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 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

Value Investor

Brandon has been a professional investor focusing on value for over 13 years, spending his time in small to micro-cap companies, spin-offs, SPACs, and deep value liquidation situations. Over time, he’s developed a deeper understanding for what deep-value investing actually means, and refined his philosophy to include any business trading at a wild discount to what he thinks its worth in 3-5 years.

Brandon has a tenacious passion for investing, broad-based learning, and business. He previously worked for several leading investment firms before joining the team at Macro Ops. He lives by the famous Munger mantra of trying to get a little smarter each day.


Investing & Personal Finance

AK is the founder of Macro Ops and the host of Fallible.

He started out in corporate economics for a Fortune 50 company before moving to a long/short equity investment firm.

With Macro Ops focused primarily on institutional clients, AK moved to servicing new investors just starting their journey. He takes the professional research and education produced at Macro Ops and breaks it down for beginners. The goal is to help clients find the best solution for their investing needs through effective education.

Tyler Kling

Volatility & Options Trader

Former trade desk manager at $100+ million family office where he oversaw multiple traders and helped develop cutting edge quantitative strategies in the derivatives market.

He worked as a consultant to the family office’s in-house fund of funds in the areas of portfolio manager evaluation and capital allocation.

Certified in Quantitative Finance from the Fitch Learning Center in London, England where he studied under famous quants such as Paul Wilmott.

Alex Barrow

Macro Trader

Founder and head macro trader at Macro Ops. Alex joined the US Marine Corps on his 18th birthday just one month after the 9/11 terrorist attacks. He subsequently spent a decade in the military. Serving in various capacities from scout sniper to interrogator and counterintelligence specialist. Following his military service, he worked as a contract intelligence professional for a number of US agencies (from the DIA to FBI) with a focus on counterintelligence and terrorist financing. He also spent time consulting for a tech company that specialized in building analytic software for finance and intelligence analysis.

After leaving the field of intelligence he went to work at a global macro hedge fund. He’s been professionally involved in markets since 2005, has consulted with a number of the leading names in the hedge fund space, and now manages his own family office while running Macro Ops. He’s published over 300 white papers on complex financial and macroeconomic topics, writes regularly about investment/market trends, and frequently speaks at conferences on trading and investing.

Macro Ops is a market research firm geared toward professional and experienced retail traders and investors. Macro Ops’ research has been featured in Forbes, Marketwatch, Business Insider, and Real Vision as well as a number of other leading publications.

You can find out more about Alex on his LinkedIn account here and also find him on Twitter where he frequently shares his market research.