Russ Heddleston, Co-founder & former CEO, DocSend Every owner loves their business. This makes selling their company even harder than it already is. But aside from the emotional turmoil that founders go through every exit, there are also a lot of intricacies included in the process.  In this episode of the M&A Science Podcast, Russ Heddleston, Co-founder & former CEO of DocSend, discusses the challenges of sell-side M&A. Things you will also learn in this episode: Considerations in Potentially Selling a Startup Challenges of sell-side M&A Key Factors for a Successful Exit  How to manage diligence in sell-side M&A Episode Bookmarks 00:00 Intro 04:10 Starting DocSend  06:08 Identifying the Inflection Point to sell 09:01 Selling a Startup 10:46 Considerations in Potentially Selling a Startup 14:28 Best Time for an Exit 16:00 Balancing Stakeholder Interests in an Acquisition 17:50 Relationship Management in an Acquisition 19:46 How Relationships Influence Negotiations 20:41 Relationships with Bankers 23:14 Reaching out to DropBox 26:16 Key Factors for a Successful Exit 28:04 Impact of Market Conditions on M&A 28:45 The Unknowns of Selling a Business 30:53 Post-Acquisition Challenges and Unknowns 32:34 Enhancing Preparation for Post-Close Integration 34:05 Tips for Buyers for Smoother Integration 35:18 Challenges of Sell-side M&A 37:15 Efficiently Managing Diligence 38:46 People involved from pre-LOI to Close 41:36 Post-Acquisition Team Dynamics 43:01 Evaluating Alternatives to Selling 48:28 Fundraising Strategies to Minimize Dilution 49:44 Advice for Acquirers Seeking Successful Acquisitions 51:29 Effective Strategies for Corporate Leaders to Engage with Founders 53:14 Craziest thing in M&A