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I started out indie hacking, now I've built 3 venture-backed SaaS companies, sold two, and raised over $40M for the latest. AMA.

Hi all, Bob Moore here. I'm currently CEO of Crossbeam (crossbeam.com) and formerly co-founded RJMetrics and Stitch Data.

I'm an indie hacker at heart and still spend a lot of my time on growth hacking, SEO, content marketing, and lean software development. Also a strong believer in "finding the global maximum" for my companies by putting outside funding to work.

Quick rundown on the journey so far:

  • 2004-2006: Built a poker software odds calculator in my dorm room, grew it to ~$10k MRR using SEO and AdWords
  • 2006-2008: Worked as an Analyst in a Venture Capital firm focused on software
  • 2008-2016: Co-Founded data analytics SaaS company RJMetrics, which eventually raised ~$25M of VC and sold to Magento (now Adobe)
  • 2016-2018: Co-Founded data infrastructure company Stitch Data, sold to Talend after two years
  • 2018-Present: Co-Founder of Crossbeam, an escrow service for data that helps companies find overlaps in their data sets to build stronger and more actionable partnerships.

AMA.

  1. 3

    Inspiring! You've had a successful run. How did you establish the problem to start working on for these 3 different companies that you've co-founded?

    1. 5

      Thanks Hugh! In every single case, it's been pattern recognition at my previous job:

      • RJMetrics was based on repeated observations at the VC firm (their portfolio companies didn't have in-house ability to do cohort analysis and CLV analytics)

      • Stitch Data was based on one of the big infrastructure challenges we faced at RJMetrics (data pipelines are painful to build and really high maintenance)

      • Crossbeam is based on a pain point I felt at RJMetrics and Stitch (partner collaboration isn't data driven because of disparate data sets)

      In all cases, because of this pattern, I was fortunate to have at least a small pool of future users/customers right out of the gate who could give us feedback, beta test products, etc.

      1. 1

        I see - so always identifying the problem first and then building from there. Thanks for sharing!

  2. 1

    @bobmoore Thank you for doing this! Couple of questions

    1. Could you give a little bit of info about your background? Did you start out with coding skills, business, networking?
    2. What is the most important skill that helped sale and create so many companies?
    3. What is the hardest part about being a serial entrepreneur?
    1. 1
      1. I was an engineer first, starting out on the coding side. The business stuff was always fascinating to me, though, and most often my motivation for taking on a coding project had more to do with the potential business applications than the coding itself. So the two really went hand-in-hand. Ironically, I started out way better at coding than business but today I don't code at all and the business stuff is my whole job.

      2. Intellectual curiosity. The ability to get fired up about new ideas, collaborating with smart people, and loving the feeling of winning.

      3. I'm overextended and have a false sense of urgency to everything. It's good for business, especially at the early stages, but can mean I overextend or overcommit myself unnecessarily and end up regretting it. Working hard on doing better here.

  3. 1

    How did you get your role at the vc firm and how much of an impact did that job have the rest of your journey?

    1. 1

      The firm I worked for is called Insight Partners and they had a somewhat unique model in that they were targeting more mature companies that already had traction. As a result, the traditional "company pitches VC" model was flipped, and a lot of their energy was spent "sourcing" deals by finding interesting companies and convincing the founders to take on a new investment. (By the way, Insight has grown into one of the most prolific VC firms in existence and this model has since become much more commonplace throughout the VC universe.)

      Anyway, I was able to get a job right out of college because they were hiring for "Analysts" who, in essence, were kind of like entry level sales reps. Only difference is that what we were selling was money. I called CEOs, sometimes to the tune of 100 per week, aiming to learn more about their businesses and find compelling deals for the firm.

      Honestly, I think the reason I got the job offer is because of the poker odds software business I ran in college. It gave me a unique perspective on the business and technical sides of starting a software company that helped me be more genuine and less salesy when talking with founders.

  4. 1

    Thanks for doing this, awesome resume. From an SEO perspective what were some of the most impactful decisions you made when you were getting early adopters?

    Also with a lower domain authority where in the monthly search volume spectrum per keyword range should I be focusing on to start to build monthly traffic?

    1. 2

      From an early decisions standpoint, I honestly think the smartest thing I ever did was start. It can be very hard to build conviction around SEO in a world where you are starting from nothing, might miss payroll next month, and see SEO as something that pay the most dividends years in the future. But it's one of those fuses you have to light super early so that it can burn, and once you see it working you wonder "why didn't I start this a year earlier?"

      I'm not deep enough in the SEO game at this point to answer your question about volume per keyword, so I won't fathom a guess. I suspect there are much smarter people here than me on that subject who might be able to chime in.

  5. 1

    Indie hacking vs Venture backed . Which one would you do if you could go back. Which one would you do going forward. Why ?

    1. 2

      Indie hacking first to learn the mechanics and fundamentals of growth, how to know it when you see it, how to appreciate the levers that make it speed up or slow down, etc.

      But, for me, once you have the muscle built to understand and harness growth mechanics, the opportunity to build something that has significance beyond personal enrichment is far greater when you have financial backing that de-constrains growth and creates incentives for you to generate the biggest possible version of your vision. It's a personal choice though and your take on it may evolve over time as you experience more things -- this is just where my journey has me right now mindset-wise.

  6. 1

    Congrats 3 times for founding something successfull 3 times in a row !

    How your typical day looked like at the beginning of each of your 3 companies ? How did you keep up with what you should do on a daily basis ? (tools, methods, influencial readings or else)

    1. 2

      At RJMetrics I was the technical co-founder so I spent a huge amount of my time writing code and spent very little time with customers and prospects (my co-founder owned sales and support). That was a big mistake, because I think it stayed in the DNA of the business for years, even after I stopped coding and focused more on strategy as CEO I never spent enough time with customers.

      At Crossbeam I hired a Chief of Staff as one of my first team members, and a lot of "have to do it but it doesn't impact the product" stuff (taxes, legal, real estate, company formation, etc) was put into her scope. I also had a true technical co-founder/CTO who owned the engineering team. That meant all my time could be spent with people outside the business, namely people who fit the persona of our eventual customer, and eventually that became our earliest "sales calls" (although I'd always position them as trying to get feedback on the idea, recruit early testers, etc.) It's made a profound difference in customer satisfaction and the strength of our PMF.

  7. 1

    Congratulations, this is really inspiring! You talk about "finding the global maximum", so I have two questions, if you don't mind:

    1. What indicators you use to know if a company will do better with VC vs going fully-bootstrapped?
    2. What's your advice regarding finding the "best moment to sell"?
    1. 2

      Love these questions.

      1. I'm always looking at the constraints that exist on the business relative to the validation we've got that the opportunity is larger than we can currently capture. For example, if we have extremely healthy lead gen channels and customer retention numbers, but the payback period on customer acquisition is long, infusing capital into the business can ensure we don't leave deals on the table just because of hard cash constraints. Similarly, if we have validation that building specific features sooner will give us a competitive edge or access to a validated market segment with a limited time window of opportunity, investing in R&D (i.e. hiring more engineering resources) and increasing burn may be justified.

      On the flip side, money doesn't actually solve any real problems. It doesn't give you product market fit, it doesn't improve company culture, it minimally impacts you closing big deals or candidates. It is purely a force multiplier for companies where everything is already working well. Founders who try to raise money to patch holes in the foundation of their business are going to have a rough ride.

      1. I have a very dry, free market capitalist answer to this: We will sell the company the minute someone offers us more than we think it's worth. Now, keep in mind that no one on the planet knows more about the past, present, and future of this company than the founder/CEO, so I can bake in tons of proprietary knowledge into my calculus about what it's worth, what its potential is, which risks to discount by, etc.

      For a company like Crossbeam, I'm so excited about the potential that the price I'd demand would be completely detached from the actual realities of the business, so there's no way it'd sell near term. In any case, as companies mature, those lines tend to converge a bit and opportunities for transactions get more common.

  8. 1

    How did you acquire customers for your poker business? You say SEO and AdWords, but bow much did you spend? What was CAC? Etc

    1. 2

      This was 2004-2006ish and AdWords was relatively new and far less competitive than it is today -- I bought ads for search terms like "how to win at poker", "odds of getting four of a kind", "poker odds calculator", etc; (Similarly on the SEO front I just had simple landing pages for the same families of keywords.) I was paying 10 to 50 cents per click and converting to a $30 sale at 5-10% conversion rate. So CAC was max $10, and ACV/CAC was 3:1 at worst.

  9. 1

    Impressive Bob! Congrats on those successes.

    I'm startin g aSaaS Venture too and I'm wondering, could you share one specific growth hack that has helped you more than anything with your distribution?

    Thanks

    1. 1

      Microsites.

      Early on in the life of each business, we accumulated available domain names that were close matches to the long-tail search terms we thought would be most used by people in our target markets. At RJMetrics this was stuff like cohortanalysis.com and churn-rate.com (both of which are now sadly defunct I believe).

      At Stitch, this was more complex networks of sites like the www.toredshift.com domain and its dozens of subdomains, which drove people who were searching for terms like "mysql to redshift"

      At Crossbeam it's the work we're doing at partnerbase.com to create directory listings of partnerships for every B2B company on the planet. (Mapping to search terms for "X partnerships" etc).

      These start out really small and slow, almost feeling like a waste of time and effort, but over the course of running a company for 2,3,4 years and beyond they grow into massive traffic powerhouses that are force multipliers for the core business. You just have to have a really long term time horizon and not let them languish.

  10. 1

    Impresive !
    about Stitch Data , first can you share which teh stack did you used for the ETL ?
    Also how come it was sold after 2 years ? ( very fast)

    1. 1

      We were totally hosted on AWS over at Stitch, and the code was mostly built in Clojure. In terms of where we sit in the modern data stack, we were most commonly used alongside BI platforms like Looker, data warehouses like Snowflake, and data transformation tools like dbt.

      Honestly we probably sold the company too soon, as the ETL space has really continued to heat up and gain momentum since that transaction. But a really great acquirer who we liked and felt aligned with made us an offer that we found very compelling, so we decided to go for it.

      1. 1

        @bobmoore may I ask why did you choose Clojure and how happy you are with your decision?

  11. 1

    How do you deal with (if you find it a challenge) the difference between doing indie work (very hands-on - doing pretty much everything) to VC high growth companies with bigger organizations (a lot of people issues, less hands-on, more "corporate", etc)?

    1. 4

      Great question. In the early days of each startup, it probably feels more like an indie hacker environment than a VC funded startup. We hire very small teams and focus on "T-Shaped" people (meaning they can go deep in one particular area, but have skills they allow them to cover extremely wide horizontal areas of the business and are willing to wear many hats). Over time, as things start working, you can start hiring people that are more and more specialized, add management layers, and focus on the things that allow for scale and predictability (and the T shaped people can focus in on the deep part of their T).

      So, in other words, it's less of a "flipping a switch" between the agile indie mindset and the big corporate one, and more of an evolution that happens as the needs of the company require it.

      YMMV but to me this is actually one of the most fun parts of scaling a company. It gets a little easier every time as you accumulate muscle memory / scar tissue that lets you do a better job of predicting how things will play out if things go well.

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