Practical Founders Podcast

#66: Serial SaaS Founder Had Three Successful Exits in Three Different Ways – Raj Khera

Raj Khera has had three exits in his long career as a software entrepreneur and leader. His first company, GovCon, grew in the late 1990s to help government contractors easily access new contracts up for bid by the US government. Their advertising and subscription revenues grew quickly, and he sold GovCon in 1999 for $12.5 million.

He then bootstrapped one of the first email marketing software businesses in the early 2000s called MailerMailer to help small businesses send emails. Raj and his brother Vivek ran this as a profitable small business for many years, giving them an interesting business challenge while not sacrificing time with their families. After running the business for 15 years, Raj sold MailerMailer to a public software company, J2 Global, in 2017.

Then Raj joined a struggling VC-funded software company called WealthEngine to help grow sales, create new products and exit. Wealth Engine was successfully sold in late 2020. Raj is now an active advisor to software founders. At, he coaches software founders to efficiently acquire customers using advanced search engine optimization and marketing techniques.

SaaS Startup and Exit Topics Discussed on This Podcast 

  • Growing and selling a website media business in the late 1990s
  • Starting and running a lifestyle software company for 15 years to prioritize his young family
  • Deciding to sell a company and managing the exit process
  • Joining a VC-funded company as a key leader to help turn it around and sell it
  • Creating a defensible vertical focus as funded competitors grew and the email marketing market matured
  • Why getting a mentor or advisor is critical for young entrepreneurs to succeed

Quote from Raj Khera of 

“If you think you actually want to build a hundred million dollar company, but you like to enjoy relaxed evenings and relaxed Saturdays, I don’t think you really want a hundred million dollar company—because that doesn’t align.

“Think about what you really want. There’s no right or wrong answer. If you don’t want a $100 million company, it’s not like there’s something wrong with you. I thought it might be nice, but I wasn’t going to compromise time with my kids when they were younger.

“To me, after my first exit, time with my kids was more important. I knew that I would need to pay for that time in some way. And that way was to not build a $100 million a year company. It was a choice. Enjoy the journey, because if you’re just waiting for the destination you might just drop dead on your way.”



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Greg Head recorded this on episode on October 20, 2023 for the Practical Founders Podcast see all of the episodes.

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