From Founder to Acquisition: A Journey to Microsoft - Jon Gilman - Built to Finish - Episode # 012

Jon Gilman, founder and former CEO of Clear Software, discusses his journey from founding his company to its acquisition by Microsoft in 2021. He elaborates on the challenges he faced, including the intense stress of managing and eventually selling his startup. Jon emphasizes the importance of having multiple potential buyers at the negotiation table and recounts the bittersweet moments when deals fell through. He highlights the transformation and stability his team experienced post-acquisition, the operations of Microsoft's Power Platform, and the profound support from Microsoft that allowed him to regain work-life balance. Jon also shares advice for startup founders about persistence and mental health, stressing the importance of not giving up and employing healthier stress management techniques. The interview concludes with Jon encouraging current entrepreneurs to persevere through their struggles, promising that light can emerge at the end of the tunnel.Takeaways:Don't Give Up: Persistence is essential for success as a founder. Even during the darkest times, it's crucial to keep pushing forward if you believe in your vision and its value to the market.Take Care of Mental Health: Entrepreneurship can be a long and strenuous journey. Finding healthy ways to manage stress, such as meditation or physical hobbies, is critical for long-term sustainability and well-being.Engage Multiple Players at the Table: When considering selling your company, having multiple interested parties can create a competitive environment that maximizes the potential outcome for everyone involved.Consider Investment Bankers: While it is possible to handle acquisition processes on your own, going through a structured process with an investment banking firm can provide valuable expertise and potentially lead to better deals.Prepackaged Solutions for Enterprises: Offering prepackaged solutions to larger enterprises can simplify their decision-making process and streamline the adoption of new technologies, which can drive faster sales and deployment.Competitive Process to Increase Valuation: By fostering a competitive environment among potential acquirers, you can significantly increase your company's valuation and chances of a successful exit.Transparency with Your Team: Maintaining transparency with your team, especially about major processes like acquisitions, builds trust and keeps everyone aligned towards common goals. However, consider what information might be too stressful or unnecessary for everyone to know.Quote of the Show:“If you really believe in what you’re doing and that it provides value to your buyer, you just got to stick with it.” Links:LinkedIn: https://www.linkedin.com/in/jongilman88/ Website: https://www.microsoft.com/en-us/ Ways to Tune In:Spotify: https://open.spotify.com/show/1ghmiiaRwVtQ9kqqqvmVQY Apple Podcasts: https://podcasts.apple.com/us/podcast/built-to-finish/id1781753842 Amazon Music: https://music.amazon.com/podcasts/665cacbf-79ed-4745-8856-1d8465943c65 Podchaser: https://www.podchaser.com/podcasts/built-to-finish-5907037 YouTube: https://youtu.be/FUO9eQflH3A 

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