Career Advice For Women: Blaze Your Own Path Instead!

For the past five years in a row I’ve spent time interviewing with companies during the 4th quarter in preparation for the new year. It’s always good to seek new opportunities and have backup plans, even if you never use them.

Sometimes, the interviews turn into fun consulting roles where I spend anywhere from 10 – 25 hours a week helping startups build their online presence. Never have the interviews turned into full-time roles because I just can’t convince myself to go back to work full-time.

I start getting depressed thinking about having to commute, taking orders from people, wasting time in meetings, faking enthusiasm, kissing up, etc. Seriously, I don’t understand how people can survive the daily rush hour commute! Building someone else’s dream while getting 1/30th the amount of equity is tough for me to swallow.

What I do enjoy is meeting new people and hearing their stories about how they plan to change the world. At the very worst, I’ll have made some new connections in the SF Bay Area who might utilize my corporate consulting services or be potential new business partners. And almost always, I’ll have a new story to share with you.

Here’s a recent incident I will never forget. What I experienced revealed an ugly side of startup culture and what some men really think of women behind closed doors. 

A Boulder On Your Shoulder

The second round of my interviews with a life insurance startup involved giving a presentation about what I’d do for them during my first 100 days. I whipped up a 10-page presentation from the consulting pitch material I already had while watching the Warriors blow out the Thunder the night before. The presentation was concise and to the point.

When I got to their offices, the Head of Brand was in the conference room waiting for me. He was a new hire whose résumé showed the typical job change every 1-3 years.

While waiting for four other people to show up, I asked him whether or not he also had to give a presentation and share all his secrets before getting hired. He said that he did. Then I asked him how long his presentation was given I had a suspicion mine might be too short. I had been out of the work force for so long that I forgot having a lot of fluff makes a difference.

The Head of Brand told me his presentation was 54 pages! Holy crap! It was a harbinger for a tough session ahead.

The CEO, two co-founders, and the Head of Growth finally showed up at 1:08pm; the meeting was supposed to start at 1pm. The head recruiter also walked in behind them and told me in a nasty voice, “You’re late,” when I had actually arrived at 12:55pm.

She had texted me at 10pm the night before requesting me to arrive at 12:45pm instead. We had agreed on a 1pm time slot after a lot of back and forth already. Was she seriously trying to change it on me again at the last minute? I ignored her text. Have some boundaries please.

I was looking forward to having one of the co-founders in the meeting, a man I’ll call Amit, because he had a very skeptical line of questioning when I met him 1X1 during my first visit. Think of Amit as a guy with an automatic machine gun gleefully firing endless rounds at a helpless puppy just for the fun of it. Without a machine gun, he would run away like a coward if you decided to confront him with your fist.

Amit had a chip on his shoulder because he was in his early 30s and spent six years trying to get his PhD. He finally gave up for a second time in 2012 and started some random company I’ll call Pewko, which he describes on LinkedIn as a company “where you can have meaningful interactions with your friends online.” It’s obvious Pewko vomitted all over itself and didn’t go anywhere.

Then in January 2013, Amit met up with his other co-founders and started this life insurance startup I was interviewing for. So far, so good. Although, it will be years before there’s any meaningful exit for them, if any at all, since most startups don’t have lucrative outcomes. If you’re in your 30s, went to Cal or Stanford, and haven’t hit it big in the Bay Area yet, it’s understandable to feel inadequate since there are so many success stories here.

I was one minute into my presentation when Amit started riddling me with questions again. It was hilarious! My second slide was entitled, “The First 30 Days,” and one of the bullet points mentioned me sitting down with everybody to understand what type of messaging they wanted to portray to the world. It’s good business practice to understand first, then execute.

Amit started asking questions such as,

“How do you plan to scale the content to grow exponentially?”

“Tell me how you are going to get this done?”

“What are the numbers behind your proposal?”

I gave him some answers and told him more details were to come in the following slides. He didn’t seem too pleased. He is the type of person who loves to talk in meetings just to hear himself speak. I suspect he also has ADD.

Then I got to a slide that highlighted an influencer I proposed to hire to help promote their startup. The influencer is a woman in the fitness/yoga/pilates space. My idea was to cross sell using influencers with healthy lifestyles who can promote some of the financial benefits of being healthy. It’s a smart way to capture related topics and rank well online.

Amit, of course, chimed in with another five questions. He was not convinced by my online strategy that has worked for the past eight years even though during that time he was still trying to pass his introductory PhD classes.

This is when the CEO, whom I’ll call Raj, suddenly spoke up. (Note: Raj had walked in and out of the conference room three times by this point to take calls)

He said, “I HATE women! I don’t want female customers. They live too long, which means they pay less premiums for life insurance. They also take forever to sign up. I’ve only got a finite amount of sales people and can’t be bothered trying to hold each and every woman’s hand.“

I was in shock. This life insurance startup’s whole value proposition was all about being able to offer lower life insurance premiums for those who are more health conscious due to a proprietary mortality table they’ve been building.

Now the CEO is telling me he doesn’t want female customers because their returns aren’t high enough to bother?! I felt like I was in an episode of Silicon Valley on HBO.

A normal person who respects women would say something like this instead, “Women aren’t our target customers at the moment due to X, Y, Z” or just keep silent instead of saying how much he hates women and then go on a long rant.

I looked at Amit, who was smiling gleefully because he could tell I was finally feeling uncomfortable. He was that pimply kid with wide eyes squishing ants!

Then I looked around the room and realized nobody flinched at Raj’s outburst because all five of my interviewers were men.

So THIS is why some women complain about a lack of diversity in the work place. The three main co-founders were Indian men. The Head of Growth was a Chinese guy. The Head of Brand was a Middle Eastern guy. Good luck being a woman at this startup!

The saddest thing is that there are female employees at this startup who probably have no idea about what the founders truly think of them.

The overly enthusiastic head of recruiting is a woman who believes her CEO views women equally. As a result, she has no problem trying to recruit other women for the job.

I also spoke to one of their female employees who is two years out of school. She said she works past 8pm all the time and loves the opportunity. Little does she know that there’s a thick glass ceiling waiting for her in several years due to the management makeup.

Companies give incredible lip service towards hiring women. The reality is that everybody is biased for people who look and talk like them. It is no coincidence all the founders at this company are Indian. And it is not a coincidence all their senior management are men too.

Here in Silicon Valley, I’ve noticed that once a computer science guy comes to power, the workplace dynamic gets quirky because either the guy was socially awkward in school who feared talking to women, or has some kind of chip on his shoulder because no women talked to him growing up. It’s like that loser in high school who can’t wait to show up to his 10 year high school reunion in a Lamborghini and tell everybody what a success he is.

Blaze Your Own Trail Women!

I think about women’s issues a lot because I have a sister who is a single mom. I sometimes worry about how she plans to make ends meet living in expensive NYC. She spent eight years out of the workforce to raise her son. And now, she’s trying to catch up to make it as an illustrator, author, and freelancer.

I also have a wife who went through a difficult period back in 2013. She worked like a loyal juggernaut for eight years at her firm only to be passed up for a promotion when her firm promoted two men a couple years her junior instead. It was total bullshit, especially since one of the promotees left the very next year.

I also felt like a failure because I didn’t properly coach my wife to totally get what she deserves. She’s too nice to ask for what she wants, and naively believed that good work was all that’s needed to ascend.

The great thing is that we finally negotiated a nice severance package for her in late 2014 to be free with me. Part of the negotiation was receiving her full salary for the last four months while she only had to work two days a week. She also received a nice lump sum severance and got hired back as a part-time consultant 10 months later for 50% higher pay!

I also believe that one day I might have a daughter. Like every father, I want my daughter to have all the opportunities in the world. I fear how other men will treat her personally and professionally. I’m afraid she won’t fulfill her dreams due to some sexist management team who secretly looks down on females. But if she falls, I will always be there for her.

Finally, many of you are women who’ve shared with me your struggles. Please continue to do so. I firmly believe the stress from work is one of the main reasons why people are so unhappy with their lives. There’s too much backstabbing, political jockeying, and cronyism to make work a long-term happy place to be. Even harder are those women who are trying to balance their careers and motherhood.

I can tell you how awesome it is to be your own boss. But you won’t really know how awesome it truly is until you give it a go yourself. If you don’t want to go at it alone, find some co-founders who share your same traits and build something together. The entrepreneur hurdle has never been lower thanks to technology. If you fail, you can always get another job.

If you are a woman, be wary of a company with a homogenous management team. Group think is inevitable when everybody comes from the same background. “Locker room” talk is embedded in many men’s DNA. I’ve played sports all my life and have sat in on all-men meetings plenty of times before in my finance career, things are not always what they seem from the outside.

Career life is much easier if you can find a mentor who shares your same interests. More often than not it’s a person who looks like you. If you can’t find your champion, move on.

I’ll leave you with a great quote I saw online:

“Job you love? GOOD. Supplement it with a side business.

Job you hate? GOOD. Pays bills while you start a business.

No job? GOOD. More time to start a business!”

Recommendation If You Want To Move On

Negotiate A Severance: If you want to leave a job you no longer enjoy, I recommend you negotiate a severance instead of quit. If you negotiate a severance like I did back in 2012, you not only get a severance check, but potentially subsidized healthcare, deferred compensation, and worker training.

When you get laid off, you’re also eligible for up to roughly 27 weeks of unemployment benefits. Having a financial runway is huge during your transition period.

Conversely, if you quit your job you get nothing. Check out, How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye.

It’s the only book that teaches you how to negotiate a severance. In addition, it was recently updated and expanded thanks to tremendous reader feedback and successful case studies.

Recommendation To Build Wealth

Manage Your Money In One Place: Sign up for Personal Capital, the web’s #1 free wealth management tool to get a better handle on your finances. You can use Personal Capital to help monitor illegal use of your credit cards and other accounts with their tracking software.

In addition to better money oversight, run your investments through their award-winning Investment Checkup tool to see exactly how much you are paying in fees. I was paying $1,700 a year in fees I had no idea I was paying.

After you link all your accounts, use their Retirement Planning calculator that pulls your real data to give you as pure an estimation of your financial future as possible using Monte Carlo simulation algorithms. Definitely run your numbers to see how you’re doing. I’ve been using Personal Capital since 2012 and have seen my net worth skyrocket during this time thanks to better money management.

Updated for 2020 and beyond.