Lessons and Reflections From my Experience Acquiring, Operating, and Selling a Small to Medium Sized Business


Lessons in Managing My Own Psychology

Listen to This Blog Post: Ben Horowitz, the world-renowned Venture Capitalist and co-founder of Andreesen Horowitz, said it best when he said: “By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology . . .  very few people talk about it . . . In the end, this is the most personal and important…

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The Entrepreneur and Mental Health (Part 1): My Journey

Listen to this Blog Post: Generally speaking, the average person is not fully aware of the emotional toll that entrepreneurship (or any other type of leadership, for that matter) can take. This could be due to the fact that most leaders tend to be uncomfortable with the idea of vulnerability, and instead choose to “shield” their stakeholders from the inevitable worries, doubts, and hesitations…

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The Entrepreneur and Mental Health (Part 2): My Advice to You

Listen to This Blog Post: This post is the second in a two-part blog post on leadership and mental health. Before proceeding forward, I suggest that you read Part 1 here. In the now-famous Netflix Documentary “The Last Dance”, which documented Michael Jordan and the dominant Chicago Bulls of the mid-90s, Michael Jordan said something that entrepreneurs everywhere should never forget: “Winning has a…

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Why Your Company Needs a Set of Core Values (or Why Yours May Not be Having an Impact)

Listen To This Blog Post Particularly in my early years as a CEO, I couldn’t help but roll my eyes whenever somebody suggested that I needed to codify and publish a set of core values for my company. Weren’t core values the tired, hollow, and meaningless platitudes that companies created simply because they felt they had to? Was it really that important to tell…

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Why So Many Companies Rarely Achieve Their Annual Goals

Listen to This Blog Post: Few things are as energizing as the annual goal-setting process, where the management team decides on the company’s major priorities for the coming year, usually generating a sense of enthusiasm, optimism, and confidence. Conversely, few things are as deflating as the annual review, where the same management team often retrospectively discusses how and why they missed most of the…

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Hiring Your Senior Leadership Team

Listen to This Blog Post: There is no single recipe for building a great company, nor is there a definitive formula for becoming a truly effective leader. Anything that you hear or read that suggests otherwise should be treated with a high level of skepticism. Even among the world’s most successful and admired CEOs, there exists a wide variety of personalities, strengths, weaknesses, educational…

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Migrating Your Company from On-Premise to SaaS: Part 2

This is the second post in a two-part series on navigating the transition from on-premise to SaaS. You can read Part 1 here. Listen to This Blog Post: In Part 1 of this blog, we evaluated some of the more common challenges that companies face when attempting to migrate both their product and revenue models from that of on-premise to SaaS. Though this transition is…

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Migrating Your Software Company from On-Premise to SaaS: Part 1

Listen to This Blog Post: The overwhelming majority of software companies founded over the past fifteen years or so have never known anything other than a cloud-based, single-server-multi-tenant architecture coupled with a subscription revenue model. If you’re running a software business that fits this description, then you’ll (thankfully) never need to navigate the transition that I describe below. If however you’re running a company that…

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Pricing Power: How Small Changes Can Have Big Impacts

Listen to This Blog Post: Inertia is defined as something that remains at rest or in uniform motion unless acted upon by some external force. Though software companies can fall prey to inertia in a multitude of ways, one of the most common ways in which inertia manifests is with respect to pricing. Specifically, once companies establish their prices, they often don’t revisit them, or…

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Busting the Biggest Myth About Selling Your Business

Listen to This Blog Post The entrepreneurial journey is full of innumerable risks: Your largest customers can leave at any time, and for any reason. The market may change faster than your company’s ability to adapt. Your largest supplier may decide to cut you out of the value chain and simply build your product themselves. And so on. These (and countless others) are just some…

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Considerations in Selecting Your M&A Advisor

Listen to This Blog Post: Many entrepreneurs cite the exit process as being one of the most difficult, time consuming, and emotionally trying experiences of their lives. The reality of selling a company stands in stark contrast to the manner in which it’s often portrayed in the media, where the entrepreneur allows the accountants and lawyers to sweat the details while she plans her vacation…

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What I Learned During my First (Failed) Attempt to Sell my Business

Listen to This Blog Post: “You think running a business is hard? Try selling one”. That’s what one of my mentors said to me when I approached him in 2017 with the idea of selling my business the following year. His goal wasn’t to dissuade me from pursuing an exit, but rather to open my eyes to the inevitable challenges that lay ahead if I…

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