Where's The Exit? Dennis Clerke on Timing Exits & Investor Alignment - The Venture Capital Coroner's Report

When should you sell your venture capital backed start-up? Entrepreneur Dennis Clerke joins me to discuss the start-up CEO's critical task of managing a company's path to an exit. Dennis discusses how to monitor your company's market environment and internal investor dynamics, so that you can exit at the optimal time. We also chat about promoting robust team debate while avoiding cancerous team dysfunction.

My Guest
As President of Monetization Dennis leads the content-monetization business at NetSeer, helping publishers derive greater revenue and user engagement from display and enhanced search. He also continues to work with other emerging software companies through his advisory firm DaggerBoard Advisors.

Dennis has worked with a number of software organizations on issues such as business strategy, implementation, market strategy, product development and financing. Clients include 3E Company, Alliance One, Bunkspeed, Netseer, RealGifts, Nirvanix, Captaris, SpectorSoft and TitleTrac.

Previously, he served for three years as the CEO of Alignent, a venture-backed provider of collaborative business-strategy and product-planning software, acquired by Minneapolis, MN-based Sopheon in 2007. He was a co-founder and CEO of Cardiff Software, a market-leading provider of business process management and content capture software, acquired in 2004 by Verity and now part of Autonomy.

He is on the Board of Directors/Advisors with MadCap Software, Mochila, EcoLayers, Dasko, and Pandimo. Clerke also is active with Connect, SDSIC and the University of San Diego entrepreneurial business program.

He received his MBA from the UCLA Anderson School of Business and a bachelor's degree in engineering from Boston University. In his spare time, Dennis has a passion for sailing, spending time with family and enjoying the outdoors.
Highlights & Take Home Lessons
My conversation with Dennis focused on his experience at Alignent Software. Things got challenging when it became clear to Dennis that he was either going to need a lot more equity capital or they needed to sell Alignent. The venture capital investors were split. To make matters worse, it was clear to Dennis that his industry was beginning to consolidate. Dennis talks about two of the start-up CEO's essential job:

Monitor your industry to understand when the exit window is open.
Understand the motivations and constraints of your investor syndicate

Company alignment is a great buzz phrase. Dennis shares his experience with just how important it is in reality. Debate and open dissent should be expected and is positive. Back channel dissent and unresolved conflict must be address and fast.
Resources & Links

Dennis on LinkedIn
NetSeer
DaggerBoard
Dennis' email: dclerke [at] daggerboardadvisors [dot] com

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Why a Venture Capital Podcast About Failure?
From early childhood you've always heard the saying "Learn from your mistakes." In the venture capital industry you frequently hear "Fail fast" to learn and get to the right idea. Great advice. So, for this venture capital podcast I interview venture capital backed entrepreneurs about what they learned when their start-up didn't go as planned. I hope you can learn from their valuable experience.

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