Generations

I have spent decades in the startup ecosystem. Enough time to have evolved from being a beginning first-time founder to now surveying the landscape as a veteran startup CEO, board member, occasional angel investor and VC limited partner. Now, as I look around, I see distinct generations — generational waves of great people networked across the ecosystem – and that now shapes how I engage. Let us take a moment to scope out and reflect on the bigger picture, shall we?

There are people in the world who love being part of the froth of innovation at the heart of the startup ecosystem – all the potential impact and rewards that go with it. From founding teams who formulate innovative visions and blaze new trails to the investors who fuel startup companies’ development and growth to the many supporters who help bring their expertise and experience to support young companies, a whole community of people join together on a multitude of adventures. This swirling mixture of opportunities and people combine and recombine over time as many startups.

When we scope out and look at the big picture, one realizes that it is rare for a startup to remain a startup for decades. For this discussion, I am defining a startup as a company that depends on infusions of outside capital to function. Under that definition, startups that must raise capital to survive and grow will die, exit, or become self-sustainingly profitable in maybe five to fifteen years. Even surviving that long Is statistically unlikely, and it is a big push to turn that raised capital into a tangible success from concept invention to exit via acquisition or IPO.

So what does that often less than ten years per startup run mean for the careers of those in the startup ecosystem? It means that those who have been bitten by the startup bug will build careers around being involved in a series or a portfolio of startups – and those track records built across multiple startups coalesce into hard-won expertise that is deeply valued within the ecosystem. For example:

• The experience of a serial startup leader of whatever function is powerful.
  
  
• The insight of an investor who has made bets in a number of startups over time is formidable.
  
  
• The perspectives of a many-startup service provider are illuminating.
  

The bottom line is that longitudinal, startup-spanning experience matters – and those building careers in the startup ecosystem grow their valuable expertise as they grow their experience, creating an arc of professional development. There is something to be said for the experience of having seen it before, especially valuable if the sample size is greater than one. This pattern of growth over time creates what I think of as a funnel of people at different stages in their careers – from early to mid to veteran stage, such as:

• First-time founders/co-founders grow into successful serial startup CEOs
  
  
• Analysts and associates beginning their careers in venture capital who develop enough skills and experience to be invited to become partners and ultimately build the track record to become those managing partners/directors who lead the raising of a series of successful venture funds.
  
  
• Junior corporate attorneys who provide support on deals as they develop their skills and advance through the legal ranks to become senior partners in their own rights.
  
  
• Would-be angel investors who acquire the capital to become accredited investors and join an angel group to learn the ropes and grow in investing experience until ultimately they become the deal leaders others trust enough to follow.

When you are collaborating with a network of others at similar or different career stages, you start to notice that there are “generations” of players in the startup ecosystem, from serial veterans like me to those who are just getting their feet wet to everything in between. 

Now is when it gets interesting to think about. Those of us at the serial veteran end of the spectrum will not continue forever. Human beings are not immortal – and because we are human, eventually, we will “age out” and choose to shift our energy and attention to other priorities. Now, this does not happen at the same time for everyone by any means, but since I began my career in the startup ecosystem back in 2001, over twenty years ago, I have noticed that:

• Angels age out:  Those fantastic, veteran angel leaders who were so crucial to my earliest fundraising rounds have begun to age out. There comes a time when they start to say things like I am too old for making new decade-long investments when I don’t expect to be around to see them through, or I would rather focus my attention on my family/grandchildren, or I am going to retire from the hard work of due diligence and deal flow generation.
  
  
• VCs retire: Since raising the next fund means committing to another ten years as a fund manager, there often comes a time when the uber-experienced VC leaders more into “emeritus” or advisory roles for the VC firm rather than putting their names on the core of fund managers who will commit to the limited partners that they will be there for the long-haul.
  
  
• Startup CEOs evolve into other roles or retire: The energy required to sustain the intense pace of building a startup as the final, ultimately responsible leader becomes a tradeoff with other life opportunities and priorities, especially after a great exit or two. Also, applying or sharing that wealth of experience as an angel investor, startup Board member, or VC advisor starts to make more sense.

So that is the crux of it: the older generations ultimately migrate off the stage, and the next generations advance.

What can we take away and apply from these generational waves? Most important is to be aware and be intentional. More specifically, for me, that looks like:

• Be mindful of the generational pattern and broaden your investment in relationships across the ecosystem beyond just your peer group. Intentionally connect with others who are at different stages in their career path. Cultivate the trust and investment of those in the generation(s) ahead of you who are willing to invest in your career and startup. As you advance, reach out to those in the generation(s) behind you and share your knowledge, guide their development, and give them opportunities to try, learn, and experiment with guardrails and safety nets.
  
  
• See the trajectory of others’ careers because startups are a team sport, with many involved. Ideally, we work together to help each achieve their personal highest best contribution at each stage. Sometimes, that looks like answering questions and extending patience with learning to those junior legal team members, the analyst assigned to your deal, and the first-timers just entering the ecosystem. It is they who will grow into the future leaders we want enabling us to take our next steps in our own trajectories.

• Keep cultivating relationships with the next generation of investors because the more experienced generation will, at some point, move on – and, as a startup leader, you will want to have been building trust and relationships with the next generation of investors.

• Be willing to move aside to give those earlier in their journeys an opportunity and support them by providing an experienced hand-up. It is so satisfying to help them succeed by giving that vital mentorship. Be creative about the roles you can play. Help others take a chance on the up-and-comer you spotted because no one ever built a career without beginning as a first-timer. Remember, it is literally impossible for someone to become the “experienced hand” without people being willing to lean into their first-timer step, and therefore, if we believe in the strength of a veteran, remember that some of the greatest successes happen early by those who can see beyond just the surface.

Remember that, in the startup ecosystem, relationships and trust are underneath it all. Ultimately, take those shared experiences and generous desires to see others succeed and pour into your own and other generations as well. There are always significant challenges within our startup ecosystem; yet, ultimately, we need each other and are better together!