If You Are An “Older” Person How Do You Find Your Way Into Startups?

Often I have a cup of coffee or conversation with an “older” person looking to find a new path for their career. By older person, I mean a person over the age of 45. I suppose one of the reasons they want to have coffee is because they perceive that I have successfully navigated that road.

Well, sort of.  I still have some work to do. I will tell you the road is extremely rocky and you have to have capital in the bank, and the stomach for it.

If you want a job with a startup, the first thing to do is check venture capital firm websites.  A good VC will list job opportunities in the startups they are invested in.  (Another thing on my “to do” list)  At the very least, you can see the companies they are invested in and go to their website where job openings should be listed. Even if it’s a Silicon Valley VC, not all the jobs will be in California forcing you to move. Interestingly, a lot of top-flight startups have their marketing departments in Chicago.

“Give before you get”.  Another way in is to mentor.  You don’t get paid to mentor.  Don’t go into mentoring with the idea that you will build a “pay for” consulting business.  There are plenty of guidelines around mentoring that you can find in other blog posts.  Contact a local co-workspace, accelerator, or an organization like The Junto Institute and talk to them about mentoring.  I couldn’t begin to total the hours I have donated.

You can serve as an independent member of a board of directors.  But, you better have subject matter expertise.  You also aren’t going to get a lot of payment or equity.  It’s a labor of love.

I’d ignore most of the qualification language in job postings unless it’s technical.  If you like what the startup is doing and think you can fill the position, go for it.  However, if you have always dreamed of being in operations and never have done it, don’t apply for an operations job.

Here are a few thoughts that someone has to accept before they walk the road.

• Despite all the glamour you read about startups, it’s a really hard job. I think we tend to focus on reading about the home runs. People that are embroiled in the struggle don’t talk about it for a lot of reasons. The primary one is time. They don’t have the time to write down the internal pain and consternation they are going through.
• Startups are always resource constrained.  There is never enough money or talent.  If you are coming from a corporate environment, you might think you are used to that but you haven’t experienced what they experience in a startup.
• The difference in hours.  A lot of startups don’t get humming until 10 am.  I was always used to getting up a 5 am and being at work by 6:30 am.  I can walk into most co-work spaces or startup offices at 7-8am and no one is there. Because we can work remotely (thanks Deskpass) and are always connected a lot of work happens out of the office.
• The clothing differences are easy to get used to.
• You might have to start in a role that doesn’t suit your reputation or credentials.  If you are into titles startups aren’t for you.
• The roles inside a company are squishy.  People wear a lot of hats and just “get shit done”.  Coming from a line and staff organization and getting used to it can be upsetting.  It’s also freeing.
• Fear.  Dealing with the constant pain of feeling like you might go out of business.  This is a motivator but handled the wrong way it’s an impediment.
• Risk.  You have to have a high tolerance for risk.  If you are seeking stability, don’t work for a startup.
• Pay is a lot less. You are working for the equity.  Every dollar that is paid to employees in salary increases the burn rate and constrains the startup.

Figuring out the stage the startup is in makes a difference.  Do research and be honest with yourself about which stage you want to enter at.  Crunchbase usually shows the funding rounds and investors.  Networking into a startup via an investor is a good way to get to know them.  I can hook people up with founding teams that are on their 3rd to 10th employee and on their first round of funding.  I also know startups that are later in the process.  The above list applies to either of them.  However, a Series A, B, C, D startup have already started to build their corporate culture.  That being said, a lot of the skills older people have acquired in their careers are directly applicable to startups.

• A lot of times, startups haven’t done things like budgeting correctly.
• They have trouble building processes
• They don’t allocate resources correctly to align with the goals they are pursuing.
• They lose focus and chase shiny objects.
• Often, they don’t understand what it takes to bring a product from A to B.
• They don’t have networks into larger organizations.
• They don’t understand how to sell them.
• They way overestimate the positives without looking at the downside.

Certainly, investors help with these problems at different stages.  But, it helps to have someone there day to day that can keep the company between the lane lines.  It is totally possible for older people to join the startup world. They just have to be realistic about what that world is like, and realistic about themselves to understand if they can fit themselves into that world.