I bootstrapped Mailshake to 50k users and acquired 4 SaaS companies. AMA.

I run 5 SaaS companies (Mailshake.com , Warmer.ai, Voilanorbert.com, Rightinbox.com & Zoomshift.com) with 50+ employees all over the country.

I founded Mailshake and bootstrapped it to 50k users over the last 5 years. The rest of the companies I acquired along the way.

I started off as an SEO in 2001 and started a marketing agency (Single Grain) in 2008 where i learned to be a t-shaped marketer and how to (poorly) run a business. I sold the agency in late 2013 and took a job at a SaaS company (Wheniwork.com and helped it grow from $1M to $15M).

My goal was to learn everything I could about running a SaaS. I had a lot of free time on my hands going from running a business to being an employee so I found a developer and started a Mailshake.com (previously contentmarketer.io).

Mailshake took it sweet time to achieve product market fit so I got bored (again) and started buying SaaS companies and used my experience in sales and marketing to grow them.

Along the way my wife and I had 3 kids and moved to Austin, TX.

Don't let the sexy overview fool you. I made hundreds of mistakes along the way. Overtime I've learned to fail better and faster.

I'm an open book so ask me anything.

  1. 3

    The idea of buying a company and growing it is intriguing to me. Do you have any resources you recommend to learn more about this strategy?

    1. 2

      Here’s a few resources I wrote/recorded

      @jonhainstock has a good course on buying/selling companies (we bought Zoomshift from Jon and is partner Ben).

      Andrew wilkson of Tiny capital. Binge listen to every podcast interview he’s done

      Microacquire.com has some good starter resources and small companies you can buy.

    2. 1

      Its a lot more competitive now but still think there’s a good opportunity

  2. 2

    From all your Saas companies which one is the most profitable in term of pure revenue Also can you share info about your rightinbox app also in terms of revenue and markting
    how do you market such plug in ?
    what are your thoughts about the Gmail plugin market ? i for long time wanted to go into the email business..

    1. 1

      Mailshake is the biggest. Not sharing revenue or profits publicly. I prefer to quietly make money :)

      We have grown Right Inbox by adding new features, SEO and content marketing.

      Gmail plug-in/chrome extension space is pretty difficult..wouldn’t do it again. Little control over the sign up flow and Gmail/google love making changes without warning to the people who build on their platform

      1. 1

        Thank you very much for answering about the google market place .
        can you describe what Mailshake is doing ? im not from the markting/selling niche so the site dosn't tell me anythoing .....
        if you sending emails in Mailshake , do you mind telling which smtp provider you are using ?

  3. 2

    How you allocate your time between your 9-5 job and your side-projects (while on the start point)?

    1. 2

      These 5 companies are my 9-5 job. I focus on hiring smart marketer, sales and developers. I spend my time managing, coaching, leveling myself up and helping with problems my team can’t solve on their own.

  4. 2

    "..bootstrapped to 50k in 5 years" -- what was your MRR/ARR? Is the sales enablement SaaS space one with high overhead/customer churn? Whats it like selling to sales people, i'd think they'd be a great niche that is open to new things.

    1. 1

      We’re in the high millions of ARR. Not sharing our revenue publicly.

      Selling to sales people is pretty straight forward. I don’t see much of a difference with sale people vs marketers vs developer vs business owners. I focus on understanding my customers language and problems and trying to communicate in a way they understand/value.

  5. 2

    The latest company (Warmer.ai) just launched today on ProductHunt https://www.producthunt.com/posts/warmer-ai

  6. 1

    Really enjoyed your slides on slideshare - They're very informative!

    What was your customer acquisition strategy (or channel) for the first 10 customers you had, and did it change in any way after that milestone?

  7. 1

    What is the major advantage/disadvantage you can think of when running multiple SaaS products in parallel?

    1. 1

      Spread thin
      More stress
      More people to manage
      Switching gears is hard (this is something I enjoy)
      There’s always a fire to put out

      Less emotionally attached
      Learn fast
      Learn once, apply learning to all companies
      Diversified income/hedged bets
      Never gets boring
      There’s always something exciting going on ( new features, new record, new idea, etc)

  8. 1

    Did you follow any framework for finding and validating ideas? If so, could you share some details? 😊

    1. 1

      I don’t. I like buying companies that have PMF and are doing $1M ARR or greater

  9. 1

    What did you look for in the companies that you were looking to purchase? What was it about the ones that you ended up purchasing vs ones that you didn't?

    1. 1

      List of companies I didn’t purchase is tooo long. I typically look at 50-75 deals a month. I buy 1-2 companies a year.

      I look for companies I can 5-10x with my sales and marketing knowledge/experience. The space has to be big enough to achieve 50x growth snd ideally the space is growing.

      Traffic of company has to be stable/white hat. No affiliate or minimal ppc efforts.

      Small teams are great. Founder run is better.

  10. 1

    Hey Sujan,

    You mention you used your exp in sales to grow your businesses - what was your background and how was it relevant? What were some of your failures that ended up being lessons?

    1. 1

      My background is in marketing and I learned to do sales running my marketing agency. I also learned to work with sales teams to drive revenue working with clients and job at When I Work.

      Few failures

      1. Hire earlier than you need
      2. Fire fast
      3. Document processes
      4. Investing in training/leveling up your team
  11. 1

    I'm guessing you started MailShake as a solo founder. If yes, then at what stage did you start bringing other people in? Employees, Co-Founders? What was your method for that if any?

    1. 1

      Good guess but I started with Mailshake with a technical cofounder. Started bringing on people as we gained traction. I think it was when we hit $10k MRR.

      We spend most of our revenue to fuel growth.

      I Hiree people smarter than me and more specialized. Also want to hire people to run the day to day and grow the businesses with out me. My job is then team building, helping the leadership team and dealing with difficult problems.

      I’m in the weeds all the time but I’m focused on process improvements and challenges the way of thinking.

  12. 1

    I am a developer. How do I find a good idea for a side project.

      1. 2

        Validating a business idea is not my strength nor but I just start with finding a problem worth spending 5-10 years of my time on. Then Validate a solution that would be lucrative

  13. 1

    At what point in a SaaS company journey do you start investing in SEO?

    What are the best type of products to use SEO as a channel to acquire leads/customers?

  14. 1

    You've grown a few projects a lot, how would you grow Teamland? It's a virtual team-building company. website is https://ourteamland.com

    Our events are one-off and don't have that much of a recurring model (difficult to do).

    1. 1

      That's a loaded question. Email me sujitsu @ gmail.com

      Tell me about what you've done to date and a bit more about your space, competition and revenue.

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