Evaluating Investments

Pathways for playing with public equities & private investments

Meet Sasha Hoffman, a business strategist, investor, and entrepreneur who has spent her career working with innovative technology companies to grow their global profiles, expand their revenue potential, and attract a loyal base of users by identifying complex, value-rich solutions in the areas of strategy, product development, and partnerships.

She started her career as an investment banker in the technology groups of Goldman Sachs, Barclays Capital, and Lehman Brothers, where she worked on transactions worth more than $100 billion that included several high-profile IPOs and M&A deals for clients such as Facebook, Yelp, and SanDisk. From there, she joined Plastiq – a venture-backed fintech company – as head of business development, working with credit card issuers such as American Express to enable consumers and businesses to use their credit card to pay for any purchase. She moved on from Plastiq to spearhead a new innovation division of Piaggio Group – the makers of Vespa. As Chief Operating Officer, she created new forms of transportation that utilized self-autonomous functionality to more efficiently move people and goods around modern cities. While there, she led a team that designed and launched the world’s first consumer robot called Gita that followed a human carrying their cargo. During the COVID-19 pandemic, she took on responsibility to lead consumer engagement at Uber, where she drove the company’s subscriptions business, Uber Rewards program, and third-party loyalty partnerships globally including deals with Marriott, among other global partners, managing programs that had more than 50 million users, many of which were the company’s most valuable customers. Given her background in finance and as an operator, she’s advised, consulted and invested in tech companies for the last decade, focusing primarily on B2C software, fintech, wellness and AI tech.?

While managing the demands of her various day jobs, Sasha leaned into her passion for travel and innate entrepreneurship to curate luxury travel adventures for groups of 10-100 like-minded professionals. From wellness retreats to learning how to sail and cooking intensives, she curates invite-only events for executives to connect and travel with purpose. In 2016, she was named a Global Ambassador for Women in Travel and one of the top 35 leaders under the age 35 to watch in the travel industry by Phocuswright. She has also been profiled in publications ranging from Wired to Bloomberg and has served as a keynote speaker at industry events such as WSJ Future of Everything Festival, Skift Global Forum, Collision Conference, and CES, Phocuswright.

We dive into how to evaluate investment opportunities, research sources for medium-long term public stocks, allocating part of your portfolio for more experimental investing, increasing access to private investments and how to drive goals around wealth preservation and growth.

Eve #WealthWednesday Highlight #31: Sasha Hoffman, Investor & Business Development Executive

What is your first investment?

I had just started at Lehman Brothers right before the 2008 crash, before everything went red. It was a bloodbath. I didn’t have a ton of money and I decided to take a good chunk of my signing bonus I had received a few months before everything went downhill and put it into the market. At this point, Lehman Brothers had failed, but my thinking was that there was no way they’re going to let all the banks fail, so I’m going to invest in all the other banks because something will happen there. It actually ended up being a good lesson because I ended up putting in my money and made about 10x return. I bought a lot of the financial stocks -- everything from CitiGroup to JP Morgan to Goldman -- and just put a little bit in each of them. I was really investing at the bottom of the crash and people were very scared because everything was turning very red across the board. Afterwards, we had 10 years of upswing afterwards, so I took it as a lesson that when everything is turning red, it’s actually a really good time to buy. The last couple days of the market [prior to this interview] have been very red, so I’ve been using it as another opportunity to buy. I didn’t use all of my money but I’m glad I had a thesis I saw through to the end and it ended up being money well spent.?

How/why did you get into your space?

I’ve always been good at math. During college, I majored in Accounting and Economics. Going into? investment banking was a trend from 2005 to 2008. Despite the hours, working in a bank was one of the best experiences of my life because I gained exposure to C-level executives and learned to present to them, how to read financial statements and how to think about going public or doing an acquisition.. I learned how to diligence companies and how to look at a growth curve of a good investment. I implemented a strategy of 20% active investing and 80% passive investing through wealth managers or people I trust to invest my money.?

I saved up to make my initial investments and only made investments in companies I knew something about. It was important to me to invest in products or services I understood as it made it easier for me to diligence..? Growing and preserving your wealth is essential. Start investing with what you have and develop it over time. It’s important to have a diversified set of investments. I get asked alot how much you should put into crypto and I think it’s worth at least a few percentage points of your portfolio. The wealthy have the best financial advisors and access to the best resources and deals to grow their wealth, those with under $10M of net worth usually do not. I didn’t really think that was fair. Lately, as part of the fund I'm part of, I’ve been helping women get connected to various late stage deals to help grow their pie faster without needing to pour in huge dollar amounts.

What role do you play in the wealth space and why is it important?

I work with a fund where we invest across tech, healthcare and space. I make an effort to bring more women into the tent of investing by providing access to late stage deals at smaller check sizes (Under $500k). This allows them to exit sooner and re-invest their money. I spend a lot of time speaking about financial literacy as I think it’s very important and not something we teach in school but should.? I also try to connect women to tax planners, advisors and other people who can help them optimize their money. If you are not in this space, it’s hard to know who to speak to, who the best people are and where you can go where you’ll actually be treated as an important client. If you’re just getting started, I think you should focus on 3 things: tax optimization to keep as many of your dollars as possible; proper asset allocation and diversifying your investments; giving yourself a bit of your money to start playing with so you can invest in things you’re excited about and learn by doing. My personal passion has always been travel and I curate groups for purpose driven trips. Occasionally that will be about financial wellness where we go to a fabulous destination but using our time together to talk about finances.???

What do you want others to know?

NFTs and cryptocurrencies are hyped up and top of mind for everyone right now. Many people are investing in this type of financial vehicle, but I don't think you should feel the need to if you are not comfortable just because everyone else is doing it. Unlike the stock market, it doesn’t sleep, crypto moves 24/7. You have to watch it, understand it and keep up on all the changes as the industry is evolving rapidly. If you are willing to sit down and learn about it all, then invest for yourself but if not, allocate the money you want to spend on this space to someone else who knows what they are doing. You can invest in a fund, have a money manager do it or buy a single coin like bitcoin and hold. We are in the very early days of this whole industry, it’s going to be a while so invest and be willing to sit for the next decade and you’ll eventually have some good returns.???

Who is a person or company that inspires you in the space and why?

A lot of what inspires me comes from watching different news sources. There's two main types of investing that I do. One kind involves medium-long term investments that I’m looking at 12-24 months out. I have a thesis around the sector and I’m keeping an eye on what the best 10 plays out there are. The other kind are more long-term for at least 3-5+ year plays (Private investments, etc). I read everything from The Economist to Bloomberg, to research and trend reports from McKinsey, Goldman’s GS Briefings, and Morgan Stanley research. You can go straight to their websites and sign up for their reports. I’ll pick sectors I’m really interested in and research them and reflect on which ones I think have long-term value. These reports talk about everything from inflation, to trends, to specific stocks. They have great interviews on their podcasts. I listen to research all the time while doing chores, walking my dog, on speaker in the shower; you can find time in passing to listen to at least one thing a day.

Occasionally there are more short-term investments in the markets I do for 6-12 month timeframes, but I’m not day trading. Other resources I tap into for inspiration are regularly looking through what other well known funds have purchased (you can get these alerts on your trading platform) and having Google alerts set up for all the stocks I’m actually invested in so if something really scary happens I can catch it and if they’re about to release earnings I generally know when it’s happening.?

I might be a bit more boring by approaching my investing as a sort of thesis driven by overall macro sector trends, but I tend to find that doing this consistently helps me put together a better strategy that lasts several months. That way, I don't need to actually check the market every single day, which would drive me nuts and be unmanageable.

20% of my portfolio is for play and experimentation and something I actively manage, and 80% is more passive and based on research and investigation. I have a mix of single stock picks, bonds, crypto and ETFs. If you look at research on just investing in ETFs, the indexes, or other funds, many will outweigh anything you’re going to do with single stocks. I actually research a lot of single stocks in the tech sector because it’s an area where I’ve done a lot of diligence on different companies in the space and feel like I know that sector really well but normally I wouldn't do the single stock pick game. Options are another area to make money but you have to watch it, similar to futures. On the psychedelics front, I almost created my own index. I found 10 publicly traded psychedelic companies that I really liked and am betting on for the next 5 years

Oftentimes, if you work for a publicly traded company, you’re also highly weighted in your own portfolio in that specific stock and it’s usually how part of your comp structure is being given. When I think about my overall macro portfolio, a lot of it is in investing in the market rather than in real estate or other asset classes. I’ve now moved to put a few percentage points of my portfolio into crypto, not a ton, but I’m willing to try it. A large percentage of my portfolio is in stocks and about 15% is in bonds. I also have my rainy day safety fund, which is untouched and very protected. Overall, my portfolio is a bit of a split. I might be a bit of an anomaly because I really like diligencing and the confidence I have stems from reading all these trend reports.?

What advice would you give to someone getting started?

Assuming you don't know a ton about either public market investing or private investing, I would recommend reserving a small portion of your money to just play with and give the rest to someone that you trust. Nowadays for bigger funds, you need to write a much larger track to be an LP. So, let's say you want to do some private market investing, but you don't have $5-10 million. There's a lot of new funds popping up with portfolios that want women to come in and invest. I'm a huge proponent of wanting more women investors on cap tables. Sometimes these funds will let you come in and write a check as low as $10K to be an LP. Any one of these individual funds are going through multiple raises per year, so there’s more than one opportunity that will be available any given year. One example is Portfolia.co.

I would recommend playing with both public equities you want to trade and individual private investments. You need to frame this experiment in the lens that if all the money you were experimenting with went away, it wouldn't be catastrophic. You’ll be covered in a sense as you’re taking the other 70-80% of whatever you’re comfortable with a wealth manager / family office/ personal CFO who can help you invest in things that are a lot steadier and safer.?

Start small! I think a lot of my first investments I was experimenting with were very small on the angel check size, perhaps about $10k when I started. Now, I’m able to write ones that are significantly bigger. I think things will start to make sense over time as you experiment because you will start to learn as you make mistakes in the beginning. Those initial plays I made as an angel investor didn’t go well. However, I kept talking to more companies and founders and while it does take a couple years to really get comfortable, you learn to trust your own gut. Once you get there, it’ll make sense to double down in certain areas and you’ll be in a much better place.??

Anything else we should know?

Feel free to add me on LinkedIn. You can directly send me questions if you have any or would like to invest with the fund or be introduced to tax planners or other advisors Follow me @thesashaedition on Instagram where I post some information about upcoming trips. Everything that we do is by private invite. We try to very carefully curate everyone who's coming, as well as the speakers that will be there. I like to keep this set with a small group so it's very intimate and you have an opportunity to ask questions in a safe setting. Feel free to follow me, ask questions, and when you get on the listserv, you'll also get invites on everything happening.?

#wealthwednesday #womenswealth #futureoffinance

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Have thoughts on this week’s topic or questions for me or Sasha Hoffman? Post your thoughts in the comment section. Until next week. ??

You can connect with Sasha on LINKEDIN?

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