In this episode of the SaaS Revolution Show, host Alex Theuma is joined by Larry Kim, Founder and CEO at Customers.ai. 

“With the benefit of hindsight, it could have been done with even less than $18M. I think what happens is when you raise money, it allows you to make bets that you might not have otherwise made had you been operating on the edge of a knife.”

In the 35 minute episode, Larry shares: 

  • How he transformed a consulting business into a $55M ARR SaaS company.
  • The content marketing strategy that generated 50,000 leads per month.
  • Lessons from his $150M exit to Gannett (USA Today’s parent company).
  • Why traditional inbound marketing is no longer effective in 2025.
  • How his new company, Customers.ai, is reshaping digital marketing and lead generation.
  • His learnings on bootstrapping vs. raising venture capital.

Watch (or listen) below or read on for key takeaways.

Listen to the audio:

From solopreneur to SaaS founder

After graduating college in 2008, Larry Kim started working as an online advertising consultant:

“That was a great business, still is, but even more so then because a lot of those new channels like PPC were a little more mysterious…You could charge $5-10k retainers for ten clients and that’s a lot of money for a person in their early twenties.”

Though successful, he quickly “maxed out on capacity” and started to build automation tools that could manage some repetitive keyword research tasks and campaign management admin.

Then came the “lightbulb moment”

“I saw other companies raising hundreds or tens of millions of dollars to enter those solution spaces… and I just thought, what the heck? This is my big opportunity. Why not just sell the stupid automation tools that I was using in-house, rather than doing a straight services company?”

Running the SaaS side of the business with revenue from consulting allowed Larry to hire marketers, salespeople, and engineers early on. It also gave him “a test bed of clients” to work with.

Raising a $4M Series A

After bootstrapping initially, WordStream raised a $4M Series A. But it wasn’t a simple process:

“I started pitching all these venture companies. It wasn’t as easy as it is to do now because it didn’t have all the SaaS communities or the venture communities established, it was just like emailing the front door.”

After ~100 pitches, seven meetings, and two offers, the $4M round closed in September 2008.

Despite generating revenue through the consultancy side of the business, Larry opted for the venture route due, really, to “fear of missing out (FOMO),” he said:

“There were other competitors that were raising money with big name VCs. I just felt that it was now or never, this is not something that I can revisit a year from now.”

On reflection though, Larry realised that the venture route comes with trade-offs: 

“Raising money allows you to make bets that you might not have otherwise made…It allows you to find those errors faster but it’s a little less efficient because you’re bumping into things along the journey.”

For WordStream, it was the right choice and helped them to scale to $55M ARR.

Scaling WordStream to $55M ARR

After the Series A, Larry thought he “won” but soon realised that “churn was too high and the market was too down market.”

Turning things around was a decade long journey with some key learnings:

Solving product-market fit (PMF) challenges

Knowing there was a PMF problem, Larry found there were two options–change the market or change the product:

“We could either change the target market to be bigger companies or keep the product aligned with the leads that were coming in the front door. We chose the latter.”

Instead of moving upmarket, WordStream simplified its product, shifting from complex keyword research tools to more intuitive ad campaign management software.

Creating inbound through content marketing

With the product in a good place, WordStream went heavy on content marketing, creating what Larry calls a “publishing empire” to power it’s next stage of growth. This included: 

  • Publishing a high volume of articles and how-to-guides on growth marketing.
  • Syndicating this content on major platforms like Medium and news sites like CNBC. 
  • Distributing this content via social media, organic as well as Facebook and Google ads.

And the results speak for themselves: 

  • Content drove 3-5M visitors to the WordStream website.
  • Larry remains a top publisher on Medium and has 90K+ followers on LinkedIn.

Navigating the exit process

By 2018, WordStream had reached $55M ARR and $16M EBITDA. With such a strong cash position, the board started to look at its options:

“Do we invest in new markets and then try to triple the product lines and then get more share of wallet? Do we acquire businesses with this humongous pile of cash? Why don’t we try to get some optionality and test the market to see what the market might value an asset like this?”

Running the process

WordStream chose to employ investment banking firm Houlihan and Lokey to help them explore potential buyers.

They made inquiries with private equity companies and saw some quick results. Those term sheets were then used to create urgency from more strategic partners and buyers.

“Ultimately, there were a couple of firm offers towards the end of it and we went with Gannett.”

Gannett acquired WordStream for $150M (close to $200M including escrows, earnouts, and cash in the bank).

Learnings

Though the results speak for themselves, Larry wonders if deeper strategic partnerships could have commanded a higher multiple:  

“In the back of my head I wonder, had I forged more strategic partners, could we have done things with Salesforce et cetera and become more essential to those other ecosystems?”

The lesson here is to think about the exit from day one of running the business.

Why Larry started Customers.ai

Shortly after leaving WordStream, Larry moved on to his second (and current) business, visitor identity resolution tool, Customers.ai. 

“Typically form fill rates are low, single digit percentages. With website visitor identification you can actually get substantially more of these identities, without people filling out the forms.”

His interest in this came from a decade working with over 10,000 customers at WordStream who struggled to make ad campaigns profitable. Instead, they were “loss leaders” and he wanted to fix that.

Building a second business: What’s different this time? 

A new GTM playbook: 

According to Larry, the broad SEO-inbound approach he used at WordStream just isn’t as effective for businesses today. In 2025, your GTM requires a more targeted approach: 

“It’s flipped on its head. It’s much more about an account-based focus rather than a broader SEO, PPC strategy. It’s much more intentional to go after a very specific audience.”

For this, Customers.ai uses personalised email and targeted ad campaigns, as well as using conferences and their network to meet prospects face-to-face..

Fundraising with efficiency in mind:

In total, WordStream raised $18M but Larry’s taking a more measured approach at Customers.ai:

“I don’t believe that you need to raise these enormous amounts. Customers.ai did a Series A, it was only $5M.”

In 2024, the focus was on efficiency and they eliminated a “six figure monthly burn.” Now, they can push for key growth and revenue milestones before having to raise again. 

Solving a more complex engineering problem

Unlike WordStream—which was largely an operational challenge—Customers.ai is solving a much more difficult engineering problem: 

“Most visitor identification tools have poor accuracy (5–30%). We’re pushing for 70–80% accuracy, which is a massive engineering challenge.”

Success no longer depends just on execution in sales and marketing—it requires true technical innovation.

Hear more from Larry Kim at SaaStock USA (13-14 May)

Larry is joining our stellar lineup of speakers including Mike Tessler (True  North Advisory), Alina Vandenberghe (Chilipiper), and Matt Mullenweg (WordPress) on the Founderpath Center Stage on the 14 May. 

In his keynote, he’ll share how he learned that timing is everything when it comes to an exit and how to identify when to sell. 

You don’t want to miss it. 

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