Bootstrapping to $15m by finding product-market fit (📈 MTN #08)

Author's avatar Move The Needle UPDATED Feb 20, 2024 PUBLISHED Apr 18, 2023 10 minutes read

Table of contents

    Peter Caputa

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    In this edition

    • 📊 Facebook Ads benchmarks
    • 💡 Where should you spend $2k on ads?
    • 📈 Bootstrapping to $15m+ by finding product-market fit

    📊 Featured Benchmark Data (from Benchmark Groups)

    Facebook Ads Benchmarks for B2B (March 2023)

    • Reach: 108k
    • Frequency: 2.9
    • Clicks (all): 3.14k
    • CTR: 1.27%
    • CPM: $6.74
    • CPC: $0.48

    Join this group to see how your company stacks up. See if you’re ahead or behind the curve, and where you can improve.

    💡 Trends & Insights (from Reports & Surveys)

    If you had just $2k/mo to spend on ads, should you spend it on LinkedIn or Facebook?

    According to our data, it looks like B2B companies spend roughly the same on LinkedIn Ads as they do on Facebook Ads. Last month, the estimated amount spent on Facebook Campaigns was $1,347.95. For LinkedIn, it was $1,660.91. 

    And since lots of B2B companies have tight budgets, we wanted to help them learn what the best use of $2k in ad spend might be, if they had to choose just 1 of those platforms.

    To do that, we surveyed 48 companies and found a few interesting takeaways:

    For brand awareness, the majority (80%) use Facebook Ads, while only 40% use LinkedIn.

    For retargeting, 60% use Facebook Ads, and 40% use LinkedIn.

    In fact, most respondents said Facebook outperformed LinkedIn when used to either build brand awareness or retarget prospective customers.

    For direct response campaigns (ads that try to get the viewer to take direct action), companies felt both platforms performed equally well.

    📈 Drive Predictable Performance (from Metrics & Chill)

    Finding product-market fit to bootstrap to $15m in ARR.

    The idea of product-market fit (PMF) can be distilled down to this: building the right thing, for the right customer, and offering it at the right price.

    When those things align you stand to experience incredible growth.

    Andy Rachleff (who is attributed with developing the idea of PMF) has this to say:

    On what it is…

    “A value hypothesis is an attempt to articulate the key assumption that underlies why a customer is likely to use your product. Identifying a compelling value hypothesis is what I call finding product/market fit. A value hypothesis identifies the features you need to build, the audience that’s likely to care, and the business model required to entice a customer to buy your product. Companies often go through many iterations before they find product/market fit, if they ever do.” 

    He goes on to say…

    “If you address a market that really wants your product — if the dogs are eating the dog food — then you can screw up almost everything in the company and you will succeed. Conversely, if you’re really good at execution but the dogs don’t want to eat the dog food, you have no chance of winning.”

    OK, so how do you find it?

    “You often stumble into your product/market fit. Serendipity plays a role in finding product/market fit but the process to get to serendipity is incredibly consistent.”

    And how do you know when you’ve found it?

    “You can always feel when product/market fit isn’t happening. The customers aren’t quite getting value out of the product, word of mouth isn’t spreading, usage isn’t growing that fast, press reviews are kind of ‘blah’, the sales cycle takes too long, and lots of deals never close. And you can always feel product/market fit when it’s happening. The customers are buying the product just as fast as you can make it — or usage is growing just as fast as you can add more servers.”

    So according to Anthony, you’ve achieved product-market fit when you build the right product and features for the right audience, at a price they’re happy to pay.

    And you know you have it when you spend more time handling growing pains than you handling the pain of not growing: hiring, fielding customer support requests, feature requests, etc.

    But it usually takes a lot of time and a few pivots before finding PMF. Andy points out there is that

    “companies often go through many iterations before they find product/market fit, if they ever do.”

    I recently got to chat with a founder who went through those painful iterations, and came out on the other side finding the elusive PMF. And as a result, he bootstrapped his business from $0 to $15+ million in annual recurring revenue (ARR) in just two and a half years. What’s more, he’s on track to hit $50m in ARR in the next couple of years, and building a $1b valuation company in public, sharing what he’s learning along the way.

    That founder is Adam Robinson, creator of

    It all started as a feature. started as a single feature in a different product. Adam was building an email marketing company called Robly when he learned it was possible to reconcile a visitor to an email address – even if they weren’t logged in. 

    It took him over a year to learn how to do it and build it into a usable product. When he did, he added it as a feature and rolled it into Robly in hopes it would help him differentiate from bigger competitors like Mailchimp.

    But then something interesting happened. Customers started coming and joining Robly just to use the email reconciliation tool. In fact, some customers would join, use the tool to export a list of emails, and then upload them into their existing email platforms.

    So eventually, he sold Robly and launched the email reconciliation tool as a separate product and business: “Get Emails”. This was the first major iteration on the road to finding product-market fit.

    The second iteration: narrowing the ICP to e-commerce

    After launching Get Emails as a standalone product, Adam was quickly able to scale it to $10k in MRR. At first, it showed incredible “top of funnel” PMF signs but there was no churn because the product was too young. 

    In fact, from day one it was easy to sell. The value proposition was clear: get emails from people who visit your site to market and sell to them, even if they’re not logged in. Most sales were driven by cold outreach. 

    Hypothetically, anyone with a website could get value out of Get Emails. But Adam found great traction early on with Shopify users. He had tested a number of Facebook ad campaigns and found one in particular, targeting Shopify customers, which showed high ROI and drove lots of immediate signups. But over time, they proved to be poor-fit customers and drove Get Emails’ churn rate to 20%. 

    Adam cut the ads, churn dropped to 6-7%, and he focused on e-commerce. The product was self-serve but also catered to enterprise-level e-commerce brands like Warby Parker. This helped him scale to $4m~ in ARR, but he still didn’t feel he had achieved PMF. Customers were paying wildly different amounts: $19/mo to $50k/mo and everything in between. Churn fluctuated between 6-8%, and he realized he couldn’t exceed $30m in ARR with that churn rate.

    But then, the third and final major iteration occurred.

    Finding PMF: retention tools for Shopify Plus brands

    The third and final big iteration as the one that led to finding the elusive product-market fit. There were two major contributors:

    First, Adam discovered a second use for their product: abandoned cart emails. Now that they primarily served e-commerce brands, being able to reach people who abandoned their shopping cart was a huge advantage. Normally, you can only email the user if they were logged in while shopping, which is a very small % of most shoppers.

    Second: Diana Ross (Co-Founder and CRO) found that a subset of their customers, big Shopify stores (Shopify Plus brands), almost never churned. Upon further research, she also found that not only was their churn rate exceptionally low, but they referred friends to the product (without being asked or prompted) and raved about the product.

    Armed with a new product and this new knowledge, they made 3 big changes.

    First, they doubled the value of the product for Shopify Plus customers: they started creating more features and products to better serve their “best customer”.

    Next, they reduced the price by two-thirds and pivoted to only selling annual deals. Formerly, these customers were paying $7,500/mo. With the move to annual deals, they lowered the price to an average of $2,500/mo. And because they had nearly doubled the value of the product, nobody even blinked at locking into longer contracts.

    And finally, they bought, and rebranded as “Retention for Shopify Plus Brands”.

    This final iteration and these three major changes led to finally achieving product-market fit. 

    Signs they found product-market fit

    One way Adam described finding product-market fit was, the team spends most of their time dealing with growing pains rather than trying to grow the company.

    They had to hire 40 people over 9 weeks. Adam’s call schedule was constantly booked with prospects.

    They had hit $15m+ in ARR with a clear path to $50m ARR. Their average deal size was $30k, and they boasted a 7-day sales cycle and a 90% close rate.

    In other words, it constantly feels like they’re struggling to keep up with the growth, rather than drive it. All problems they’re focusing on solving is how to deal with the demand, rather than driving demand. They’re drowning every week because of how much activity and desire there is for the product.

    And for Adam, finding product-market fit was the result of lots of painful iterations:

    “It was a combination of all that stuff that happened around Santos joining. The rebrand to, chopping our prices by two-thirds, adding a hundred percent more value and going annual at the same time, increasing focus to only going after the Shopify Plus guys – period – and no one else, and putting all of our energy and all of our messaging and everything out to that ecosystem, and the “brand heat” of the message spreading around.”

    Lessons learned along the journey to find PMF

    In the interview, Adam summarized a few takeaways he learned in his journey to find product-market fit:

    Be as different as possible. started as a feature in another app. Adam wasn’t trying to invent a new product, he was trying to differentiate. And he feels it’s crucial to identify and lead with what makes your company different. 

    Your intuition is not a good indicator of market viability.

    Every single day someone tells Adam they need to expand to serve B2B. But it doesn’t work. He’s tried. 

    Hypothetically, anyone with a website could use this product: B2B, political campaigns, you name it. But they went all in on the single audience that loved the product the most, and retained the longest.

    This leads to the next tip…

    Narrowing your ICP can drive growth (not hinder it).

    I think there’s an inherent, understandable fear around niching down to serve a specific audience. For many companies, it feels like they’re leaving an opportunity on the table. If many audiences could use your product, why position it to serve just one of them?

    In Adam’s case, niching down didn’t hinder growth, it drove it. He could build a more valuable product, attracted more of his best customer, and triple revenue. It doesn’t mean it’ll be the same for you. Every product is different, but it’s worth considering.

    If your business is meant to solve your own pain, you might get to PMF faster. 

    Adam was trying to figure out how to grow an email app, then stumbled upon this business. So he had to go through multiple iterations to find the right fit. But he feels you could probably shortcut that process if you started the product with the express intent of solving your own pain – one you understand well – for a dedicated audience.

    The journey of what you think your product will be is emotionally taxing. 

    At each stage, you’re getting certain signals that make your product is going to best serve this or that group of people. You’ll see spikes and dips. You’ll go down a road of a new product or audience thinking you’re on the right track, and then find that churn is too high and you have to backtrack. This is emotionally taxing, but with each iteration, you’ll learn more about who your product is actually for.

    The ultimate product-market fit sign: customers don’t churn.

    Adam noted that YCombinator teaches that ‘if customers are willing to endure a terrible UX and still use your product’ that’s an early, good sign of PMF. But Adam finds that the ultimate sign you’ve achieved PMF is that your customers don’t leave.

    Building a quality team is crucial.

    Adam wouldn’t have found PMF or built the right product as they did without experts like Santosh Sharan, who built data businesses like ZoomInfo and As a founder, you’re limited in what you can understand or focus on. So world-class talent will provide valuable feedback to help you know what to build, and how to go to market.

    Building the right thing, for the right audience

    Whether you’re served by the concept of product-market fit or not, you probably want to build the right thing for the right audience. Hopefully, Adam’s story can serve you as you strive to attract more of your best customer.

    Drive predictable growth

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    Jeremiah Rizzo

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