Entrepreneurship

Posts from David DeWolf on entrepreneurship, his experience as an angel investor and board member, and important lessons he has learned that fellow entrepreneurs should heed.

Why Diversity Builds Stronger Leaders: The Evolving Leader, Episode 9
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For this episode of The Evolving Leader, Heather Combs and I talk about how diversity of thought, experience, and opinion ultimately builds stronger leaders, leadership teams, and companies. Heather served…

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Making and Managing Acquisitions - The Evolving Leader Episode 8
Making & Managing Acquisitions: The Evolving Leader, Episode 8
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Dan Henderson joins me for this episode of The Evolving Leader to talk about acquisitions, an important, potentially vital tool for growth that the evolving leader must use judiciously. Dan…

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Leadership + Emotional Intelligence: The Evolving Leader, Episode 4
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Emotional intelligence is often overlooked when we’re thinking of the most important leadership intangibles. Far too frequently, leadership is mistaken for charisma, or even popularity or social ease. For this…

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Leadership & The Stages of Growth, Continued: The Evolving Leader, Episode 3
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Bobby Christian joins us again for episode 3 of The Evolving Leader to continue our discussion on how and why your leadership focus and capabilities must adapt as your company…

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Leadership & the Stages of Growth: The Evolving Leader, Episode 2
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Back in 2012, I wrote a blog post called The Stages of Entrepreneurial Growth. It was a short post that was almost entirely comprised of an email that Bobby Christian,…

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Why Are We Here?: The Evolving Leader, Episode 1
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For the first episode of my new series, The Evolving Leader, I talked with host Will Sherlin about why I felt compelled to start the series. The short version is…

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The Top 4 Lessons I’ve Learned from Acquisitions
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I’ve been involved in a fair share of acquisitions over the years. We recently completed 3 in a span of 8 months, and our first acquisition dates back to 2009.…

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The Top 3 Lessons I’ve Learned Raising Venture Capital
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On March 9th, 2020, just as the global pandemic began to surge and public markets became unstable, 3Pillar closed a strategic investment. This investment was the culmination of a long…

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In the Market for VC Funding? Start Here.
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I’ve had the good fortune to lead 3Pillar through a few significant investment rounds over the last 10+ years. Investors in our business have included leading venture capital and private…

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How We Built 3Pillar Into a $100MM+ Company
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I founded 3Pillar Global, or Three Pillar Software as it was originally called, in 2006. I was the lone employee when I signed the paperwork incorporating the company, and that…

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