[SaaS Club] From Bootstrapping Struggles to a $60M Exit and Beyond

The SaaS Club Newsletter


Hey Reader


Here's a quick round up of what's been going on at SaaS Club:

 In this week's newsletter:

  • 🎧 From struggles to a $60M exit & beyond

  • 📈 Financing options for buying/selling SaaS

  • 👩‍💻 Jotform Tables: Smarter than spreadsheets

  • 🤔 Selling opportunities vs. learning opportunities

  • 📗 Book picks: growth strategies and sales acceleration


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🎧 Podcast


From Bootstrapping Struggles to a $60M Exit and Beyond


Bob Moore is the co-founder & CEO of Crossbeam, a SaaS platform that helps companies find overlapping revenue opportunities with partners.


In 2008, Bob and his co-founder Jake started RJ Metrics, a pioneering cloud analytics platform, which they bootstrapped for the first 3 years.


Those early years were grueling as the founders struggled with to find product-market fit, acquire customers, and keep the business afloat.


Despite being early to the market, by 2012 they found traction, grew the business, and raised over $20 million in venture capital.


However, in 2015, their business model was disrupted and the company stopped growing. Luckily, they were able to sell the company - although Bob described it as a 'good but not great exit'.


In 2016, Bob and Jake spun out a piece of RJ Metrics' technology used for moving data between systems into a new company called Stitch.


In a whirlwind 18 months, thanks to some good fortune and timing, they sold Stitch for $60 million - a much more successful exit this time.


But Bob wasn't done yet. 


In 2018, he co-founded Crossbeam, a partner ecosystem platform to help companies build more valuable relationships with their partners.


But he quickly realized he had a huge issue.


His platform was useless unless he could get both the company and its partner to sign up simultaneously.


"It was like landing two jumbo jets at once!" he said.


This made it extremely challenging to grow the business.


Despite the hurdles, Bob and his team persevered. Leveraging their network, they onboarded early adopters, and after two years of hard work, the network effect kicked in, helping to fuel growth.


Today, Crossbeam generates eight-figures in annual recurring revenue (ARR) and serves nearly 20,000 companies. Their team has grown to over 100 people, and they've raised $116 million in VC funding.


In this episode, you'll learn:

  • How Bob and Jake survived 3 grueling early years of bootstrapping when they were 'broke' and struggling to acquire customers.

  • How the founders spun out a piece of RJ Metrics' IP into a new company, leading to a successful $60M exit in just 18 months.

  • How Crossbeam overcame the cold start problem in building a two-sided marketplace where they had to onboard customers in pairs.

  • What specific lessons from RJ Metrics and Stitch Bob applied to navigate pivots, find product-market fit, and scale Crossbeam.

  • Why Bob believes solving a problem you've experienced firsthand and selling to an audience you know well are critical to success.

I hope you enjoy it!


Listen to the full podcast episode


📈 Boopos: Buy a Profitable Business or Sell Yours


Boopos is the #1 platform for buying & selling a profitable online business and the first to offer built-in acquisition financing for qualified buyers.


Explore their exclusive listings, browse listings from other marketplaces, or submit your own deal for approval. 


Boopos offers pre-approved financing for recurring revenue businesses, allowing you to access fast funding with no personal guarantees. And their experienced M&A advisory team supports you every step of the way.


Sign up today and get qualified to start your entrepreneurial journey or sell your business at the right valuation.


Learn more about buying or selling a SaaS business



 👩‍💻 Jotform Tables: Beyond Spreadsheets


Jotform Tables combines the power of a spreadsheet with the flexibility of a database, allowing you to collect data via customizable online forms. 


All data submitted through your Jotform forms is automatically organized and stored. You can import and export files, and collaborate with your team in real-time, ensuring everyone is always on the same page.


But Jotform Tables is more than just a spreadsheet alternative. With data visualization, conditional formatting, and 250+ integrations, it's a complete productivity platform for your team. You can even automate tasks and workflows to save time.


Create a Jotform Table - It's Free!


🤔 Selling Opportunities vs. Learning Opportunities

Many SaaS startup founders are missing a huge opportunity. 


They (and their team) are not asking enough questions during demos.


Instead of using all the time to pitch your product, use more of that time to learn about your customers.


Understand their desires, pains, and behaviors. 


Ask questions. 


Make each demo a learning opportunity about your customers.


I once advised a company where the leadership decided to focus the marketing message on a specific problem.


Marketing team spent over a month on new messaging and campaigns.


But a curious sales rep who was asking good questions during demos luckily helped uncover a surprising truth.


The problem they'd built their entire strategy around wasn't actually a top priority for most customers.


This one insight saved the company from pouring more time and money into the wrong strategy.


→ So, ask more questions during demos.


Don't just view demos as a 'selling opportunity' to close a sale. Treat them as a 'learning opportunity' to deeply connect with customers.


Ask more and learn more. Eventually, you'll sell more


Want my help to turn more demos into customers? We'll work together one-on-one to uncover laser-sharp customer insights that boost your demo conversion rates. Reply "demos" for more deets.


 📗 Book of the Week


This week's books recommendations are from Bob::


Ecosystem-Led Growth: A Blueprint for Sales and Marketing Success Using the Power of Partnerships by Bob Moore


The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go from $0 to $100 Million by Mark Roberge



🌟 Help Spread the Word


Enjoyed this week's newsletter? Please do me a favor and forward this email to someone who would benefit from it as much as you did. 


Sharing is caring, and it helps us grow! ❤️


😍 Let's Get Social

Want to get more social? Follow me on Twitter or LinkedIn.


Have a great week!


- Omer

Interested in sponsoring The SaaS Podcast or this newsletter?


P.S. Whenever you're ready, here are 4 ways I can help you:

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  2. Apply for SaaS Club Launch: Designed to accelerate your journey to $10K MRR for new and early-stage founders.

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