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Shomik Ghosh: All Things Enterprise Software Investing


Shomik Ghosh is a principal at Boldstart VC by day and resident Enterprise Software savant by night. Shomik’s job at Boldstart VC is to find and become Day One partners with passionate, technical Enterprise Founders. This means Shomik spends all his time thinking, analyzing, and valuing enterprise software businesses.

This conversation is a HUGE asset as we navigate the enterprise software investing landscape over the next 5-10 years.

Our conversation dives deep into the world of Enterprise Software. More importantly, Shomik takes us on a journey through his slide deck “Framework For Evaluating Enterprise Software Companies”. This is one of those podcasts you’ll want to listen to twice. Shomik breaks down competitive advantages, favorite stacks within Enterprise Software, as well as rebuking common myths investors believe about the space.

Here are the show-notes:

  • [0:00] Who is Shomik Ghosh?
  • [6:00] The Importance of Founders
  • [10:00] Differences between Investing in the Private Markets and Public Markets
  • [16:00] 6 Steps for Evaluating Enterprise Software Companies
  • [20:00] What is Alignment of Cost Structures?
  • [27:00] The Importance of Switching Costs
  • [45:00] Distribution in Software Companies
  • [53:00] Security as Enterprise Software
  • [1:03:00] Exciting Areas in the Enterprise Software Industry
  • [1:13:00] More from Shomik and Closing Questions

If you like what you heard from Shomik Ghosh, check him out on Twitter @shomikghosh21

This episode is brought to you by TIKR. Join the free beta today at TIKR.com/hive. They’re constantly releasing new updates that make the platform better including a new Business Owner Mode that hides share count, market cap, and enterprise value. I couldn’t be more excited to partner with TIKR.

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Brandon Beylo

Senior Partner at MO, PM at Foundation Capital, lead value investor, ValueHive podcast host, and a tennis nut. https://www.x.com/marketplunger1

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