Why I Started Investing - And Started a Women's Investing Club

I used to leave all the finances and investing to Babe. When he sold some shares I wanted to hold, I decided it was time to get involved, and get other ladies involved in investing, too.

I started investing - as a woman - and thank goodness I did.

My current portfolio includes a robo-advisor, retirement accounts, savings, and stocks. But it didn't used to be like this. In fact, I didn't even know what my net worth was until Babe sold our Twilio stock without asking me first.


Way back in the day, when Twilio went public, Babe asked me my thoughts on buying Twilio shares.

“Yeah, I would buy it. I think it will be good in the long-run.”


I had no clue about stocks and didn’t directly own any myself, but I did know that many other companies and startups used Twilio as the backbone for their telephony services. That was enough for me to overcome my hesitancy on buying Twilio shares, especially for the long-run. Babe bought 10 shares of Twilio at ~$50 a pop. He said he would “never touch it” and that “it was mine” until I told him what to do with it.


We all know how that turned out. Babe, in a panic as the pandemic hit, sold all the Twilio stock at $75 a share. He told me a month later.

I freaked.

Because even though we made a profit, holding for the long-term was my preferred way to invest.

One reason why women make for better investors is because we tend to buy and hold rather than panic-sell in down markets.

If we had kept it, there’s no telling what would have happened in 5 months vs 5 years vs 50 years from now. But riding out the pandemic dip would have been my preferred decision. And in case you’re wondering how much Twilio stock is now, Google “TWLO.” 🤦🏽♀️

Still, I thank him because that frustration was the catalyst in me taking an active role in our investments. I no longer wanted to take a back seat in our investing decisions. What would happen if I were to lose Babe? Would I be prepared to handle my finances and investments? This thought left me concerned - I had to take action. Plus, I was convinced I could do a better job than him. *smirk*

In the natural splitting up of to-do lists, I had left finances up to Babe. And for all couples, that is a mistake.


I opened up a Robinhood account and spent the next month deciding what stocks to purchase. I chose to invest based on companies whose products seemed strong (mix of old and new tech) and based on my values (women-led, healthcare). For funsies, I even bought a SPAC (yep, I fell for the craze and we'll discuss SPACs in another blog post). I bought stock in ~22 different companies including AstraZeneca, Bumble, and even Twilio LOL (note: we do not endorse any stocks or give advice; this is for educational purposes only). Some give me dividends which I re-invest.


Some will be winners and some will be losers. And that's ok. Because I invest for the long-term. I don't day-trade. I sit there and let it do its thing. Picking stocks isn't for everyone, and there are other ways to invest and diversify that yield great returns with less risk.

But taking more responsibility over my financial wellness, learning to invest, and becoming a more empowered female investor weren't the only benefits that came out of this. Without even realizing, I had begun my journey into creating Penny League.

I wanted to know how other women had fallen into this same trap of knowing relatively little about investing.

To answer that, I interviewed over 50 women to understand why we seemed to know less than men about growing our wealth, why we didn't invest, and why we avoided discussing it. One that stood out? Women don't talk to other women about money and investing. We at Penny League know that when women band together, we can do powerful things.

So why don't women talk about investing?

We could go on. So ladies, let's break this taboo. The taboo was only created to keep us down. Knowing about our money is the ultimate feminist move. Because money = power. Join us - we'd love to have you.

*Disclaimer: This article is for educational and entertainment purposes only and should not be construed as investment advice. All investment strategies and investments involve risk of loss. Any reference to an investment's past or potential performance is not, and should not be construed as, a recommendation or as a guarantee of any specific outcome or profit. Consult a professional financial planner before making any decisions.

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