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Home/The SaaS Podcast/Episode 389
How Narrowing Your Niche Can Reignite Stagnant SaaS Growth
Brennan Dunn, RightMessage

How Narrowing Your Niche Can Reignite Stagnant SaaS Growth

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Episode Summary

Brennan Dunn raised $500,000, grew RightMessage to $35K MRR in a year, then watched it all slide backward. For two years, growth flatlined and both co-founders lost motivation. The SaaS positioning was too broad, customers lacked the data the product needed, and the money ran out.

In this episode, Brennan reveals how he bought out his co-founder with personal savings, narrowed the target market to online creators, and used hands-on consulting to land customers like Justin Welsh and Pat Flynn - reigniting growth after years of stagnation.

In 2017, Brennan Dunn turned a zip file of JavaScript code into a SaaS product called RightMessage. The tool helps website owners show personalized content to visitors based on their email marketing data - changing headlines, CTAs, and offers depending on who is looking.

The founding story had all the right ingredients. Ankur Nagpal, the founder of Teachable, pushed Brennan to build the product and helped organize a $500,000 seed round from friends and investors including Nathan Barry. Within a year of launching in early 2018, RightMessage hit $35,000 in monthly recurring revenue.

But the growth masked a SaaS positioning problem. RightMessage was targeting everyone - SaaS companies, e-commerce stores, creators, even plumbing companies. Many customers signed up excited about website personalization but lacked the segment data needed to actually use the product. Without the "if this" part of the equation, the tool couldn't deliver its promise.

The team burned through the funding faster than revenue could catch up. Growth stalled. MRR declined below $20,000. Both founders got demotivated and stopped investing energy in the product for nearly two years.

The turning point came when Brennan bought out his co-founder and made a critical SaaS positioning decision: stop selling to everyone and focus exclusively on online creators doing seven and eight figures in revenue. Instead of hoping customers would figure out the product on their own, Brennan offered hands-on consulting to implement RightMessage for high-profile creators like Pat Flynn, Justin Welsh, Matt Gray, and Dan Go.

The results were immediate. Justin Welsh saw a 38% increase in course launch conversions using RightMessage. The "Powered by RightMessage" badge on these creators' websites started generating inbound leads. And Brennan built something he never had before - real case studies with specific revenue impact.

Now Brennan is using that credibility and consulting revenue to rebuild the self-serve experience, while pairing the software with educational courses as a growth engine - the same playbook Nathan Barry used to grow ConvertKit.

Topics: Positioning & Differentiation|Churn & Retention

Key Insight

Brennan Dunn grew RightMessage to $35K MRR in its first year, then watched it decline for two years because the product targeted too broad a market. After buying out his co-founder, he narrowed SaaS positioning to online creators and used personalized consulting to land high-profile customers like Justin Welsh, who saw 38% higher course conversions - turning stagnation into renewed growth.

Key Ideas

  • RightMessage hit $35K MRR within 12 months of launch, then declined below $20K MRR over the next two years due to broad targeting
  • Customers signed up for website personalization but lacked the segment data to use the product, creating an onboarding gap
  • Brennan bought out his co-founder using personal savings after the team burned through $500K in seed funding
  • Narrowing from "anyone doing email marketing" to pro creators doing $1M+ per year made the product's value proposition clear
  • Offering paid consulting to implement RightMessage for flagship customers like Justin Welsh generated 38% higher conversions and built credible case studies

Key Lessons

  • 🎯 Narrow your SaaS positioning when growth stalls: RightMessage targeted everyone from SaaS to plumbing companies. Growth only returned when Brennan narrowed to pro creators doing $1M+ per year with clear use cases.
  • 🤝 Use personalized onboarding to land flagship customers: Instead of waiting for self-serve adoption, Brennan offered paid consulting to implement RightMessage for high-profile creators - turning an onboarding weakness into a relationship-building strength.
  • 📉 Hiring ahead of revenue kills bootstrapped momentum: RightMessage burned through $500K in funding by scaling the team before revenue could sustain it, forcing painful downsizing and two years of stagnation.
  • 🚀 Leverage influential customers for SaaS positioning credibility: Landing Pat Flynn, Justin Welsh, and Matt Gray gave RightMessage the case studies and "Powered by" visibility it needed to generate inbound leads organically.
  • 💰 Pair educational content with SaaS positioning for growth: Brennan bundled a segmentation course with RightMessage credits, using education as the gateway that brought prospects to the software without traditional SaaS marketing.
  • 🧠 Invest in relationships before you need them: Brennan's $500K seed round came from friends like Nathan Barry and Ankur Nagpal. His flagship customers came from years of genuine relationship building at conferences.

Watch the Episode

Chapters

00:00Introduction
02:45What RightMessage does
04:18How website personalization works with email data
06:40Predictive intent and the Netflix personalization example
08:42Business metrics: $20K MRR, 250 customers, team of 3.5
10:50Origin story: from JavaScript zip file to SaaS
13:31Raising a $500K seed round through personal network
15:24Launching in 2018 and hitting $10K MRR in month one
18:00Growing to $35K MRR then hitting the wall
20:08The onboarding gap: customers lacked segment data
21:41Burning through funding and downsizing the team
24:01Two years of stagnation and losing motivation
25:21The Hail Mary rewrite that failed
27:30Buying out the co-founder with personal savings
29:00Personalized onboarding for flagship creators
30:42From software as a service to software and a service
31:20The ConvertKit playbook: landing Pat Flynn first
33:17How the first deal with Pat Flynn happened
35:32Landing Justin Welsh, Matt Gray, and Dan Go
37:48Using courses as a SaaS growth engine
41:02Why creators over SaaS companies as target market
44:26Choosing a market you want to spend 10 years in
46:04Lightning round
50:14Wrap-up

Episode Q&A

How did RightMessage grow to $35K MRR in its first year?

Brennan Dunn treated the SaaS launch like a digital product launch, using urgency-based pricing and his existing email list of 3,000-4,000 people to drive initial signups. RightMessage hit $10K MRR within the first month and grew 20% month-over-month to reach $35K MRR within a year.

Why did RightMessage stagnate after reaching $35K MRR?

The SaaS positioning was too broad - RightMessage targeted anyone doing email marketing, from SaaS companies to plumbing businesses. Most customers lacked the segment data needed to personalize their websites, so they signed up but never activated. Growth stopped and MRR declined below $20K.

How did Brennan Dunn's SaaS positioning shift save RightMessage?

Brennan narrowed the target market from "everyone" to online creators doing seven and eight figures per year. These customers already invested heavily in email marketing, understood audience segmentation, and had portfolios of courses and coaching products that benefited directly from personalized messaging.

What onboarding strategy did Brennan Dunn use to land influential RightMessage customers?

Brennan offered paid consulting where he personally implemented RightMessage for high-profile creators. He told prospects they could pay for his consulting fee and he would configure the tool himself, removing the friction that had blocked self-serve adoption.

How did Justin Welsh's use of RightMessage generate measurable results?

RightMessage helped Justin Welsh increase overall conversions for his course launch by 38%, translating to hundreds of thousands of dollars in additional revenue attributable to the personalized messaging the software delivered.

Why did Brennan Dunn buy out his RightMessage co-founder instead of selling the company?

Brennan had previously sold his first company, PlanScope, and the new owner drove it into the ground, hurting Brennan's reputation. He did not want to repeat that. He also did not want to shut down and abandon the 150-200 paying customers who relied on the product.

How did RightMessage use the ConvertKit growth playbook for SaaS positioning?

Just as Nathan Barry landed Pat Flynn as a champion customer for ConvertKit, then approached Pat's peers, Brennan landed Pat Flynn and then recruited Justin Welsh, Matt Gray, and Dan Go. Each new flagship creator generated inbound leads through the "Powered by RightMessage" badge on their websites.

What role did educational content play in RightMessage's SaaS positioning strategy?

Brennan paired RightMessage with a video course on email segmentation, offering a purchase credit equal to the course price toward a RightMessage subscription. The course served as a top-of-funnel growth engine, educating prospects on why they needed segmentation before pitching the software.

Why did Brennan Dunn avoid enterprise SaaS positioning for RightMessage?

A Fortune 500 company found RightMessage and Brennan spent 20+ hours on calls that never converted to revenue. He decided enterprise sales - with its long cycles and custom feature demands - conflicted with his preferred operating model of self-serve pricing and small team autonomy.

Book Recommendations

Badass: Making Users Awesome

by Kathy Sierra

Links

  • RightMessage: Website | LinkedIn | X
  • Brennan Dunn: Website | LinkedIn | X
  • Omer Khan: LinkedIn | X
Full Transcript

Omer (00:09.760)
Welcome to another episode of the SaaS Podcast.
I'm your host Omer Khan and this is a 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 Brennan Dunn, the founder of right message, a SaaS product that helps increase conversions by showing website visitors the right message at the right time.
In 2017, Brennan and his co founder decided to turn a JavaScript library Brennan had built for his email marketing course into a fully fledged SaaS product.
They managed to raise $500,000 thanks to Brennan's existing network and relationships from his previous successful ventures.
The product launched in early 2018 and quickly grew to 35,000 in monthly recurring revenue within the first year.
However, the founders soon started experiencing problems.
Firstly, customers were struggling to implement the product and didn't have the pre existing data that the product needed.
Secondly, the founders hired quickly leading to a high burn rate and eventually running out of money.
As a result, the business stopped growing and and struggled to get new customers, forcing the founders to downsize the team.
The lack of progress also drove both of the founders to lose motivation and start focusing on other projects instead.
Eventually, Brennan bought out his co founder using his personal savings and started to focus on rebuilding the business.
He narrowed his target market to online creators this time, and by offering personalized onboarding to land influential customers and build credibility, Brennan has managed to start turning things around.
After years of stagnation, the business is growing again.
In this episode, you'll learn how Brennan overcame a period of stagnant growth and demotivation by narrowing his focus to a specific niche and rebuilding his product.
Why?
Doing things that don't scale, like personalized customer onboarding, can be a powerful strategy for reigniting growth.
And In a struggling SaaS business, we talk about how leveraging founder relationships and targeting influential customers can unlock growth opportunities for your startup.
What strategies Brennan used to lower friction for new customers and expand his top of funnel leading to a resurgence in growth and why.
Building a business that aligns with your desired lifestyle and making time for passions outside of work are essential for long term founder success.
So I hope you enjoy it.
Brennan, welcome to the show.

This Is Personal: The Art of Delivering the Right Email at the Right Time (02:45.440)
Hey, thanks Omer.
Thanks for having me.

Omer (02:47.200)
Do you have a favorite quote?
Something that inspires or motivates you that you can share with us?

This Is Personal: The Art of Delivering the Right Email at the Right Time (02:51.200)
It's not a quote, but it's something I kind of learned the hard way early on which has stuck with me ever since, so.
And that is, no one's ever Paid me to code.
And this is something that has carried over to my product days where I think if you're like me and you're a technical kind of founder, you get obsessed with the features, you get obsessed with the building of it, the architecture and all that stuff.
And the thing I had to really.
It's still one of these things I struggle with constantly is the realization that I learned way back when I used to do a lot of consulting was clients didn't hire me for code, they hired me for business benefit.
Right.
So that's kind of my like, I'm not a quote person, but that's my grounding thing that I'm always like, if I could put that on a wall, I should.
But that's what should be there.
Because I do get distracted by rabbit holes of code and architecture and all that stuff that is important but ultimately isn't.
When people buy.

Omer (03:47.250)
Yeah, no, I love it and I think I'm very much like you.
I find that coding is a great way to just disconnect, do something.

This Is Personal: The Art of Delivering the Right Email at the Right Time (03:59.810)
It's therapeutic.

Omer (04:00.850)
Yeah, therapeutic, yeah.
Many people would think we're insane, weird, insane.
But yeah, there's something definitely there if you're built like that.
So tell us about Right message.
What does the product do, who's it for and what's the main problem you're helping to solve?

This Is Personal: The Art of Delivering the Right Email at the Right Time (04:18.510)
Yeah, so we help companies that do a lot with email marketing better understand, segment and personalize their email list.
So we tend to work with nowadays mostly creator type people.
So we call them procreators, which would be not procreators but pro space creators who are doing seven, eight figures a year, usually selling courses or coaching.
But we also have a smattering of software businesses, media brands and even agencies who use us.

Omer (04:47.380)
Great.
So maybe just explain a little bit how the product works because there's different components to this.
There's the experience that people get when they visit the website, there's integration with whatever email service provider you may be using.
There's some level of personalization that gets delivered on the website.
So maybe just describe what that experience looks like and which parts of that is driven by Right message and which parts are kind of supported.
Like, you know, the email marketing piece.

This Is Personal: The Art of Delivering the Right Email at the Right Time (05:24.770)
Yeah, good question.
So we're, we're easiest thought of as a bridge between your email platform and your website.
So what that means, tangibly, is if somebody from your list goes to your website and you segment them as like a customer, so they're tagged with customer or whatever else, that data gets pulled to your site.
And then you can make changes on your website depending on that.
So, you know, for example, you could say like if a returning email list subscribers back on your website don't show email opt in pop ups.
Right?
Like don't show the pop ups, show a sign up for a trial, call to action if they haven't started a trial or they're not a customer.
Likewise, you can also do things like changing out logos depending on what industry they're in, or showing a different case study or something like that.
So we make it really easy to pull data down and also to collect data through behavior, like what pages they're visiting, what ad campaigns they came from, what kind of content they're reading.
The most of what affiliates sent them along with what we call zero or not we call, but what the industry calls zero party data, which would be serving.
So, you know, we can collect this data and then send it right back up to the email platform, which you can then use for future interactions on the website or to then send better, more targeted email campaigns.

Omer (06:40.810)
Got it.
Yeah.
I was reading something about predictive intent the other day and it sounds like that's basically what you're helping to achieve in terms of figuring out when people are most likely to want to buy, to engage to what they need and then getting that right offer or content in front of them.
Something that Netflix does very well in terms of helping us to binge watch.

This Is Personal: The Art of Delivering the Right Email at the Right Time (07:12.540)
Yeah, and that's another thing too.
Like I always bring up the Netflix example because they don't just do the recommendation engine thing, but they also go as far as to change the COVID art for films to be like, oh, I like Robert De Niro.
So if he's in a film and they show me that film, it's probably going to be him on the COVID Whereas somebody else who likes some other actor would see potentially somebody else.

Omer (07:35.740)
I did not know that.

This Is Personal: The Art of Delivering the Right Email at the Right Time (07:37.400)
Yeah, they do that.
It's wild.
We're not that behavioral science Y to be honest, a lot of the way that people use us is a lot more straightforward.
Like we basically allow people to set up flowcharts or automation campaigns as a flowchart on your site.
So you could say like, all right, if somebody's on my site and they are anonymous, I want to show them my newsletter, opt in form.
But then if they're back and they're not tagged customer, I want to show them my promo to be a customer.
And if they are a customer, I want to get them to an affiliate page or something that I have.
So usually what people are doing with us is to use us as a routing tool to show different content, whether those be popups or call to action buttons in your nav or different hero areas or whatever else depending on who you are and what you should do next.
And the benefit of us is we work as a JavaScript to include so it's not dependent on any content management system.
You don't need to use us.
You can keep using WordPress or Webflow or whatever else and that's been kind of nice and compelling for a lot of people too.

Omer (08:42.400)
Great.
Give us a sense of the size of the business.
Where are you in terms of revenue, number of customers, size of team?

This Is Personal: The Art of Delivering the Right Email at the Right Time (08:48.240)
Yeah, so we're at about 20,000 in MRR, which I'll get into more of that later as to why we're not higher.
And we have about 250 paying customers and our team right now is three and a half effectively.
So three full time and and then a part time person helping with design right now.

Omer (09:05.290)
One of the reasons I wanted to invite you onto the show was one, I think it's an interesting product, but it's a very interesting story as well where there have been a lot of ups and downs on this journey and I think that for a lot of the times I'm talking to founders who are, you know, 10, 20 million in ARR and there's useful lessons to learn there.
But a lot of people listening to the show are at much earlier stage trying to get to the first hundred K in ARR or something like that.
And I often hear from people, it's like hey, we want to hear more of the stories of people who are just ahead of us rather than building sort of an eight or nine figure business.
And with your story in particular, I think there's some really interesting lessons that hopefully we can distill down and help people listening to this kind of go away and on the one hand get some maybe motivation or inspiration if they need it and two, some ideas on when things aren't working, how do you turn things around, what do you do and some of the things that you've done over the last year to take the business that was effectively like I think you said, for a year, year and a half, almost two years, there was stagnation, there was decline, and then you turned things around and the businesses started growing again.
So I think there's some really, really helpful, useful things to unpack there.
So I'm going to try my best to make sure that we cover all those things.
Let's start with where the business was founded.
So I think it was 2017.
Where did the idea come from?

This Is Personal: The Art of Delivering the Right Email at the Right Time (10:50.890)
Yeah, so I had, at the time, I was kind of known for this course, video course on email marketing.
And one of the bonuses of this course was a zip file with a bunch of JavaScript in it that allowed people to put the JavaScript under your site, tweak it a bit, and then you could use that to change content in your website using jQuery, you know, like change different headlines or whatever else depending on data that you had in your email platform.
So I was teaching people how to do things like, oh, email marketing.
Done, done.
Right.
One component of that is to segment your list.
Oh, why don't we make it so if they're segmented by industry, maybe change up your sales page, just have, like, testimonials for that industry.
Right.
So I included some boilerplate code that they could use.
The problem was that most of the people who bought my course were people doing email marketing, and they look at a zip file full of JavaScript files and they're like, what is this?
So one of the.
One of the customers of that course was a guy named Ankara Nagpal, who at the time owned a company called Teachable.
And he's like, stop screwing around.
Can you just make this a SaaS?
And I was like, sure.
Like, that sounds great, but, you know, money, time, all that kind of stuff.
And he said, well, how about this?
I will help organize some fundraising.
You bring on somebody to work on it with you.
And yeah, let's make that happen.
So that's exactly what ended up happening.
We raised about half a million dollars in 2017 to convert a zip file of JavaScript into a functional software as a service business.

Omer (12:32.510)
Great story.
Yeah.
I found a tweet from you where you said, like, right before Write Message was Write Message, it was a bunch of custom JavaScript that managed to sync with Drip's API.
And I think it's hilarious that Ankur was like, no, that's too hard.
If I remember, he was the guy who built the first version of Teachable, wasn't he?

This Is Personal: The Art of Delivering the Right Email at the Right Time (12:54.200)
Yeah, he was the owner and founder of Teachable.

Omer (12:56.520)
Yeah.

This Is Personal: The Art of Delivering the Right Email at the Right Time (12:57.080)
Yeah.
Well, so most of our customers are the ones saying the JavaScript thing was too hard because a lot of them were, again, people who were just using Drip to send.
They weren't web developers or anything like that.
Right.
Ankur knew what it was and he's like, what if you put a hosted front end to this thing that we like and set up stripe behind it to Charge people monthly.
Like that sounds like a good plan, doesn't it?
So that's the origin story of the conversion, if you will, from a zip file to a software business.

Omer (13:31.330)
When you raised that seed round, did

This Is Personal: The Art of Delivering the Right Email at the Right Time (13:32.610)
you have any customers at that time of the course?
Yes.
No.
We raised it before we had anything for the SaaS.

Omer (13:40.650)
So why do you think you were able to raise that money?
I mean, it wasn't huge, but it's not an insignificant amount of money to raise half a million dollars.

This Is Personal: The Art of Delivering the Right Email at the Right Time (13:50.330)
Yeah, to be honest, we could have raised more, potentially.
We had offers to do more, but we thought that's what we needed.
So why.
I think it helped.
And again, this isn't to toot my own whatever thing, but I had a successful exit before.
It wasn't a huge exit, but back in 2015, I sold my first business plan, Scope.
And since then, and before then, I had.
I've always been good at the whole, like, going to conferences and networking with the right people kind of thing.
So the fundraising effort, honestly, like, I didn't have a slide deck or I'd never done any.
Anything like that.
It was really just fired off an email to Nathan Barry.
Hey, thinking of doing this un.
Rob Walling.
Hey, thinking of doing this un.
It's all people I knew, friends of mine.
So it was more of a friends and family kind of thing than me doing actual fundraising.
So I did have an advantage there, I admit.
But, yeah, I mean, the fundraising part was relatively easy.

Omer (14:51.810)
Now, I remember the first time I came across you was.
I think I heard a podcast more than 10 years ago talking about Planet Scope.
It was like, yeah, it's like we're showing our age now.
All right, so you raised this money, and what did you do in terms of, like, how long did it take to build the SaaS version of this JavaScript code that you had?
And what was the journey to getting to those first 10 customers?

This Is Personal: The Art of Delivering the Right Email at the Right Time (15:24.950)
Yeah, so what we did was we raised the money, and then I kind of went off and tried to use the money by building up a team.
Right.
So while that was happening, Shai was working on the initial kind of mvp, if you will, of the product.
And we.
I want to say we.
I think we incorporated in November of 2017, and I.
We launched in about January.
So it was about four months or whatever that is, from like, official incorporation with the money in the bank to selling something.
So what we did was I was kind of recruiting with the money, you know, using the money.
And then also we put together a very simple kind of teaser page that was effectively a 500 word sales letter that had an opt in form at the bottom.
And how we showed instead of told with this page is I wrote some custom JavaScript with some drop down fields or drop down forms where you could say dropdown of industry to whatever, dropdown of email platform, choose ConvertKit, choose Drip, choose HubSpot, whatever.
And it would change the text in real time as you did that.
And that was kind of our way of saying our tool will let you do that.
Imagine if you knew this person is this or this person is that.
They're looking at a sales page or a webpage or whatever and this is what would happen.
Obviously it wouldn't be as overt, but this is effectively what would happen.
So we actually built up an email list of a few thousand people.
I think it was at about three or four thousand people by the time we launched with that.
And I kind of also, while doing that, got invited to speak at a few different events and I couldn't point people to sign up for a product.
So I just said, hey, go over here and you know, drop your email address.
And then I just kept emailing it once a week and kind of built a newsletter, you know, around this kind of idea of personalized marketing.
And it was nice because by the time we launched in, I think it was January or February of 2018, we actually hit like 10,000 in MRR pretty much within a month, I want to say.
And we did that by.
Because my background alongside PlanScope was selling like courses.
I used to have a company called W Freelancing where I sold a bunch of courses on freelancing and stuff.
So I kind of treated the launch of the product like I would launch a course.
So there was urgency, there was like a, you know, a pricing scheme that if you bought launch week you'd get a good deal and stuff like that.
So we actually had a nice like burst of momentum.
You know, we had this new team being developed and we actually were growing really nicely and like 20% month over month.
And I want to say about a year into it we were pretty much at about 35,000 in MRR, which I was really happy about.
But then reality started setting in and I realized I couldn't just keep doing the whole digital product launch strategy stuff for software business and the whole audience thing could only go too far.
And a lot of what ended up happening was we realized, okay, the tool we built, people, people were wanting it because it's cool, it seemed interesting, but we didn't really have a Lot of case study data to back it up with at the time.
And on top of that, the only way to personalize your website is if you have the segment data, like what industry someone's in.
And a lot of our customers were like, how do I get that information?
Right?
Like, you know, we're kind of like, you know, if this, then that and we're that, then that.
But they didn't have the if this bit.
So we were like, oh, you know, we kind of had this, I don't know, this kind of issue where our rocket ship was starting to kind of falter.
And yeah, from there we, you know, a little after that we quickly had ran out of that money.
Never got that continuous 20% month over month that would have made it.
So we didn't, you know, run out of money.
And we kind of reverted back to effectively being a operationally a bootstrap team with myself and my co founder.
And we were living off the money we had and we kind of pivoted the product to then also allow for segmentation so we could satisfy the if this part.
But it wasn't just growing the way we wanted it to and we were struggling.
We were kind of lost in the wilderness for a bit.
And then we both kind of got demotivated and we didn't go separate ways and we, we were still tending to the product, at least the support system and stuff like that.
But there wasn't no forward momentum on the product.
There wasn't momentum on the growth side or the development side or anything like that for years.
And we just kind of like we shot up and then we kind of petered down over time.

Omer (20:08.370)
Okay, great.
So let's kind of talk a little bit about that.
So first of all, the getting to the first 10k in MRR and then getting to around 35k happened fairly quickly.
But in many ways you had been working on this for much longer than that because you had been building credibility and authority in the email marketing space.
You had already been building an audience before you had been building this email list.
So I think a lot of the times we discount that.
But there's a lot of pre work that went into laying the foundation, having this audience in place before you were able to get those types of results.
So you raised the 500k seed round around 2017.
Initially, things are looking good, revenue is growing.
Your, you're inching your way towards what, half a million in ARR.
And then you start to run across some of these issues.
You'd already hired a team and so you have effectively a burn rate to worry about.
And then is that basically that thing that happened?
You just got to the point where it was just like, okay, we've got this money coming in, but we're spending more then we're bringing in.
We have gone through the money that we've raised.
We can't afford to keep this team around anymore.

This Is Personal: The Art of Delivering the Right Email at the Right Time (21:41.660)
That's exactly what happened.
Yeah, we were making some money, but our burn was higher.
And we always thought before, it's that quintessential kind of founder thing of before we run out of money, our revenue will grow such that it surpasses our burn.
And that didn't happen.
And I think we hired fast because we thought, why have half a million dollars in the bank, might as well use it.
So, yeah, I mean, we were kind of a victim of our own success in a way, or at least early success.
And yeah, we just realized, okay, so we kind of gradually pared back the team and then we just had to realize, okay, like.
Like both for Shai and myself, we wanted to take out a livable salary.
I mean, he was in North London.
I was at the time in the U.S. we've got families and stuff.
Like, we can't do the ramen thing.
So for that to happen, that meant once we dropped below about 20,000 in MRR, so we were gradually declining because a lot of that early growth was people getting a great deal, but then no one's going to keep paying monthly if they don't act on that deal.
Right.
So we didn't have the software at the time to really make it.
So a lot of people could really benefit from the product because they didn't have the segment data.
So when we got under 20k, it's like, okay, that's when again, we're now just after product expenses, like the server and everything else and all the stuff.
Divide that by two.
And that's pretty much what shape Shai and I would need.
So that's around when we were like, okay, we just need to go back to just you and I live off this.
Hopefully we can keep it steady and even if we don't make any more anytime soon, at least we're able to live off this.
But yeah, then we both.
I think it was just the lack of growth we were seeing and everything else and not really sure what we had to do next.
It just.
We both got very demotivated and yeah, we just kind of like stagnated again for a while.
And I pursued other things.
He pursued other things.
Product was still there.
We had a core group of customers who were still benefiting from it and loved it, but we weren't doing much on the growth side.

Omer (24:01.150)
So you effectively keeping the lights on, you're making sure that you're providing support for the customers that you have, but you're not actively trying to go out and figure out, you know, investing in marketing or sales and growing the business or I guess, evolving the product.
And this was that period that went over for about, I think you said, like a year and a half, two years.
What changed then?
Because that's a long time to go through feeling unexcited about a product and a business.
And yet when, you know, we talk about what you're doing now, I sense energy, enthusiasm.
What made the shift?
What got you excited again?
What got you believing in this thing again?
Because, man, I know if I'm like.
If I personally, like, I'm down about something and I'm ruminating for, like, three days about feels like forever just to turn myself around from that.
Right.
Maybe it's just the way my brain works, but to kind of go through that for years and then turn things around and get excited and find a reason to put your heart, your soul and energy back into this.
What was that process like?

This Is Personal: The Art of Delivering the Right Email at the Right Time (25:21.250)
Okay, so I think the way I'd describe it, if you will, is that last year, so 2023, we kind of had this Hail Mary attempt to reinvigorate things, and that was to do the thing that is usually always a horrible idea, but we did it anyway, which is, let's start a new code base and dramatically simplify things and have it.
The product, instead of it being a platform, which it is, just make it do one thing and do one thing really well and sell that.
So we did this, and now we kind of ran this horrible issue where we had, like, two code bases to support all this stuff.
It just.
It didn't.
Again, that what?
That didn't work, right?
It didn't work the way we wanted it to.
And at that point, we were both like, okay, this.
We need to either, like, just shut things down and kind of effectively screw over the customers, you know, and at the time, we had, what, 150, 200 customers who were using us, and they kept paying.
So presumably they liked using us and were getting benefit from the product.
We shut it down.
We sell it.
Which selling a declining asset doesn't work usually that well, or one of us buys out the other.
I didn't want to sell it because my last time I sold a business plan Scope, the new owner drove it in the ground and it hurt me reputationally because I was so tied to that product.
I didn't want to shut it down because again, I knew a lot of these.
You know, the customers I mentioned, these were like people I knew from my other.
Because I've got other income sources besides Direct Message.
I sell courses and I've got like a book and all this other stuff.
These were kind of the.
A lot of the fanboys, if you will, of my stuff.
And I didn't want to screw them over.
So the only option was either he buys me out and tries to like make it better, or I buy him out.
He didn't want to buy me out and I was really wanting to buy him out.
So that's the direction we went.
And so, yeah, I ended up basically cashing in a lot of my savings things personally to buy out his equity, which again, as a declining asset, it meant just like if we were sold on the open market, I got what I think was a good deal.
And then, yeah, so I was like, okay, I bought this thing with my own cash, so what do I do with it?
And the big change that happened, I think, was the realization, and you and I talked about this kind of briefly earlier, before we hit record, was that what if, like, we were getting rejected because people saw our.
Our thing is too confusing.
And I knew we have an onboarding issue, we have like a product UX issue, we have all these issues.
So I thought, okay, what if I just go to people who I would love to be a kind of a flagship Right Message customer and say, hey, pay me to consult.
You don't even need to use Right Message.
Or you pay for Right Message and you pay for my consulting fee.
And I will use this tool that for a lot of new people is kind of confusing on your behalf and make it work really well the way it's supposed to.
So I did that and I did that again and again and again.
And that's been brilliant because we've now have some of the biggest named creators on the Internet using Right Message.
And on their website, under our widgets it says powered by Right Message.
And we have all these people now.
We get people all the time because they sign up and we ask them about, like, how do you know about us?
And they're like, oh, Justin Welsh or Matt Gray or Dan Go or Ben Meir or something.
And it's these people with hundreds of thousands of people on their email list who make millions a year in sales.
They're all now these great advocates of ours, because they're using us.
So that to me has been the biggest.
I'm using that momentum to say, okay, now I can use this money and this momentum to make it so it is self serve, a really good experience for self serve customers.
Because I don't want to be doing, I don't want to do like if you remember Bounce Exchange, their model where they had opt in software that the only way to use their opt in software was to hire the agency to do the copywriting and the design work for their internal tool.
I didn't want it to be this weird services company that happened to have intellectual property under the hood.
I wanted us always to be a proper, you go to the website, you sign up for a trial, you buy it kind of thing.
But I think this momentum over the summer that started and the case studies we're getting now, like we just.
For Justin Welsh, we helped him increase overall conversions for his course launch by 38%, which was hundreds of thousands of dollars now attributable to our software.
And now we're like, we need to just shout this everywhere.
And really.
So that's been the big inflection point I think for us is I think my co founder and I, when we started, we did the kind of quintessential, we don't want to talk to people, go to the website if you want to talk to us.
We have a support email address.
But I was much more willing now that I had my own money behind it to say like, I'm happy to sit on demos all day and just grind it out to sell people just so I don't look like an idiot in front of my wife and being like, hey, I blew our retirement on buying this like failing thing that I had started.

Omer (30:42.470)
So you went from a software as a service to software and a service,

This Is Personal: The Art of Delivering the Right Email at the Right Time (30:47.670)
but it's still not that.
I mean, you can still buy it independently, but.

Omer (30:50.270)
Yeah, right, right.
This was basically a way for you to.
It's basically a growth strategy and it helps you raise some additional money to fund the business.
And you were telling me earlier that it's basically the same playbook that Nathan Barry used with ConvertKit.
And did he kind of, you know him, did he kind of help you kind of with this or was that something that you had just seen?

This Is Personal: The Art of Delivering the Right Email at the Right Time (31:20.100)
I've known Nathan for years.
I mean, he's an investor in Right Message and he and I used to teach joint workshops and stuff before.
I remember getting a call one day from him saying, hey, I'm thinking of starting an email platform.
I was the first person to help him hire, I think, one of his freelancers by vetting their GitHub account.
So, like, he and I go way back and I remember seeing how he struggled a lot early on with ConvertKit.
Like, I mean, now it's doing what, like 2 million a month or whatever it is?
Or 3?
It's doing great now.
But when you look at the, like, it was floundering at a few thousand a month for a while.
And the big inflection point for him was he didn't partner up officially, but he got in terms of equity, as far as I know.
But Pat Flynn of Smart Passive income basically championed ConvertKit to his email list and got all the wannabe Pat Flynns to start using ConvertKit.
So that's exactly kind of the playbook I'm using, because what they did after that is then Nathan went to every peer of Pat Flynn and said, hey, Pat's using ConvertKit, you should too.
And then he did the same with the fitness space and the food blogger space and all this stuff.
And that's kind of what we're doing now is we're like a lot of the biggest players in the kind of pro space creator space are now using us.
And now I can confidently say, like can name drop these people and say they all trust us and we're helping them make meaningful amounts of money.
Here are some examples and case studies of it, and I think that's going to be ultimately our saving grace.

Omer (32:57.610)
So who was the first?
Let me say that carefully.
Pro space creator, one word that you signed on, who was that and how did you go about getting that deal done?
Because I've seen a lot of people try to do these things and fail miserably at it.
So what did you do differently?

This Is Personal: The Art of Delivering the Right Email at the Right Time (33:17.760)
Funny enough, it was Pat Flynn and I knew him again, I mentioned conferences earlier because he and I played craps at a table in Vegas at the after party of or after a conference we were both at.
So I think I've really tried hard to build up really good professional relationships.
I'm friendships, I say professional, but these are all people I text and all that stuff.
So these are people that I genuinely like as people.
And yeah, I think he was the first one.
And the more recent ones, like I've named Justin Welsh and Matt Gray and everyone else, those are all since the summer of 2023, so they're all kind of recent as of our recording.

Omer (34:05.130)
So Pat was the first one, I think.
I don't know Pat.
I'VE known about him for many, many years.
But to me, he just seems like a genuinely nice guy.
There was a time back, I remember I went down to San Diego and I was thinking about.
We were actually thinking about moving there at one point, and I thought, who do I know in San Diego that could tell me about where to, you know, it's kind of good places for families to kind of move to and stuff.
And I didn't know anybody.
I thought, well, Pat Flynn kind of knows about San Diego, right?
So, so just randomly, I just sent this email to him because I used to listen to his podcasts and stuff and, and I'll never forget he actually replied and he listed out a bunch of communities and places to go and see and stuff.
And it was like he didn't know me from, from Adam.
And, you know, he took the time to do that.
So I think he's.
It just kind of just, you know, show me.
He really is a very genuine guy.
So I'm glad that he was also there.

This Is Personal: The Art of Delivering the Right Email at the Right Time (35:05.140)
Well, their whole team, like, there's so many great people spi.
I mean, obviously the face of it is Pat, but yeah, I mean, Matt Garland, who's, I think, the CEO now.
Ish.
I want to say, like, I think Pat lately has been like, more he's not managing the team as much.
And Matt's been doing that.
Matt's a great friend too.
I mean, they've got like, yeah, they've got it all put together well.
So good company, good brand.

Omer (35:32.570)
And then so going to Justin, Justin Walsh, was that just off the back of just saying, hey, you know, we've, we've been working with Pat or no.

This Is Personal: The Art of Delivering the Right Email at the Right Time (35:41.130)
So I think one of the things that really has helped a lot is I have a course.
You know that that earlier course used to be called Mastering Drip.
I now have Mastering Convertkit.
Right.
And that's something I've had for years.
And I got a DM from, from.
From Justin once, I want to say, like last spring or something, where he was like, hey, I've heard good things about your course.
I'm looking at the sales page.
I don't have time to go through a course.
Can I just pay you?
And it pretty much boiled down to that.
And I think that's one of the things is like the course and the email marketing training for me, nicely and perfectly compliments, like, it provides the why behind the how.
Right.
So I kind of look at it as like if the software is the pickaxe, the training is the map of where to go and Swing the pickaxe.
Right.
So I actually have found that that's something we haven't really talked about yet.
But that's been a huge kind of component, I think of all of this has been like, I'm about to release a new course on segmentation which I'm teaching how to do it with Write Message, or you could do it with Typeform, or you could do it with Tally, but obviously with Write Message I want you to use that.
Oh, and by the way, if you buy the course, you get a credit equal to what you paid for the course for Right Message.
So there's a lot of, I think there's a lot of room for not just going like for me, if I'm just selling website personalization or segmentation software, you need somebody who already knows that they need that before they're willing to even, you know, commit to your product.
Whereas if I do something that's more training, where it's like, hey, here's how to better think about better understanding your audience, what that means, what you could do with this, so on and so forth, and it's a video course, then that's kind of the gateway drug into Right Message for me.
So my like whole grand plan for marketing is not going to be doing like the traditional SaaS marketing stuff.
It's going to instead be how do I build a lot of great training stuff and have these great big case studies that can push in the training is examples and teach it and all that kind of stuff and have all roads lead to Right Message.
And that's basically my plan for the year when it comes to growth.

Omer (37:48.980)
So you've got basically these pro creators that you're working with is helping you build the credibility.
You're getting case studies from those so people can now not just see the functionality of Right Message, they can actually see it in practice.
Having powered by Right Message on these people's websites probably doesn't hurt either in terms of getting leads.
Is there anything else that you're doing or is it just that one thing that you're focusing on and just doubling down on that?

This Is Personal: The Art of Delivering the Right Email at the Right Time (38:24.820)
It's pretty much it.
We're not doing any paid ads.
We regrettably haven't touched our blog in a over a year, which I think is a big issue because I think a lot of people gauge is this thing still around by when the last blog post was?
So I am planning on fixing that, but it's really been a matter of bandwidth, honestly.
And that's why a lot of like you said earlier, the Consulting revenue I'm using as a secondary fundraising tool to hire people who can help with that kind of stuff and make it so we can have fresh blog content and everything.

Omer (38:54.350)
It sort of reminds me of the way that you're positioning the course and then offering the subscription behind that.
It reminded me of what Russell Brunson did with ClickFunnels.

This Is Personal: The Art of Delivering the Right Email at the Right Time (39:10.440)
I was just gonna say.
I thought you might say that.
Yeah.

Omer (39:12.839)
Was that an inspiration for you?

This Is Personal: The Art of Delivering the Right Email at the Right Time (39:14.280)
Not really because I've.
I've honestly never gone through Russell stuff.
I obviously know who he is, but I've never bought his book.
I've never.
I don't even know what his.
How clickfunnels.
I know conceptually what it is, but I've never used it.
But yeah, I mean, there's probably a degree of that.
I've always, weirdly enough, even though I'm in kind of the email marketing space, I've never tried to identify as an Internet marketer.
So I've kind of shied away in a weird way from the stuff Russell's doing.
But yeah, I think there's probably a lot of overlap because that was.
His playbook is like, you know, teach the.com secrets or whatever his book was called.
And.
Oh, and by the way, there's ClickFunnels.

Omer (39:55.850)
Yeah, yeah, no, I think that was.
I think that's brilliant because, you know, Everybody goes into SaaS and everybody thinks that there's one way to sell software.
And, you know, he came along and said, actually I'm gonna sell an info product.
And on the back of that, a SaaS product.
And again, what is it, 100 million whatever plus business.
There's different ways to.

This Is Personal: The Art of Delivering the Right Email at the Right Time (40:21.200)
I mean, even with ConvertKit, Nathan had written a book called Authority, which a lot of the early ConvertKit customers came from that.
So I think it does make sense.
I mean, it's not maybe for every SaaS, but if you've got like the issue with write messages.
We're one of the few software products that do what we do that are not in the enterprise space.
So, you know, like our competitors are optimizedly and stuff, which again, we're not going after optimizely type customers.
So it's been a little weird thing.
We've had to really educate people in order to make a case for our product.

Omer (41:02.320)
When I first came across right message, it sort of seemed to be targeting like SaaS companies.
So at least that's the impression that I got.
And that's not surprising where you get a lot of products and they say, well, we'll go after SaaS companies to start with because why not, right?
Just maybe help us understand why you didn't go down that path, why you chose these creators as your target market.
What I'm trying to just understand is like, how did you figure out what that niche was, what that target market was and where you could differentiate yourselves?
And did you stay away from SaaS because the product didn't really work there or because you realized it's going to be much harder for us or for me now to clearly position this as a differentiated or unique enough offering that would get their attention?

This Is Personal: The Art of Delivering the Right Email at the Right Time (42:03.480)
Yeah.
So early on and even to agree to this day, we tried to cast a wide net.
So we mistakenly thought, okay, anyone who does email marketing should use right message.
That meant SaaS, it meant E commerce, it meant, you know, plumbing companies, it meant creators or whatever.
They weren't even called creators when we started, but that's the new name for them.
And the, Yeah, I think the reason the creator thing has worked well for us has been with SaaS.
Typically, usually the extent of email marketing that they do is like product update emails.
Right.
Like a lot of them aren't really doing a lot with thinking, okay, I need to have like nurturing sequences and I need to have like a weekly newsletter and I need to like think about audience building and like this kind of thing of like, you know, sending people from the email to the website back and forth and back and forth.
Whereas creators do think like that, especially the ones we're going after that, you know, they're thinking, okay, I've got a portfolio of courses or high end coaching offerings and yeah, if I could just, you know, uncover a bit about somebody's psychographics, like why are they here, what are they struggling with?
I can change the way I pitch my thing next time to speak more directly to them.
And I think that makes a lot of sense to the kind of people we're going after now.
And equally, I think that also works with E commerce.
I just don't know anything about that world.
And I think that's actually a good thing because there have been some kind of right message kind of companies, but they're all targeting E commerce now.
So I'm like, okay, fine, keep them there.
Right.
And also to kind of close that out, I'm a creator myself.
I mentioned I've sold well over 5 million in digital courses since 2011, or however long I've been doing.
It started out as ebooks, then shifted to video courses.
I've run conferences before.
I've done the whole, or used to call info product business.
That has now shifted to creator business.
I've done that and I still do that.
I kind of, I think, know that audience.
Even though I'm a SaaS founder myself, I'm more aligned, I think, with creators than other software businesses.

Omer (44:26.830)
And I think in many ways that's a really important factor.
Like when I talk to a lot of founders who are sort of early stages and they're trying to figure out what their target market should be.
And often the factors that they'll look at is the usual stuff in terms of do they have the problem, is the market growing, all of these things.
Can I reach target?
Can I reach these people?
But then the question I always ask is, do you actually like working with these people?
Do you want to spend the next 10 years of your life working with these people?
And sometimes, really the answer is like, no, I don't.
And so it's like, okay, well, find someone.
Find somewhere else.

This Is Personal: The Art of Delivering the Right Email at the Right Time (45:09.680)
That's why I didn't go after Enterprise.
I dabbled with Enterprise accidentally.
We had a big Fortune 500 who somehow found us.
They reached out and I spent probably at least 20 hours on calls with like, teams and this and that, like all these people.
And it never turned into anything.
And they just wanted to do meetings all day.
And I'm like, I just don't like if that's granted.
Yes, maybe you hire that out, sure.
But I didn't want us like at our.
In our DNA.
I always liked.
I know this is kind of the often cited example, but I liked always what Basecamp.
What they used to say about, like, Microsoft can come and sign up for Basecamp.
The max they're paying is 99amonth.
They can't make us change our code base.
They can't keep us, you know, up at on Saturday building some custom feature that they need.
Whereas when you have like a, you know, an enterprise company paying you a ton of money, that's kind of what they expect.

Omer (46:04.810)
Yeah.
All right, we should wrap up.
So let's get on to the lightning round.
Got seven quick fire questions for you.
Just try to answer them as quickly as you can.
What's one of the best pieces of business advice you've received?

This Is Personal: The Art of Delivering the Right Email at the Right Time (46:16.890)
I think for me specifically right now, it's play up your strengths.
Because I think, like a lot of founders, I always want to appear bigger than I am.
And I've come to embrace, like, hopping into my Help Scout inbox and sending a thing to a customer where in the signature, it's Like Brennan Dunn, founder comma right message and people being like, wow, this is from the guy who owns it.
And it's actually not just a scripted outsourced support thing.
So I think play up to the strengths that you are small and can do things that the bigger players can't do.
It's good advice I'm trying to live by.

Omer (46:54.180)
What book would you recommend to our audience and why?

This Is Personal: The Art of Delivering the Right Email at the Right Time (46:56.500)
So my favorite business book is a book called Badass Badass.
The subtitles making Users awesome.
It's by Kathy Sierra, who is probably like she hasn't really.
She's kind of been hidden for the last few years.
But it's the best book I've written on usability and ux, so highly recommended for everyone.

Omer (47:20.070)
What's one attribute or characteristic in your mind of a successful founder?

This Is Personal: The Art of Delivering the Right Email at the Right Time (47:23.990)
Focus.

Omer (47:24.710)
What's your favorite personal productivity tool or habit?

This Is Personal: The Art of Delivering the Right Email at the Right Time (47:27.590)
Having kids, they force me to work in a very constrained manner, which makes me very productive.

Omer (47:36.310)
What's a new crazy business idea you'd love to pursue if you had the extra time?

This Is Personal: The Art of Delivering the Right Email at the Right Time (47:39.350)
I'd love to build a really good email marketing platform because I have nitpicks with all the existing ones.

Omer (47:45.680)
What's an interesting or fun fact about you that most people don't know?

This Is Personal: The Art of Delivering the Right Email at the Right Time (47:48.640)
I have my pilot's license.

Omer (47:50.240)
You do?
Wow.

This Is Personal: The Art of Delivering the Right Email at the Right Time (47:51.280)
I do.
Yeah.

Omer (47:52.800)
And finally, what's one of your most important passions outside of work?

This Is Personal: The Art of Delivering the Right Email at the Right Time (47:56.160)
Kind of boring now that I've got a two year old, but I do when the weather's nice as we were talking about earlier.
When the weather's nice here in England, I love cycling in the English countryside.
I love just road biking and going through random villages and nice pub lunch at a 400-year-old pub or something like that.

Omer (48:16.360)
Yeah, we were just for people listening, like you and I were talking about how you're the American who's now in England and I'm the British guy who's now here in the us Although I'm American now as well, so I have to play up both sides of the Atlantic now.
So that's great.
So thank you so much for joining me, Brendan.
It's been a pleasure to finally chat and share the story of Right message.
Looking forward to seeing what you continue to do over the rest of 2024 as you're getting more and more momentum with this business and now basically kind of setting out on the new chapter as a solo founder effectively of the business this time.
Also, we should talk about you published a book last not that long ago.
I think it was about five, six months ago.
Right.
Which is called this is Personal the Art of Delivering the Right Email at the Right Time.
And I was thinking at some point like maybe we should get you back and just pick your brain and maybe just educate people about some of the things you teach in that book.
Because there are some really good best practices about email marketing that everyone should be implementing and is not implementing today.
And I won't mention any names but me.
And then also the course that you mentioned.
So that's called Mastering convertkit and I think the website is what createandsell Co.

This Is Personal: The Art of Delivering the Right Email at the Right Time (49:54.170)
Yeah, Create and Sell is like my digital products side of my world.
It's a weekly newsletter and it's also courses.

Omer (50:00.720)
Yeah.
Cool.
So if people are interested in that, you can go and check it out over there.
Great.
Well, thank you so much.
It's been a pleasure and enjoy your evening in England and I wish you the best of success with.
Right message.

This Is Personal: The Art of Delivering the Right Email at the Right Time (50:14.400)
Thanks so much for having me, Omer.

Omer (50:15.920)
My pleasure.
Cheers.

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Ulf Arnetz, Howwe Technologies

From 60% Churn to Zero - How Howwe Fixed SaaS Retention

Ulf Arnetz is the co-founder and chairman of Howwe, a SaaS product that helps enterprises to accelerate strategy execution and financial results. In 2019, after running a successful services company for several years, Ulf made the decision to transition it into a SaaS business model. He and his team had been working on a SaaS product for a while. They believed there was a huge growth opportunity and felt ready to make the switch to SaaS. But the path to becoming a fully-fledged SaaS business was far from easy. Their annual revenue dropped considerably, going from $5 million to just around $2 million. While Ulf had prepared for a short-term drop in earnings, this turned out to be more substantial than he had expected. Selling their SaaS product to CEOs was also another big challenge. Although they eventually found a solution, they also realized that they were often losing deals because they hadn't figured out how to deal with other key execs who were resistant to using the product. And probably one of their biggest challenges was grappling with a jaw-dropping 60% churn rate. Their SaaS product just wasn't up to par and triggered widespread employee dissatisfaction. Despite those struggles, Ulf and his team persisted and eventually found product-market fit.

How $6K in SEM Launched an Enterprise Sales Machine - Vineet Jain

Vineet Jain, Egnyte

How $6K in SEM Launched an Enterprise Sales Machine

Vineet Jain is the co-founder and CEO of Egnyte, a content collaboration and security platform for mid-market and enterprise businesses. Vineet arrived in the US with $100 and no connections. He spent four and a half years at KPMG learning to sell to everyone from line managers to CEOs. That convinced him he could build something of his own. In 2001, right after the dot-com bubble burst, he co-founded Valdero, a supply chain software company, and raised $7.5 million from Kleiner Perkins. Revenue grew quickly. Then Oracle and SAP moved in. Pricing pressure crushed them. They sold. Investors made money. The 70 employees didn't. That failure stuck with him. In 2007, Vineet and three co-founders rented a small office. No funding. Two did consulting while the other two wrote code. The idea: move the physical file server to the cloud. When they launched, analysts lumped Egnyte in with Box and Dropbox - hundreds of companies chasing the same market. Everyone told Vineet to do freemium. His board pushed back. Analysts questioned how they were different. Vineet Jain built Egnyte to over $300 million in enterprise sales revenue using three strategies: charge from day one, offer hybrid cloud when everyone said go cloud-only, and keep cost of acquisition low with inside sales offices in cities like Spokane and Raleigh instead of Silicon Valley. In 2016, Gartner named Egnyte a leader - a tiny company standing alongside competitors that had raised billions. Today, Egnyte has 23,000 customers, 1,400 employees, and has raised just $137.5 million with no additional funding since 2018.

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