Leadership lessons learned the hard way

COMING OUT… of triple-stealth


18 months ago, I encountered three pivotal and confidential events that had to be kept under wraps until now. Don’t worry, they’re all good!


1: Appfuel, the startup I co-founded in 2012, gained recognition in the industry, and we engaged in several acquisition conversations in early 2014 under my leadership.


2: In April 2014, Appfuel was acquired by TUNE.com, and the deal was kept confidential until the announcement of the resulting integrated product launch in July 2015.


3: I joined security startup Skyport Systems as their first non-technical founding team member in July 2014, and Skyport Systems remained highly secretive until announcing their launch in May 2015


It’s a relief to finally come out from under the cloak of secrecy and have the opportunity to share what I’ve learned during the last year and a half! In this post I share my most hard-won learnings from these unique experiences.

Throughout this period, my life accelerated from the daily startup grind (to which I had grown somewhat accustomed) to a crash course in how to handle a team, investors, and myself through extreme uncertainty and volatility.

Leadership in a small startup is an interesting beast – the CEO’s neck is on the line no matter what, and the default setting for most early startups is outright failure. What a shit deal! Fortunately, Appfuel was an exception to the rule. Here are a few highly counterintuitive leadership lessons I learned from these experiences and that I hope can be useful to you as well.


Be upfront with your team

In some of the many startups I’ve become familiar with, I notice that leadership is synonymous with painting a rosy picture for the team, regardless of reality. While CEO at Appfuel, I learned to make a point of being blunt, upfront and 100% transparent about the risk faced by the whole company throughout the journey. I saw it as a sign of respect. When things are going wrong or risk is particularly acute, the team will know it regardless of whether it is openly discussed by the leadership. It’s foolish to try to pull the wool over others’ eyes; Better to have everyone on the same page. A realistic analysis of upcoming challenges will help to motivate the team to overcome roadblocks and arm them with the most comprehensive information about what they are up against. Leaders will lose credibility and trust by coddling their team and sugarcoating bad news.


Keep an eye out for Mr. Hyde

When situations become volatile due to changes in company leadership or ownership,  opportunities often emerge to cut corners or take advantage of the situation for personal gain. When a leader is presented with these opportunities, you hope they have it in them to stay the course.  By surrounding yourself with trusted people who have strong principles, the risk of the team succumbing to these opportunities can be minimized.
Hope aside, everything you think you know about a person’s  character can change when stakes get very high; and you should be prepared for one Judas… and maybe one Brutus.   During the acquisition, I was shocked to see some (previously trustworthy) people’s behavior change when significant amounts of money, influence, or blame could be in play. For example, anyone with the ability to  stall an acquisition process or has veto power could find plausible grounds to do so, if they saw some upside to that activity. Be mindful of your own incentives and consciously force yourself to keep decisions based on the long term. Be prepared for a few surprises if the stakes get high, and be ready to move quickly and decisively if necessary.


Neglecting yourself does only harm

Be sure to look after yourself. I don’t only mean in terms of health and mental wellness, which obviously affects everyone involved.. I also mean in terms of what you negotiate for yourself in terms of role, compensation, and positioning. While we were negotiating and papering the deal at Appfuel, I would go for weeks with minimal exercise, sleep, and  healthy food, which only compounded the stress I was already feeling. I also didn’t focus nearly as much as I should have on how I would fit into everything once the acquisition was completed.
The resulting confusion dragged out the integration process and I ended up dropping down to a less active role than I would have liked after a few short months. There is no upside to self-sacrifice in terms of health or role, and when in a leadership position, you can actually cause more harm than good for everyone by neglecting yourself. Keep on top of this by being honest about what you need out of the situation and keeping your mind in peak condition through healthy living.


I hope to cover a few more points along these lines in my upcoming posts. These three discoveries were real shockers for me because they are so counter-intuitive. After seeing both sides of them I am convinced that they are critical and often overlooked.