want to dig into that a little bit more because most founders would be super happy if in 30 days they've got their first paying customer.
And so people might look at your story and say, yeah, Zach's saying that, but it worked out okay for him not going deeper and taking his time.
So can you just help us understand why you say that now?
What problems did you have to deal with because you didn't spend more time going deeper?

Zak Holdsworth (12:23.130)
This is a 60, 40 thing.
I'm not 100% sure it would have been better to spend more time.
It's more like I think it would have if I was to give it another shot.
But I'd say the reason, the fundamental reason why is because, generally speaking, when you're early in building software and technology, everything's relatively easy.
It's relatively easy to stand up a product if it's simple surface, not a large surface area.
And it's real.
You know, if you don't have any constraints, right?
Like, it's like we can't do anything and build anything for anyone, right?
If you keep the surface area low because you're able to move so quickly, you can also move quickly kind of if the slightly in the wrong direction versus later, once you have customers and revenue and momentum and infrastructure and whatever else you put in place, the cost of changes actually goes up more and more and more over time.
So if that initial path you're on is like a little bit off, you end up spending quite a bit of time later on fixing the things that would have been relatively easy to figure out if you just spend a little bit more time thinking about it now.
So it's really just maybe I'd try to summarize as it's sort of a trade off thing.
Right?
You're trading off speed right now for kind of think of it as like product debt later and that might be the right trade off.
And in the early days that speed equated to, okay, we know there's a problem because people are paying us, right.
And they're using it.
So we got some insights there and there's value there.
But I think if you're thinking about that trade off, I think just know that it's not free.
Going fast does have some downsides and they may be the right trade off.
But that downside is that your cost of fixing the stuff you got wrong because you went too hard fast can be quite high later.
And if we had known all the things we knew even six months or a year in, I would say we'd maybe be potentially two years further along from a product perspective.
Right, because you have to take all that baggage with you through the journey.

Omer (14:32.850)
Yeah.
Because if you don't understand the problem deeply enough, then you may make decisions in terms of the way you build the product.
As you said, it's going to cause product debt later on.
And then also when you have a smaller set of customers, you're going to get requirements, which might sound like a good idea until you realize you just built a custom product for one customer.

Zak Holdsworth (14:54.340)
And customers never know what they want.
Right.
They think they know what they want.
But the classic if you ask them what they want, you'll be a bit of horse.
Right.
And carriage.
Right.
And honestly, I actually think we could have learned a lot by just, hey, I'll be your free admin working for your thing.
Let us, we'll work for you for free.
And you know, for a month like that that would have been so much more versus like, hey, what's the problem?
Oh yeah, right now, like I'm using a spreadsheet.
It's been a manual.
So if we look at this spreadsheet and then we're like, oh, we can automate that.
And so you automate the broken process they had versus like, what is the fundamental problem that you're trying to solve?
And like I'm going to solve it for you so I can really understand it authentically and really truly understand the underlying problems that surface into the broken spreadsheet you have.
And that would, I think just.
But there's a trade off, like you can't do that for two years, right.
Because you're not going to build business.
But doing, you know, more than one day where it's like, let's just start coding something is probably also the, the other extreme where it's like, you know what, maybe, maybe, maybe you go a bit slower.
Right?

Omer (16:05.860)
Yeah.
How long did it first customer in 30 days.
How long did it take you to get to the mythical first 10 customers?

Zak Holdsworth (16:12.820)
I'd say it was first 10 customers paying us something.
It's probably like three months or something.
Three, four months.
It's a little bit too far away for me to remember, but I'd say we, yeah, I'd say it's probably a few months, a quarter or something.
But again like they weren't paying us tons of, they weren't paying us tons of money either.
Right.
Our first customers, we actually had them on a percentage of transactions through the platform product.
So they didn't have to pay us any money out of pocket up front, which we changed at some point.
But yeah, it was.
Can be somewhat, a little bit hard to define what your first customer is because then maybe they're just kicking the tires because I didn't have to actually sign a contract or anything.
It was all click, wrap, got it.

Omer (17:05.050)
So basically you were giving the product for free to start using it.
And then there were kind of, there was a commission, transactional, whatever money they made, then you made some money.
So I guess that reduces some of the friction in terms of getting people on boarded.

Zak Holdsworth (17:20.890)
Yeah, but that was sort of the business model that we put in place on day one.
But the first, first customers, there was a couple, we actually went into their offices and they were like, oh yeah, I'm about to spend $20,000 customizing a Salesforce implementation so they don't have to use a spreadsheet or whatever.
And those customers, I actually said, hey listen, pay me the, pay me 15,000 and I'll custom build it for you from scratch.
But so, you know, she first month I had $20,000 contract, but it wasn't like recurring or anything.
It was just like will you pay me 20,000 to do this for you?
And another one was like 15,000 or something.
They weren't like SaaS recurring.
It was more think of as almost like consulting Projects and with a view that, hey, eventually we'll put you on our recurring revenue thing later if you're happy with the product.
But then once we started going down the path, then we started with, hey, put all your payments through hint, and then we'll just take 1% of all that and there's no upfront fee.
And so, yeah, there's a little bit less friction, but typically what we'd do is we'd try to sell them on, hey, but part of this deal is we're going to move all your patients to Hint right onto a platform.
So we'd kind of, we tried to validate that there was intention around that.
So it wasn't just a bunch of tire kickers, which is not a great thing for a SaaS company.

Omer (18:43.760)
What was the hardest thing about getting those first 10 customers to say yes?
So you, you took away kind of like the pricing objection.
I'm sure they were, you know, I, I imagine that these kinds of practices, there's a whole bunch of issues around privacy and HIPAA compliance that they kind of, you know, have to, to worry about.
And, and then potentially working with a startup where they don't really know there isn't a kind of a track record, maybe not as hard as selling to an enterprise customer, but I'm sure there was still some element of that.
So was it mainly those kinds of issues or were there any other problems that you had in terms of convincing these people to say yes?

Zak Holdsworth (19:29.490)
Yeah, all the stuff you mentioned was all true new people who are you, never heard of you before.
What do you know about our problems and all that stuff?
Right.
And actually one of the ways I would, the way around most of that was we are committed selling why you do it, not what you do.
Right.
Can't remember who it was.
It said that, I'm quoting, but it was very much, and this is still the case today vision, like, we believe that you are the solution to this problem.
We want to help support you.
We are very much aligned with you in terms of your mission and we want to work alongside you in achieving this mission.
Right.
And so that was the sales process.
And then it's like, oh yeah, we do some building stuff.
Right.
So that was how around a lot of the objection and a lot of that was through cold calling.
It's like, hey, we're entrepreneurs and we're looking to support this community.
Right?
And they're like, oh, wow, that's weird.
Like there's 80 of us.
And we're like, yeah, we know, but we still Exaggerating a little bit, but, like, you know, so that was it.
But I'd say that the more hard objections beyond that stuff was really, I'd say two things.
First was, gosh, that seems like a lot of work to migrate all my things into your product.
Right.
Like, I didn't even know where to start with that.
It's like payment information, some membership information, it's stored in multiple different places, blah, blah, blah.
Right.
So that was one piece, and the other piece was I'm.
If I.
If I don't get my payments next month because you fail, I will go out of business.
Right.
So, yes, your software helps automate all these different things.
My current process is broken, but it's not so broken that I'm going to not.
I'm going to go to business next one.
So, you guys, this new company, if this doesn't work and I miss a payroll, I'm done.
And these are.
Those are two big fundamental problems.
So the way we got through the first objection was we'll do it for free.
We will data mig everything for free for you.
And actually, we still do that today.
We've just got very good at it.
But at the beginning, it was a nightmare.
I was like, oh, my gosh, this isn't scalable.
But we started to see, okay, well, there's some patterns here.
And actually you get pretty good at it.
And once you've done it 10 times, then it gets easy kind of thing.
So that was how we got through that objection.
And people were like, oh, okay, cool.
The second piece was hard, honestly.
And literally in the early days, I remember one of our first customers, a guy called Dr.
Rob, he told me this story and I said, Dr.
Rob, if you miss payroll, I will personally guarantee that I'll pay your bills.
Oh, I will pay you whatever money out of my personal pocket that if we screw up.
And he went, oh, okay, cool, let's get started then.
And then I was like, oh, shit.
He said, yes.
Really, Graham, let's not screw this up.
So I was probably putting about 20k on the line, which is like a lot to a founder.
But also I'm like, you know what?
I'm 99% sure that we're going to get this done, especially if there's 20k on the line.
And so it was just a risk I was willing to take because if.
And then that problem over time went away.
Right?
If you've done it enough times, you got enough use cases and enough case studies and enough trust that you built in the community that Second problem went away, and we still continue to solve the first problem.

Omer (23:01.350)
Great.
So that gets you to the first 10 customers.
Did you raise any money at that point or were you bootstrapping up to the first 10?

Zak Holdsworth (23:13.270)
Yeah, we.
We raised money pretty quickly.
Once we kind of started onboarding customers, we started realizing, gosh, we probably should get another engineer and maybe hire someone and customer support, because Zach's going to be doing lots of product and sales work.
And so we're like, yeah, we don't want to put our own personal finances on the line because we're definitely way off from having the revenue needed, especially with our sort of premium model.
Right.
Where it's.
You scale with these clinics, they grow.
So, yeah, we went down the path of fundraising, and what was really interesting is I found the first round of financing was.
And I'd say generally the first year of our company, I found relatively easy.
Like, everything seemed to be easy.
It was like, okay, got our first revenue pretty easy.
We got a product to market.
It seemed pretty easy fundraising, you know, bunch of people that we'd worked with before or that really loved the vision or whatever, and we were able to get around.
Done quite quickly.
And it was a.
You know, initially I did 250k, and then we ended up expanding that to like 1.3 million.
And there's a few tricks I played along the way, but.
But the high level was that I found that first money was the easiest money, which was actually a little bit of a trap for me later because I thought it would always be easy, which obviously was probably just not a smart thing to think.
But.
But, but, yeah, we.
So.
And then we started hiring people and, you know, scaled the team up.

Omer (24:53.090)
Yeah.
So you've gone through, like, four funding rounds.
And I think a lot of people think, God, if I can just raise that first round or my angel round, I'm going to be good.
And you were saying, like, yeah, I've got to like, raising like, over $60 million.
And it keeps getting harder and harder.

Zak Holdsworth (25:07.670)
Yeah, it's not easier.
The running the business is not easier.
Like, you know, some stuff gets easier, obviously, but as a general rule, gets.
I found it harder and harder to fundraise.
Like, the bar goes up.
Right.
The.
When you have no metrics, there's actually an advantage because it's like, hey, risk a smart team, and we've got a big vision and whatever.
And, like, look at our other investors.
Like, clearly they know what they're doing, and so you get build momentum and you can actually play some tricks.
Like one of the tricks, I, it was not a trick, it was just generating momentum.
It's like we got an interview to yc and so I was talking to a bunch of investors like, hey, if we get into yc, the price is doubling.
And they're like, okay, we'll just do it now before you get into yc.
And then we actually didn't get into yc, but we got the money and the price didn't go up.
But I wasn't lying, it was all true.
And they knew what they were signing up for.
But risk adjusted, yeah, probably if they're getting an interview, they'll get in.
And so risk adjusted is the right move.
So small things like that, which we use, sort of simulating momentum, leaning on the other smart angels and getting intros from them and just building that pipeline and just closing it really quickly.
But what I found over time is that, you know, things started to get harder.
Right.
And I think for us, the fact that we were early in this nascent market caught up to us pretty quickly.
Right where we are now.
It's like, you know, what's your growth rate?
Yeah, it's still solid.
We're in the early days.
We're growing, you know, 80% a year or whatever, like, just like any other startup.
Right.
Like really fast.
But it's on a small base.
And so, yeah, I just generally found like running the company got harder, you know, and fundraising got harder.
And I think, yeah, so maybe I'll pause there.
But I think part of the thing I, you know, maybe before I pause, I think the trap I fell into is I assumed things would get easier and it was easy at the beginning.
And I was like, I'm just going to fly through this.
I'm a great founder.
I'm going to keep dominating forever.
But that was really a trap.
Like, in a way, I wish the first round was brutally hard and it would have trained me and got me ready for that.
It's always going to be like that.
I've pitched more than a thousand investors in this company, you know, to get that money.
1,000.

Omer (27:37.020)
You pitched to a thousand investors to get which money?
Like through the process.

Zak Holdsworth (27:42.380)
Yeah.
Over the lifetime of the company, I've pitched a thousand investors.

Omer (27:46.540)
Wow.

Zak Holdsworth (27:46.940)
Some pitch might be a 15 minute thing, elevator pitch.
Some might be a full partner meeting, the whole shebang.
But I've had that many meetings, one with unique individual funds, because you would,

Omer (27:57.980)
you would think once you've started to raise that end round or the first round, you'd only have to Have a few conversations because you're building a track record and credibility and whatever.
So what was going on?
Why did that happen?

Zak Holdsworth (28:09.530)
Yeah, I'd say that at a fundamental level, this saying it doesn't matter if you're right, but your timing is wrong, that's the same as being wrong.
At least right now you could still be right later, but right now you're wrong because your timing's wrong.
And so I think the thing that made it really hard for us is total addressable market is not big enough.
And venture investors, even though if you look at most of the big iconic 100 plus billion dollar companies, they all started with no markets that they created, blah, blah, blah.
Even with all of that, you know, if the total addressable market you're targeting is not big enough, then investors, it's hard to convince them to give you money.
Now the way that's manifested itself in this business is I've got the money, but I've just had to get more dilution.
But now what's interesting is we're coming around the corner.
We sort of survived.
Like one of the things I think is almost like an axiom, axiomatic truth.
It's like the, the founders that will succeed on average, obviously there's outliers where there's people that just dominate and create $100 billion company in four years or whatever.
That's like most companies aren't that.
But if you take the rest of that sort of bell curve of outcomes, the ones that end up in the upper quadrant are the ones that don't give up, don't die.
Right?
Don't be a zero if you can stick around long enough.
Now there are some counter arguments to this, like, well, if you're doing the wrong thing, maybe you should kill what you're doing purposefully.
But if you want to, if you believe in what you're doing and you want to get there, don't give up at any cost and just keep grinding.
And that's what we've done at hint.
And I would say the way that that sort of market size problem has manifested itself because I believe we're right.
We were just very early, but it was manifested itself is we have less ownership in the business.
But I'm okay with that because we're not about making money.
Like, yes, I want to make money, but it's not the primary thing that drives me.
Right.
Oh, if we have a outcome of the size that I think is possible, given the transformation that we think we can be part of driving, I'll Be fine for money, right?
Probably won't have a billion dollars, but I don't need a billion dollars.
But if that's your goal, then I probably wouldn't do mission first, right?
In the thing you're doing.
Like, if your goal is to make a billion dollars, don't follow my path.
It's probably not the best way to do that.

Omer (30:52.110)
Yeah, yeah.
I spoken to a serial entrepreneur who's had several successful exits and I think he said something once like 5% of a billion dollar company is better than 100% of a company making no money.
Right.
So that's kind of also one piece to look at it.
But it strikes me that what you said there, the thousand pitches to investors, the kind of drive to keep going, a lot of that boils down to the mission.
Now a lot of the times when we talk about missions and vision statements and all that stuff, it's just a bunch of, you know, hand wavy kind of stuff that doesn't really mean that much.
Yeah.
But if you really are like, you know, you're kind of this business where you're like, hey, I'm driven by really making a difference here that's going to give you a lot more endurance and stamina to keep going than I'm driven by building a SaaS business that makes money.
Right.
You probably go move on and do something else, right?
Because it's like, yeah, I can find a bigger market and the investors will love me.

Zak Holdsworth (32:11.990)
Now I'd say that's completely true.
And that's, I'd say is permeated throughout the organization.
Right.
Like, people join.
A big part of the reason people join us at HINT is because of the vision and mission.
And we've actually got, we've even had to coin a term for people that have left HINT and come back.
We call them the Hint Boomerangs because they're like, they'll, they'll leave, they'll see more shiny objects somewhere else, you know, leave.
And then I'll realize shit like HIND actually had meant something.
It meant something to work at hind.
Right.
We actually were changing the world, right.
In our small way.
And it was.
And we had a strong culture and it really built great community within our customer base and so on and so forth.
And so yeah, if we didn't have Mission, if we like, I would have given up.
I can't remember how long I've been doing this, but it's like eight or nine years or whatever.
I would have given up seven or eight years ago because it's like once it started getting hard.
I would have said, you know what?
This is.
This is maybe not the right thing.
The other maybe you'd made a point earlier, just in terms of the one that the gentleman had said, hey, I'd rather have 5% of a billion dollars than 100% of zero.
Right.
And I agree with that, obviously.
But there's also a counter to it where some of the most successful entrepreneurs I know financially held 80 or 90% of a $30 million business or $20 million business.
80% of 20 million is 16 million.
I don't know what everyone's number is, but that's like, I don't need more than that personally.
Right.
And I personally don't have a desire to be able to say, oh, I have a billion.
I'm a founder that created a billion.
So I think that the, you know, maybe the point I'm trying to make is, like, be trapped in.
As an entrepreneur, I think it's really important not to be trapped in, like, the Instagram post or the equivalent of social media, where it's like, everything looks perfect.
Don't let that be the thing that drives you, because you're not going to be happy if that's what drives you.
It doesn't work because you get to a billion and then there's a guy that's got 10 billion and you feel like an epic failure because he's an order of magnitude.
Then you get to 10 billion and there's a guy with 100, and you're never going to be happy if the number is what is driving you.
And so, yeah, it's like, what's the right path for you?
It's like, it's financial independence.
It's important.
Great.
Well, you don't need to raise a lot of money necessarily, to do that, but that could be the path as well.
But with money comes some risks, you know, like, there's some downside to money.

Omer (34:53.640)
Yeah.
It reminds me of this episode of Fraser I saw years ago.
Like, you know, Fraser and his brother Niles there, that they get into this health club, it's this exclusive thing, and they keep seeing this door that other people are going into, and they're like, what is that?
And that's the VIP thing.
And then they just, like, are just obsessed.
Like, all they want to do is figure out how they can get through that door, and that's what the whole episode is about.
And, you know, eventually, like, you know, they do a whole bunch of kind of shady things.
They get through and they think they're over the moon because they made it into the VIP area, and then they realize there's another door for another VIP section that they kind of obsess and waste time about.
So it's the same thing.
Right?
You're never going to be happy if you're always chasing something like that.

Zak Holdsworth (35:41.860)
And once you get into the VIP section, it's not that.
Sometimes it's not as good because there's not that many people and you can't dance on the dance floor or whatever.
It's like, she needs to leave here and go back to the normal.
In hindsight, we're actually pretty content with where we were.

Omer (35:57.510)
Yeah.
Yeah, totally.
So we talked about getting to the first 10 customers.
Let's talk about the first hundred.
What did you do?
Was it still just a lot of hustle, cold calling, meeting people, or once you had the first 10, 20, did you start to take a different approach to growing the business?

Zak Holdsworth (36:18.160)
Yeah, I'd say the first hundred was, you know, still a lot of hustle.
Right.
Like, and it was cold calling, networking and things like that.
And, you know, we did some content stuff.
We were hosted webinars.
We.
This is probably post 100 customers, but we launched our own conference, which was a.
Which we could talk about if there's interest there.
Um, but I'd say, yeah, it was, it was, but it was leaning on.
I think the, the nuance was that we were leaning on the success of.
And the word of mouth that we were starting to generate.
Right.
And some of the successes we were, we were building there.

Omer (37:01.220)
Yeah.
Because every time you're.
You're getting a customer on board, you're.
You're getting more and more social proof now.
Okay, so let's.
So 100 is a hustle.
Let's talk about the first thousand.
So the next kind of like, level.
I know one of the things you focused a lot on was thought leadership.
What does that mean?
Was that around content marketing?
Was that around the event?
Was it around something else?

Zak Holdsworth (37:29.940)
I'm not even sure if we've crossed a thousand yet.
Right.
I think we're close to it.
Right.
Because one of the things that happened is our clients got bigger.
Right.
So we started small, but as they grew, we grew with them and we started building cadence around larger and larger deals and built more features to support more sophisticated networks, things like that.
So there was an element of, you know, our customer got larger, which is, I think, is important in SaaS.
But in terms of kind of getting from that 100 to 1,000 order of magnitude, for us, it Was, you know, primarily around increasing, ensuring we create a really amazing experience for our customers, really great customer support, really supporting them as many ways as we can, really listening to like kind of what their core needs are and continue to support them.
And I'd say a lot of our business started pivoting to word of mouth and kind of inbound remarketing inbound referrals from either customers or partners.
And so I'll break that down a little bit.
One of the strategies we deployed is we started partnering with other tech vendors that were serving the same community.
There weren't too many of them, but we built integrations with them and would go to market with them.
So we all might refer some business to you, you refer some business to us, we're going to do better together.
You're an electronic medical record, we're a billing system.
We'll refer leads to you and vice versa.
So we got business from that, but we also got business because our customers had such a profound experience with us and they saw the sort of authenticity we had with this market that they would start referring customers.
And so even today, a lot of our small to medium sized deals come inbound.
So what we started to do is, okay, are there ways we can kind of amplify that, right, that, that sort of brand halo and trust and fierce loyalty.
What are the things we can do to lean into that growth strategy?
Because it's the main thing that's working.
And so we launched our first summit, which is an annual conference.
And I invited, you know, about 120 people and about 120 people showed up.
Right.
I'll probably, maybe I invited 50 people, but I personally reached out, I organized the speakers, I organized the venue, we got great food, we tried to do something unique and different.
I made it about, I made it about the, this community and, and, and, and people, you know, signed up and they came and we actually sold out and had the fire code reached the FICO.
It was about 100 people in the space we're in.
We breached it essentially.
We did stuff like that.
We experimented with content marketing.
We would do like, we'd interview doctors and do blogs with them.
We would try, do you know, the occasional webinar.
We would bring someone in that's got interesting insights.
Eventually we turn that into actually our DPC Direct Primary Care Accelerator program where it's actually a free service we give to our customers.
Where it, if you're part of our community then you'll get free education and free content and free webinars.
And so people Talk about that.
And that becomes a way that people come to us.
And the other thing we did is we started experimenting with clients would start to.
They're starting to build networks.
So we built features that enabled them to manage those networks in hint.
So there's actually an element of kind of a network effect that happens with our product where one doctor will actually invite another doctor.
I'd say that's not the main growth driver, but definitely does.
It's a form of that referral pathway of an inbound lead that comes to us, develops that relationship with us and then eventually converts to a customer.
A lot of those strategies are still in play today.
They're just bigger scale.
So it's a lot the same stuff that is working, we scaled it.

Omer (41:29.330)
Did you charge people to attend the event?

Zak Holdsworth (41:33.280)
Yeah, we did, we charged.
Our goal was let's just break even.
So I think in the first event, so I was like $150 or something to come and then if you didn't get a ticket early it would be 250 or something like that.
And I've always tried to keep that event affordable.
And we've never, the intention has never been a money maker.
It's just been let's break even on this.
And our last event we had know 450 people or something post Covid.
We're actually hoping for more than that.
And people were paying anywhere from 350 to 550.
And I anticipate that trend continuing.
Right.
The, the cost will go up a little bit because we'll maybe go a little bit bigger, bring more people in, bring bigger keynotes.
Because I always try to bring some unique keynotes and get more people to attend.

Omer (42:20.730)
And then is this mostly customers attending or are you trying to get this as a way to reach out to new potential customers as well?

Zak Holdsworth (42:29.380)
I see this event as actually an industry event versus a user conference.
And so it's more about what do we need to do as an industry to succeed.
Right.
It's more about the mission.
Turns out that half the people at the conference are hint customers.
And it also turns out that about half the people in this industry our customers.
Right.
Maybe not exactly that, but it's roughly so in a sense it's an industry conference, but we have a lot of the industry and.
And so.
But we definitely use it as a way to.
I found it's very powerful from a sales perspective.
If you're in a conversation with someone, you invite them to the event and they'll have a good time.
You meet Them in person definitely helps close the deal.
It reinforces we are here to support this community.
Right.
My keynote is a big part of that.
It's like this is why we exist.
I always talk about our mission and why we exist and what we do and why we do it.
And that resonates right with people.
And then we also have prospects and we also have partners.
So it's a way of making sponsoring.
So if you want to be part of our annual conference, you need to be a partner.
And in order to be a partner, we need to figure out how to create value for this community together.
And what does that look like?
And so it's a little bit of leverage as well around, hey, if you want to be part of this community, this conference, we need to figure out a way to work together in a way that creates value for people.
So it becomes a BD driver as well.
We actually turn away more sponsors from that conference than we accept as sponsorship.
So we're turning away money because people want to be part of that, that community.
So that's the mix, I guess.

Omer (44:16.100)
So.
One more thing I want to talk about before we wrap up here is we talked about some of the challenges you had with investors and the total addressable market.
And on the one hand you've stayed true to that mission and you know, not kind of compromised or gone down a direction which maybe would have, you know, given you a faster growing business or a bigger, bigger, total addressable market.
But you have also tried to move horizontally into different areas and that has something that you haven't been able to kind of figure out or crack.
So can, can you just give me an example of what, what you've tried there and what were some of the challenges that you faced?

Zak Holdsworth (45:08.100)
Yeah, I'd say that the, you know, We've got a core kind of direct primary care segment and we've spoken a bunch about that.
But there has been points in time where we've said, okay, can we succeed in other segments but with a similar software like are there, you know, other verticals in healthcare that need like a membership management system and that and could use our software because we built that and there are, and we actually have a number of clients that have come to us saying, hey, I'm not DPC but you know, I'm a membership based thing.
Can we work with you and absolutely sure you can, here's the software, we'll support you.
What I've found is that, or if you're employee direct contracting, you know, there's some other non kind of primary care segments that we support.
What I found is that, okay, well if there's some, if there's a few that are coming to us, maybe why don't we spend a bit of resources to scale that?
Because that could help fund our mission, right?
If we get these other segments to pay us money.
What I've found is that the sort of, That sort of transition to new segments is in a way you almost, I think, underestimate all the things you've done to have success in the segment that you're successful in.
And what I mean by that is it's like, okay, well if you're going to go and sell into this other segment, you either got to build an outbound engine, which we have a semblance of, but it's not where most of our business comes from in our core segment.
So you got to either build out an outbound engine and all the sales, enablement, materials and collateral and everything that would speak to those Personas and all that work, that kind of sounds easy, but it's actually like real work, or we have to go build the authentic mission driven community kind of inbound marketing referral engine that we've built in the community that we're successful in.
And that's also hard and takes time.
And so it's not to say we haven't had some success in other verticals in healthcare is just that they don't scale as easily as you would anticipate without all of the foundational work that goes into scaling them.
And if it's not the core focus of your business, the cost of dabbling there may be not necessarily worth the juice that you squeeze from it.
So that would probably be the learning there for us.

Omer (47:45.350)
And so is that something that you're still trying or testing in different areas or have you kind of just moved on from that?

Zak Holdsworth (47:54.110)
I'd say we still are testing.
I'd say that the testing though is more what we try to figure out is, okay, what is critical path long term and are these segments part of that?
Right?
And if they are, what's the sequencing here?
Can we bring that sequencing forward a little bit or not?
And you know, and is that.
And so we're.
One example of this would be we have, you know, the small independent DPC clinics.
We also have larger independent direct primary care clinics and network and they primarily work with employers.
And there's a lot of similarity from a cultural perspective there.
And so it's like, okay, we can serve both those communities, but then there's like the sort of next segment up which is like I don't really self associate with direct primary care, but I am direct contact with employers and like a near site, on site clinic group.
So maybe I don't necessarily self associate with this community but I have at the end of the day the same long term objective.
And so we are paying more attention to that segment and trying to because we got a bunch of features and capabilities that could serve that segment.
So we're doing so within the context of this needs to be part of the solution long term because this is versus random segment that seems interesting as a way to make money.
We try to put it on critical path so that we don't end up kind of straying too far from our sweet spot.

Omer (49:31.110)
Great.
Okay, we should, we should wrap up, move on to the lightning round.
I've got seven quick fire questions for you.
Are you ready?

Zak Holdsworth (49:42.640)
Yes, I think I'm ready.

Omer (49:48.160)
What's the best piece of business advice you've ever received?

Zak Holdsworth (49:51.360)
Focus, Maniacal focus.

Omer (49:54.880)
What book would you recommend to our audience and why?

Zak Holdsworth (49:57.840)
In the early days of Hint, I found Lean analytics to be really helpful.
And the reason I found it helpful is it really helped me think through how do you define what.
What are the key things we should care about from a metrics perspective and how do we measure them and how do we.
And how do we let go of them when the time is right to let go of them?
Right.
And that sort of sequencing of how do you focus your energy in the right parts of your business to kind of get you to the next stage.
So I found that book really helpful.

Omer (50:33.970)
What's one attribute or characteristic in your mind of a successful founder?

Zak Holdsworth (50:38.850)
Build a culture that's authentic to you because it's too hard to fake it.
So if transparency is not a thing you're good at, naturally don't have it as a value.
If it is, have it as a value, and so on and so forth.

Omer (50:50.050)
What's your favorite personal productivity tool or habit?

Zak Holdsworth (50:54.070)
I should have a really good answer to this, but what I was going to say was like hire really amazing people so you can delegate things.
But that's a cheat.
That's cheating.
That's not your question.
I'd say, but I'd say that probably the one, my favorite one is probably like traitless.
You know, just.
And if you, if you feel like you're not sure what the right direction is, sit down and just build a big long list.
And just that process by itself will help you clear your thoughts and triage.

Omer (51:34.290)
What's a New or crazy business idea you'd love to pursue if you had the time.

Zak Holdsworth (51:37.410)
If I could do something now, I would consider jumping into the.
Creating more fuel efficient transport, like flying transport.
Like you have, you know, drones you can sit in and like get from go, you know, line of sight, fully autonomously.
Like Uber, basically a quadcopter Uber.
Right.
That would be something I think is definitely going to happen.
It's.
That would be something I would probably look at.

Omer (52:05.910)
I think I heard about something like that happening and I think they were trying to do that in Dubai somewhere.
Like passenger.

Zak Holdsworth (52:12.080)
Yeah, I think it's happening.
Yeah.
It's just a matter of time.
And then you would solve a bunch of pretty interesting problems with that, like societal problems if that became mainstream.

Omer (52:24.560)
What's an interesting or fun fact about you that most people don't know?

Zak Holdsworth (52:29.120)
I was missed in New Zealand.
I was the most eligible bachelor in New Zealand in 2002.
Wow.

Omer (52:38.290)
What was that?
Is that an event or some magazine thing?

Zak Holdsworth (52:42.650)
Yeah, like a magazine thing, kind of like an event, you know.
Yeah.
And you know what was interesting about it is I think the reason I won is because it was the first year they had email voting and I was at uni and basically some.
One of my friends submitted me to it and then it went viral through the email list servers and like all of our everyone at uni voted for me.

Omer (53:06.470)
And finally, what's one of your most important passions outside of your work?

Zak Holdsworth (53:09.670)
You know, a few years ago I would have said, you know, kite serving, adventure sports, like being out in the outdoors.
And that's all still true but you know, it's a bit cheesy but like I had a lot of joy for my.
I've got a young family, so I have two little girls and just you know, watching them grow and develop, it's like super fun.
And then my third answer would be, I love playing board games.
Right.
And like I don't do it much.
I'm actually looking forward to my girls being older but I love like sitting down around table and playing like Risk or catan or chess or something or cards or whatever.
I just love that and I feel like that's somewhat been lost in today's day and age because everyone's on their machines, right.
And something nice about the real world.

Omer (53:54.010)
I've been getting into board games with, with my family over the last few years as well and it's nice just, just to do that.
So if we ever meet up, I'll bring some board games with me.

Zak Holdsworth (54:03.850)
Sounds good.
Play

Omer (54:07.130)
awesome if people want to find out more about Hint, they can go to hint.com and if people want to get in touch with you, what's the best way for them to do that?

Zak Holdsworth (54:16.570)
LinkedIn.
You can hit me on LinkedIn or you can email me.
You can email me@zintz.com if you want.
But if you cold email me, though, without an Intro, there's a 50, 50.
I'll answer.
You know, best way to get to is find someone that knows me and ask for an intro.
And I pretty much never say no to intros, but I mostly just archive random cold emails.

Omer (54:40.850)
Awesome.
It's been a good conversation, man.
Thank you for joining me and kind of talking about the last eight, eight, nine years.
I think there were some really interesting things that you shared that were very thoughtful.
It's one of these interviews where I feel like I'm going to go back and there's a bunch of things that I can kind of listen to and sort of think more about and kind of just maybe even kind of just write about it or something.
But there's some really interesting lessons there that you shared.
So thank you for doing that.
I love what you guys are doing.
I love the mission.
Personally, as a consumer, I was looking at direct primary care in the last couple of years and kind of wondering if I was kind of brave enough to kind of take the leap and do something different to what 90% of people are doing in this country.
And, yeah, I think it's an exciting area.
And often when we look at sort of healthcare, most people will say, somebody's got to do something about this.
And so it's inspiring to see that you guys are actually walking the talk.
So wish you all the best and I hope that what you're doing is a tremendous success for everyone in that community and that a lot of people get benefit from that.
So thanks again and wish you and the team the best of success.

Zak Holdsworth (56:11.500)
Thank you so much.
And yeah, and thanks for having me and pulling all those supposed insights out of me and happy to chat anytime.

Omer (56:21.580)
It's my pleasure.