Entrepreneurial Leadership in the 2020s

TIA Ventures
3 min readFeb 15, 2021
Randy Brandoff, Leadership in the 2020s

The fundamentals of leadership — integrity, ability to delegate, learning agility, influence, decision making, etc — have probably not changed all that much in modern times. The many articles written about ‘what makes a good leader’ and the countless biographies of revered leaders remain relevant and valuable.

However, in the past year I have seen multiple examples of young start-up leaders directly addressing the fraught topics of the day with their teams, discussing how the events were impacting them personally, and then sharing their point of view externally via social media. In my career, I have been fortunate to work for numerous leaders about whom much has and will be written. And, it seems unlikely to me that any of them would have handled these moments in a similar fashion. Nor, do I believe they would have handled them as successfully as these impressive young leaders.

While leadership fundamentals may not have changed, are the expectations and demands of leadership within these entrepreneurial organizations different today? To meet these expectations and demands, are there new leadership skills and abilities evolving that in just a few years we’ll also view as fundamental (hat tip to Mr. Bezos)?

For starters, the workforce has changed. Today’s fast-growth, entrepreneurial organizations employ social media natives. They work, learn, communicate, and prioritize differently than previous generations. They have a deep understanding of and tend to prioritize the current zeitgeist over historical context. They haven’t worked through multiple economic cycles. And, they haven’t seen seismic disruptions like those that have occurred this past year alone.

With such an evolving team makeup, can today’s leaders expect their teams to keep personal and work matters separate? Ignoring the impracticality of this when the majority of folks are currently WFH, is it still practical in a world of 24x7 media? Is it possible when many need to be on Twitter, LinkedIn, Clubhouse, and more as much for professional necessity as personal desires?

When politics is seemingly omnipresent and actions, people, and even companies are perceived through red or blue lenses, when can leaders safely voice their perspective? When can employees? Is it right for the company to take a public position? When isn’t it appropriate?

As we are more conscious of our physical well being, our sleep patterns, and our mental health, is it still frowned upon for a leader to address their own emotions and mental state? Can a leader make a deeper connection and demonstrate strength by showing weakness? This same changed audience is drawn to authenticity and their BS detectors are sharp. Whatever approach today’s entrepreneurial leader takes, they have to believe in it and commit to it or it’ll backfire.

As investors, we focus on things like product/market fit, growth rates, capital efficiency, customer satisfaction, and traditional methods of leadership communication and company culture.

As leaders, you’re under tremendous pressure to scale your product, team, brand, and topline metrics. To iterate, measure, and find what is repeatable. To manage investors and stay ahead of capitalization requirements.

But, all parties need to begin focusing immediately on the evolved requirements and expectations of entrepreneurial leadership. It’s time to identify and appreciate these important new leadership skills. To voice and agree upon some new ground rules. Because while the details on the future of work are debatable, it’s a near certainty that the expectations and demands of entrepreneurial leadership are never going back to the way things were…

-Randy Brandoff, TIA Ventures

Twitter: @TIA_Ventures




TIA Ventures

TIA Ventures is a seed-stage venture capital fund that partners with companies building emotional and visceral connections with their consumers.