30 Years, 5 Exits: How Serial Founder Russ Fradin Pivoted Dynamic Signal From Influencer Marketing to $50M ARR

Most founders get one shot at building a company. Maybe two if they're lucky.

Russ Fradin has been founding, exiting, and reinventing companies for thirty straight years—from Flycast Communications in 1996 through his current venture, Larridin, which raised $17 million in seed funding led by Andreessen Horowitz in 2024.

His most instructive journey? Dynamic Signal. Founded in 2010 with co-founders Steve Heyman and Jim Larrison, the company started as an influencer marketing platform for bloggers. After eighteen months and $5-6 million in ARR, Russ realized something critical: customers were happy, paying well, but the business fundamentally wasn't sticky.

So he walked away from it. Completely.

He went to investors in 2014 and said: "I know I have $4-5 million in ARR. Completely ignore that. I'm walking away from it. This $200,000 in pipeline—that's what you're investing in."

That decision led to building what became a $50 million ARR enterprise communications platform serving 35 million employee seats across 600 Fortune 2000 companies before being acquired by private equity in 2020.

Key Takeaways

• Russ Fradin, Steve Heyman, and Jim Larrison founded Dynamic Signal in November 2010 after previously working together at Adify, an advertising infrastructure company
• The original influencer marketing product reached $5-6 million ARR but wasn't sticky—customers treated it like media buys, not recurring software
• Emergent behavior from employees (not traditional influencers) sharing company content revealed the real opportunity
• Dynamic Signal reached approximately $50 million ARR before being acquired around 2020
• Dynamic Signal merged with SocialChorus in 2021 to form Firstup
• Russ raised $17 million for Larridin, an AI measurement platform, led by Andreessen Horowitz with contributions from Gradient, Bloomberg, Haystack, and Homebrew
• After just 20 employees and four sellers, Larridin has tens of customers selling AI productivity measurement to CIOs and CFOs

Table of Contents

1. The 30-Year Journey: From Flycast to Larridin
2. Dynamic Signal's Origin: Influencer Marketing for Bloggers
3. The $5M ARR Problem: When Success Isn't Really Success
4. The Pivot Nobody Saw Coming: Employees as Influencers
5. Building the Employee Communications Platform
6. When to Walk Away From Revenue
7. Selling to 600 Fortune 2000 Companies
8. The Carbon Health Interlude
9. Starting Larridin: AI Measurement in the Enterprise
10. Lessons From 30 Years of Finding Product-Market Fit

The 30-Year Journey: From Flycast to Larridin

Russ Fradin joined his first Silicon Valley startup in the mid-1990s, before Netscape had even gone public. He was one of the first employees at Flycast Communications, the first online advertising network, which went public and was eventually sold for billions in the late 90s.

From there, he became one of the first executives at Comscore, helping build the internet measurement company before it had revenue. He spent a year trying (and failing) to fix wine.com—"not a great business, but it was a fun year."

Then in 2005, he started Adify, an advertising technology company that got "very big very quickly" and sold to Cox Enterprises in 2008.

Each experience taught him something different about what works and what doesn't in enterprise software, measurement businesses, and go-to-market strategy.

But it was his next company, Dynamic Signal, that would teach him the hardest lesson about product-market fit: sometimes you have to walk away from millions in revenue to find what actually works.

Dynamic Signal's Origin: Influencer Marketing for Bloggers

Dynamic Signal was founded in November 2010, in the early days of social media when blogs were still a huge deal and Twitter was just gaining traction.

Having built a large advertising technology company (Adify) that created networks at scale, Russ and his co-founders thought there would be a similar opportunity in influencer marketing.

But influencer marketing in 2010 looked very different than today. There was no Instagram. No TikTok. Video creators weren't yet a thing.

"It was mostly long tail bloggers, pre-Twitter, pre-Instagram," Russ explained. "The way you were expressing your opinion online was really message boards and blogs."

The idea was to bundle three things together:

1. Find and identify influencers brands should work with
2. Technology to allow brands to work with them, track what they were doing
3. Backend payment systems to actually pay thousands of influencers across multiple currencies and send 1099s

"It's one thing to say we're going to work with four thousand influencers to do this thing, but actually you have to find them, identify them, contact them, make sure they're doing what they said they would do, make sure they provide the right disclosures so everything is legal. Then you actually have to pay them," Russ said.

They raised $8 million in early 2011 from 30 investors and got to work.

The $5M ARR Problem: When Success Isn't Really Success

By eighteen months in, Dynamic Signal had signed a bunch of customers paying significant money. Revenue hit probably $5-6 million ARR—"multiple single-digit millions," as Russ put it.

One early customer was a movie studio (he thinks Lionsgate) that used Dynamic Signal to launch "Abraham Lincoln Vampire Hunter"—"a good book, bad movie."

The studio was happy with the results. The campaign worked. But then the movie launched, and that was it.

"If you then became core infrastructure for Lionsgate to use to launch every movie, you'd have a very nice software business," Russ reflected. "If you have to sell it title by title, really you're just a different form of a media company. That wasn't what we set out to build."

The pattern repeated across customers:

• Campaigns would run
• Results were good
• Customers were satisfied
• But they treated it like any other media buy—not recurring software

"What we found was the customers—yes, they would run the program, the program would be interesting, they'd be happy with the results. But they treated it just like any other medium buy," Russ said.

Influencers were also getting harder to recruit. Bloggers were moving to Twitter, and recruiting "some random Twitter account" wasn't worth the effort. The software only worked at scale—if Budweiser wanted to work with three or four influencers, they didn't need software. They could just have their agency call them directly.

It wasn't that the idea was bad. It just wasn't a software company. It was a software-enabled agency services company.

The Pivot Nobody Saw Coming: Employees as Influencers

While struggling to recruit and retain influencers, Russ noticed something strange: one group consistently joined their communities and shared content without constant replacement or refreshing.

Employees.

Employees of Oakley, Lionsgate, Home Depot—they would join these communities of brand content and willingly share it. No chasing required.

"It wasn't the plan. We noticed that. It was emergent behavior," Russ said.

They started talking to customers about it. Started pitching it to prospects. And it became clear there was a massive opportunity around how companies communicated with employees.

This was the early days of social media when suddenly employees could share things about their companies publicly, but nobody knew what was allowed.

"Pre-social media, if you were the Wall Street Journal and you wanted to hear from Oracle, there were four people authorized to speak on behalf of Oracle," Russ explained. "Suddenly Twitter comes around and there's thirty thousand people."

If you're a salesperson at Oracle and want to share something on LinkedIn about your company, you don't want to get fired. You're not sure what you're allowed to say.

For B2B companies especially, LinkedIn was becoming critical for sales. But salespeople in their mid-40s had spent entire careers never talking publicly about their companies. Now they were being told "use LinkedIn more, you'll sell more"—but with no guardrails.

Dynamic Signal saw the opportunity: give employees content they're certainly allowed to share, make it convenient (mobile), ensure compliance (you won't get fired), and give credit (tracking and rewards).

The four C's: Content, Convenience, Compliance, Credit.

Building the Employee Communications Platform

The employee advocacy piece became the initial wedge. But as Dynamic Signal grew, they discovered an even bigger problem: half of American workers don't have work email.

Walmart's two million employees don't have walmart.com addresses. UPS's three hundred thousand drivers don't have UPS emails. Yet every single one has a smartphone they use for banking, dating, and everything else.

"Why don't we send people their schedule, their pay stubs, emergency announcements, live stream video of Jamie Dimon visiting a branch—all of that?" Russ asked.

The business evolved. When Dynamic Signal was eventually sold, probably 80% of content was internal-focused (schedules, pay stubs, company news), with only 20% being the external sharing that started the company.

They built what Russ calls "almost a mobile personalized intranet for increasingly disconnected workers."

By the time of the acquisition, Dynamic Signal served hundreds of enterprise organizations, including more than 20 percent of the Fortune 100, with customers like IBM, Edelman, Capital One, Salesforce, Autodesk, Deloitte, and Humana.

When to Walk Away From Revenue

The hardest decision came in 2014 when Russ went to raise a new round.

He had $4-5 million ARR from the influencer marketing business. Customers were paying. The product worked. But he knew it wasn't going to become the recurring software business he wanted to build.

So he made an extraordinary pitch to investors: "I know I have $4 or $5 million ARR. Completely ignore that. I'm walking away from that. It's this $200,000 in pipeline [from employee communications]—that's what you're investing in."

This is the opposite of what most founders do. Most founders cling to any revenue, any customer validation, anything that shows traction.

"One of the problems you have when you're a first-time founder is you don't know anybody, nobody likes you. You just have to work in your own little isolation tent and hope it works out," Russ explained.

"One of the problems you have when you're a multiple time founder is people have positive associations with you. They know the thing they bought from you last time was valuable. So actually, everybody likes your idea."

This creates its own challenge: happy ears. People tell you what sounds good sounds good. But you don't actually know if you have something until people give you money for it.

"It's very easy to have a false peak," Russ warned. "Dynamic Signal succeeded too early, too easily, because of our success at Adify. If we had been first-time founders, we would have saved ourselves a few years. Because it took us a couple years before we realized, oh, we've mostly been selling this stuff because we're just good at selling. It's actually not that great a software idea."

That's why walking away from the influencer marketing revenue—despite it working—was essential.

Selling to 600 Fortune 2000 Companies

The repositioned Dynamic Signal found real product-market fit.

By the time Russ and his co-founders were no longer involved, the company had sold approximately 35 million seats of software to 600 Fortune 2000 companies.

The business reached approximately $50 million ARR before being acquired.

In January 2020, Dynamic Signal appointed Eric Brown as CEO. Brown had previously served as EVP of CallidusCloud, where he helped deliver a 25x increase in value culminating in the company's $2.5 billion acquisition by SAP.

Dynamic Signal merged with SocialChorus in 2021 to form Firstup, creating a larger employee communications platform.

The key to their success? They never had a real churn problem.

"When I left, we had many customers that had been around seven, eight years—the entire history of the idea," Russ said. "It was very sticky. We never had a real churn problem there. We had other problems, but we never had a churn problem."

What made the difference was paying attention not just to what was working, but why it was working. Not the high-level metric of "we closed Home Depot and they're paying us a million bucks." But what was actually driving real usage underneath.

The Carbon Health Interlude

After selling Dynamic Signal around 2020, Russ would normally have immediately started another company.

But it was the height of COVID. He hated remote work and didn't want to start a fully remote company.

A long time ago, Russ had been the first investor or one of the first investors in Udemy, the education platform. That founder, Aaron, had started a healthcare company called Carbon Health that was growing quickly.

"Aaron wanted some help and I did not want to start another company at the time," Russ said.

So for about two years, he went and helped Aaron and the team at Carbon Health. They raised hundreds of millions of dollars scaling the business during a critical growth period.

By about eighteen months ago (mid-2023), Carbon didn't need full-time help anymore. Russ was ready to start something new. His long-time collaborator Jim Larrison, who had stayed inside the private equity firm running Dynamic Signal, was also ready to leave.

The band was getting back together.

Starting Larridin: AI Measurement in the Enterprise

"I was always going to start something new," Russ said. "I'm still not yet fifty. I'm sure there will be a point where I stop being a founder, but that point has not arrived yet."

The question was: what to build?

Russ started from first principles: "It is so hard for any of these things to work. What are Jim and I actually good at? Where do we have a potential unfair advantage?"

They'd spent thirty years selling expensive software to big companies. They knew measurement and third-party measurement from Comscore. They knew employee experience and engagement from Dynamic Signal.

The insight came from watching the AI explosion: anytime lots of money moves from one category to another—client server to cloud, TV advertising to online advertising—there's an opportunity to build a large third-party measurement company.

After talking with thousands of former customers and partners, Russ and Jim heard the same thing repeatedly from CEOs, CFOs, and heads of HR: current tools to measure and understand corporate productivity are severely outdated and not helpful in a world of AI.

Companies don't just tell twenty thousand employees "here's CoPilot, go use it." There are questions:

• Are people actually using these tools?
• Which tools are being used?
• Which tools aren't being used?
• Most importantly: are they making people more productive?

72% of enterprise leaders believe AI is impacting profitability, but 55% are unsure if their investments are paying off, and nearly two-thirds admit to having lost visibility into their AI stack, according to a Larridin survey of 350 senior finance and IT leaders.

"General Mills is not spending what they're spending on AI because they think it's fun," Russ explained. "They're doing it because they think it will drive more productivity."

Larridin raised $17 million in seed funding led by Andreessen Horowitz with contributions from Gradient, Bloomberg, Haystack, Homebrew, and others.

The company didn't start building until January or February 2024. They didn't start selling until August. They didn't hire any sellers until August.

As of the podcast recording (likely late 2024), Larridin had 20 total employees, four sellers, and tens of customers.

"I feel great about where we are, but it is early," Russ said. "It is still very early for us."

Lessons From 30 Years of Finding Product-Market Fit

1. Have conflicting ideas in your head simultaneously

"You have to project extreme confidence that what you're doing [will work]—it's a miracle any of these things ever work," Russ explained. "But you also have to be very quietly worried that you're completely wrong and open to any proof point that you are wrong."

This duality is essential. Project confidence externally to attract talent and capital. Maintain radical openness internally to evidence you might be wrong.

2. You don't have product-market fit until people give you money

"You can't really believe you have something until people are actually paying for it. On the consumer side, actually using it—there's a reason repeat rate matters," Russ emphasized.

With Social Shield (a parental monitoring company he co-founded), people loved the idea in research. They said they'd definitely use it. Then when offered for free, they wouldn't even install it.

"It is great to get excited about what people tell you, but a lot of people just want to be nice and helpful. You can't really believe you have something until people are actually paying for it."

3. The multi-time founder paradox

"One of the problems you have when you're a multiple time founder is everybody likes your idea," Russ said.

First-time founders struggle to get anyone to listen. Multi-time founders get the opposite problem: everyone tells them their ideas are great because of past success.

"Jim and I were smart enough to know that whatever people told us, none of it was truly true until we brought them something and said, will you give me money for this?"

4. Make new and exciting mistakes

"My mantra is you should try and make new and exciting mistakes, not the same mistakes you made last time," Russ said.

At Dynamic Signal, they succeeded too early and easily because of their Adify success. This actually cost them years because they kept selling something that worked but wasn't a great software idea.

At Larridin, they've been careful not to fully believe things people tell them until asking for money.

5. Product-market fit is never a destination

"I actually reject the idea that there's product market fit and then it's magical," Russ said. "All of these great businesses constantly reinvent themselves all the time."

Microsoft's thirty-year history shows constant reinvention. Google today is vastly different from Google in 1996. Even with product-market fit, some companies cap at $100 million, others at $1 billion, others at $10 billion.

The difference isn't just luck or the product growing automatically. It's constant reinvention.

"It's much more like tacking when you're sailing or you're lost in the forest, just finding your way, finding your way, finding your way."

6. Start from your unfair advantages

Given how hard it is for startups to work, Russ always starts from: what are we actually good at?

For Larridin: they're good at selling expensive software to CIOs at big companies. They know measurement. They know employee experience. They don't know security, so they didn't build a security product.

"I really think about where do we have some potential unfair advantage, given that it's so hard to make anything succeed ever."

7. Time is the only real risk

"As long as you're following the law, the only thing that is really a risk when you're a founder is wasting your time," Russ reflected.

He spent only a year at wine.com and looks back fondly because he only wasted a year. If he'd spent six years, it would be pathetic.

"My career is not over, but it's closer to over than it ever has been. It's funny to sit here talking about stuff over the last thirty years, because I remember it like it was yesterday."

8. Pay attention to emergent behavior

The Dynamic Signal pivot happened because they paid attention to what was actually working, not what they thought should work.

"It wasn't just paying attention to what was working. It was paying attention to why it was working," Russ emphasized.

Not the high-level metric but the underlying drivers. What's actually going on that's driving real usage?

9. Productivity measurement requires both behavior and attitude

At Larridin, they're taking the approach that's existed for sixty years: combine observed behavior and actual metrics with attitudinal behavior through employee pulse surveys.

"Productivity research is this interesting thing that's been around for the last sixty or seventy years. McKinsey has a multi-billion dollar business called the Corporate Health Index."

You need to know what tools people are using and how much, then overlay attitudinal components. Are the people using these tools more productive at their jobs than people who don't?

10. The fundraising advantage compounds

"It is definitely true that compared to the last thirty years, if you're a multi-time exited founder and you're doing something in AI, it's a good time to raise your first round," Russ admitted.

He wanted to raise $10 million. The first person he talked to at Andreessen wanted to invest. "That was great."

Why did he stop at $17 million instead of $25 million or $40 million? "We kept letting friends in and then at some point we said, okay, that's enough."

The data proves multi-time founders are better bets on average, even though plenty of first-time founders will outperform them.

Frequently Asked Questions

Who is Russ Fradin?

Russ Fradin has 30+ years of experience in Silicon Valley, starting as VP of Business Development at Flycast Communications from 1996-2000. He was EVP of Corporate Development at Comscore Networks, co-founded Adify Corporation (sold to Cox Enterprises), and co-founded Dynamic Signal.

What is Dynamic Signal and what happened to it?

Dynamic Signal was a mobile-first company communications platform founded in 2010 by Russ Fradin, Steve Heyman, and Jim Larrison. The company merged with SocialChorus in 2021 to form Firstup.

How much revenue did Dynamic Signal reach?

Dynamic Signal reached approximately $50 million ARR before being acquired around 2020. The company served hundreds of enterprise organizations including more than 20% of the Fortune 100.

What was the Dynamic Signal pivot?

Dynamic Signal started as an influencer marketing platform for bloggers but discovered that employees (not traditional influencers) were the ones consistently sharing company content. This led to repositioning as an employee communications and advocacy platform.

What is Larridin and what does it do?

Larridin is a platform that enables organizations to continuously measure and optimize the productivity of humans working alongside AI. It helps companies understand what AI tools are being used, by whom, and whether they're actually driving productivity gains.

How much funding has Larridin raised?

Larridin raised $17 million in seed funding led by Andreessen Horowitz with contributions from Gradient, Bloomberg, Haystack, Homebrew, and others.

When was Larridin founded?

Larridin was founded in 2024, with the company starting to build product in January/February 2024 and beginning sales in August 2024.

What's Russ Fradin's advice on product-market fit?

"You can't really believe you have something until people are actually paying for it on the consumer side, actually using it. It is great to get excited about what people tell you, but a lot of people just want to be nice and helpful. If not [paying or using], it doesn't mean you're failing, but it means you have a lot of work to do."

How did Russ know when to pivot Dynamic Signal?

Russ noticed that despite having millions in ARR and happy customers, the influencer marketing business wasn't sticky. Customers treated it like media buys, not recurring software. Meanwhile, employees sharing company content showed true engagement without constant effort to recruit or retain them.

What companies has Russ Fradin founded?

Russ co-founded Adify Corporation (2005-2010, acquired by Cox), was Chairman of SocialShield (2009-2012), and CEO & Co-Founder of Dynamic Signal (2010-2020). He also held executive roles at Comscore, Wine.com, and Flycast Communications.

Want More Founder Stories Like This?

This article is based on an episode from The Product Market Fit Show, where host Pablo Srugo interviews successful founders about their journeys from zero to PMF and beyond.

Listen to the full conversation with Russ Fradin to hear more about why Social Shield failed despite perfect market research, his philosophy on when businesses should constantly reinvent themselves, and why he thinks it's miraculous any startup ever works.

🎧 Listen to the episode here