Selling Insided to Gainsight: Insights to Exit, Robin van Lieshout on Building and Selling a Software Giant

The Big Exit Show

In today's episode, we're delving into the remarkable entrepreneurial journey of Robin van Lieshout, the founder who recently led his company Insided to a monumental acquisition by Gainsight.

In this intimate conversation, Robin opens up about the highs and lows that come with building a successful business from its online consumer electronics origins to a community software leader netting 100 million ARR in 2022. Listen in as he shares the ups and downs of partnering with a friend, the emotional impact of downsizing his team, and the strategic moves that substantially increased his company's valuation.

We're also tackling the personal side of selling a business. Robin reflects on his quest for meaning and purpose post-acquisition, the significance of creating a network of peers for support, and the influence of company culture on a successful team dynamic. Get an inside look at what it takes to navigate the challenges of international expansion and hear Robin's candid take on the decision-making process that eventually led to Gainsight's purchase offer.

Learn about the considerations that outweighed even high valuation term sheets, and discover why Robin made the tough choice to prioritize stability and strategic alignment over greater financial incentives. Robin also imparts wisdom on the value of external perspectives and the role they played in his company's pivotal moments.

So, tune in as we explore these insights and more with our exceptional guest, Robin van Lieshout, on this episode of The Big Exit Show. Whether you're a founder, investor, or merely intrigued by the art of the exit, today's conversation is sure to enlighten. Stay with us, as we uncover the complexity and victories within the ultimate entrepreneur's rite of passage—the big exit.

• 06:41 Starting a company with close friends.
• 11:21 Invested in culture and team dynamics from start.
• 16:17 Changed my perspective on board meetings positively.
• 21:19 Balancing ambition with honesty and realism is crucial.
• 28:42 Struggles as a CEO, seeking external perspective.
• 32:39 Organization crashed due to selling to many segments.
• 39:08 Flew to London for 20-minute vision presentation.
• 46:55 Disagreement over currency reporting, causing nerve-wracking delay.
• 52:04 Considering selling company to unknown brand name.
• 57:50 Assumptions about customer base and revenue growth.
• 01:02:30 Quiet office celebration for pending acquisition announcement.
• 01:07:42 Considering future roles and potential time off.

Getting to know Robin van Lieshout:
Robin is an Entrepreneur, Investor, Strategist and Community Builder. He founded and sold two companies, most recently inSided, a SaaS platform for technology companies to build their own Community. He raised $7M in funding, scaled to 100+ employees worldwide and eventually sold to San Francisco based Customer Success leader Gainsight.
Robin currently acts as the Chief Strategy Officer at Gainsight, where he is responsible for several product lines, new market development, long term corporate strategy and M&A. He recently did his first $50M+ acquisition and has the experience of being on both sides of the table. In his free time he is an advisor and investor in many startups, large VC/PE funds and in family time.

You could find Robin's book: Customer communities here.

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Catch you on the next episode for more incredible exit stories!