Angel Investor & Fund Manager: Jenny Fielding

Jenny Fielding is the rockstar, co-founder and managing partner of The Fund, a pre-seed fund supported by a community of brilliant founders and operators. Jenny previously spent 7.5 years as managing director at Techstars and also founded two companies herself. Jenny's unwavering passion to help startup founders succeed is obvious from the moment you speak to her!

Highlights:

• Jenny got into angel investing by first mentoring founders & building a network through that
• She helps founders with fundraising strategies
• Jenny is co-founder and managing partner at The Fund

What inspired you to start angel investing?

I was a founder, and by the time I sold my second company, I had made a lot of mistakes running the business. This led me to meeting with other founders, trying to impart any types of learnings that I had so they didn't make the same stupid mistakes I did.

Through that, I got to meet a lot of founders and understand their businesses. So I was helping out quite a bit, and I thought, “well, if you're helping, you might as well get a little upside”. Basically I started by putting a small amount of money in some companies.

At the time, I didn't consider myself a very active angel because I was just quietly writing small $10-$20k checks into companies, but it all happened very organically, through mentoring and helping out.

Are you a generalist or do you have a specific expertise you help founders with?

I think when I was running my company, I was more of a generalist. It was everything from hiring, to setting up operations, to scaling. But now the thing I'm most known for is helping founders fundraise.

I fundraise myself, and I've helped around 500 founders go through fundraising. I've learned a lot of tips and tricks and things that oftentimes can be helpful, and have built a massive network of investors. The thing that people mostly come to me for these days is around fundraising strategy.

What is the most important aspect of fundraising?

It comes down to one thing, and that’s being organized. I built a whole PowerPoint deck on how to create a really good fundraising process through an investor pipeline doc. But essentially it boils down to running a very organized, efficient fundraising process.

I've spent a lot of time helping founders understand that, get organized, and then have a strategy to really build momentum, because fundraising is all about building that excitement and momentum in the round.

Any deal breakers when it comes to how founders do their pitches?

What I tell founders is that you have to approach every meeting as a bespoke situation because everyone likes to be pitched a different way. It's your job as the founder to decode what that is. In the same way that you’d go out with a bunch of friends and meet new people and you're going to act in a different way, you kind of have to feel them out and understand what resonates with them. I don’t like it when founders just want to share their deck and talk at you for 20 minutes straight.

Although it’s not how I want to be pitched, it could be how some people want to be pitched. So I think the most important thing is to understand in the first few minutes of the conversation what's going to work for this person in the same way you would having dinner with a friend or someone else.

That's what's hard about it, but it's also what's fun about it. It's really about decoding the other person and what makes them tick. Personally, I like a two to three minute summary and then to go into more of a discussion. But again, everyone likes it differently, so it's for the founder to understand what's going to resonate with the investor.

Is the downturn a good time to be investing?

Well, the data shows that downturns are the best time to invest. So if you look at the data, companies like Uber and Airbnb were created in that cycle. I think if you're not investing in the cycle you're missing out on some of the best vintages and that's probably a mistake.

We are active through up and down cycles and we're just as active now as we were last year. So I think it's a great time to be a founder. If you're raising early stage there's still a lot of cash and excitement. I think if you have to raise a Series B or a growth round it's tricky, but for pre-seeds and seeds, the market is still pretty healthy, especially around certain verticals.

What verticals do you invest in with The Fund?

We're generalists at heart but we invest directionally across three verticals: money, health and work. What we call the table stakes economy, so we do a lot in fintech and payments, and a little bit in web3. Those are the areas of focus but every once in a while we see something we love that's outside of that and we’ll make exceptions.

What's your take on AI?

That's in our third bucket. We've been investing in automation for quite a long time and automation powers most vertical SaaS, which we like to invest in as well. We're not running after any chatGPT right now, but I'm excited about that space. We've always been keen investors in AI so it's great just to have new tools out there.

How many people run The Fund with you?

I have one co-founder, Scott Hartley. He's fantastic. Then we have about 30 venture partners and  founders and operators. All are investors in our fund and they help us source, do diligence and invest in companies and in geographies around the world. So we have people in Africa and people in Austin, Texas. We are all over the place and working towards building a global firm.

Do you do any outbound?

We don't do any outbound. We mostly meet founders through our community. So we have 500 founders and operators that are all part of The Fund community. They're all people that have invested in us and they're our eyes and ears on the ground. So I think what's unique about us is that all of our deal flow comes from those people and we don't do outbound, which is pretty unusual.

I feel like most VCs kind of pride themselves on having a thesis and going after and finding the best companies. Ours is the opposite in which we think founders and operators are seeing the best companies and so they're sending them to us early on for us to get to know them.

Your top advice for aspiring angel investors and fund managers?

My advice is that it's a long game and that most people don't know whether or not they're good at it for ten years. You have to be committed to the asset class if you want to be investing and really enjoy the craft of investing, because it's not the type of thing you can just kind of try here and there.

You need to work at it, and you need to have a diversified portfolio, and it really is about the power law. Most of your companies are not going to work out, so you need to make sure that you've got a good portfolio of companies that will make up for the losses.

I think a lot of people don't realize that when they get into venture, they need to first ask themselves if that’s really the right path for them long term.

Any VCs that you look up to or that inspire you?

I think my co founder, Scott, is a good example. He had a very successful career as an operator, and he wrote a very cool book called The Fuzzy and the Techie. I think we're a good pair because I bring a lot of that “scrappy founder” to the table.

He brings a lot of his operational expertise, and he's super smart, so he can really talk about everything from space to alternative beverages and have a good opinion on all of them.

One recent angel investment you’re proud of?

We tend to back mission-driven founders, so ones that want to make a positive impact on the world, and Jessica is a great example. She founded a company called Guaranteed after going through a very hard experience with her family.

A family member got very sick very quickly, and had to be put in hospice, and she realized what a horrible experience his end of life was, especially around hospice. So she decided to quit her job at Instagram where she was a growth expert and come up with a great solution for end of life.

It's a little bit of a taboo subject. People don't want to really think about it, but it shouldn't be this kind of horrible antiquated experience.

So I'm really proud of Jessica and Guaranteed, and she's doing great things. She's raised some money recently and is building a great team, and she bought a hospice group which is so thrilling.

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