Old People Know Stuff

Danielle Gillespie
3 min readOct 4, 2021


No matter how old you are, your startup needs someone with experience to help you navigate.

When I was a newly minted software engineer in my early 20s, I thought anyone over the age of 35 was OLD. Like really old. I was petulant, impatient, always on the move and had absolutely no bedside manner (I still have trouble with that one). I got away with a lot because I was very good at my job, but in retrospect, I would probably not recommend my approach to anyone who would like to advance their career.

In one of my earliest roles, I sat across from a super interesting guy who was probably in his early 40s (aka OLD). He was on contract to help push a product over the finish line and was not only an extraordinary engineer but also an extraordinary human. Without ever once blatantly telling me I needed to tone it down, he helped me understand that I really needed to tone it down. I don’t know what kind of wizardry was at play but the lightbulb finally went on; I needed the experience and maturity that comes with time and reps if I were to ever become a great engineer, team member and/or leader.

It can be a frustrating message but guess what? There are ways to accelerate experience and maturity if you’re willing to learn and cooperate.

The Cheat Code

For less experienced founders who are open-minded, it can be extremely valuable to work alongside more experienced professionals; a strategy that can ultimately help founders take more efficient strides toward an end goal.

How do you introduce experience into the equation without disrupting balance? Use mentors, advisors and dedicated professional executive-as-a-service (EaaS) providers to augment your team.

  1. Mentors: I liken mentors to therapists. They usually have no skin in the game so you can be completely honest. They can help you talk through whatever road block you’re facing, help you change your mindset and work through tough decisions.
  2. Advisors: Your board of advisors should be intentionally selected to fill gaps in your team’s experience and capabilities. An advisor is regularly updated and consulted in their area of expertise to help move the business toward its objectives.
  3. EaaS: AKA your accountability partner (sometimes called executive coach). This is someone who is usually hired by contract to help you set goals, prioritize and make sense of all the inputs. Your accountability partner is someone with whom you have a formal relationship and a standing meeting once a week, or every other week, for a couple of hours. You talk about what you did last week and what you’re doing next week. You should feel energized for the tasks ahead even if you’ve come off a bad week. You should gain confidence in your actions and let go of any perceived failures from the previous week.

There can be some overlap between mentors and advisors but the main difference is that you will likely have an informal relationship with a mentor. You might meet with them once a month, or have ad hoc phone calls/periodic text or email for random questions and advice.

An advisor has a slightly more formal role; advisors show up as members of your team and oftentimes are exchanging their time for a small number of options.

In Practice

One of the best things I ever did as a startup founder (and the single piece of advice I routinely give): I found an accountability partner. It was someone I met with once a week for 2 hours. I looked forward to the session. Some weeks I crushed it, others were dismal. I was always energized by the end of the meeting. To this day, I miss those weekly sessions.

Leaders and founders are expected to have all the answers. And most leaders have trouble asking for help. Having an impartial third party or a fresh set of eyes on your challenges can really help with perspective and prioritization.

Even on a small budget it’s possible to find someone who can meet you where are and help you get to where you want to go.



Danielle Gillespie

Defining the intersection between technology and human connection (I also help entrepreneurs build rock solid tech products: daniellegillespie.net)