Investor Stories 373: Key Advice (Holloway, Felesky, Droesch)

Investor Stories 373: Key Advice (Holloway, Felesky, Droesch)


On this special segment of The Full Ratchet, the following Investors are featured:

  • Katelin Holloway
  • Adam Felesky
  • Mike Droesch

We asked guests for the most important piece of advice that they’d share with folks early in their venture career.

The host of The Full Ratchet is Nick Moran of New Stack Ventures, a venture capital firm committed to investing in founders outside of the Bay Area.

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Transcribed with AI:

0:19
Welcome back to TFR on today’s special segment, we ask guests for the most important piece of advice that they’d share with folks early in their venture career. Here’s the segment called key advice.

0:36
On today’s special segment, we have Caitlin Holloway of 776, Caitlin, if you could share one piece of advice with a young, new investor, what piece of advice would you give them? Strive

0:46
to actually be helpful. I think that you know, the number one thing I hear from founders is investors make a lot of promises. That’s what we do, right? We’re compelling humans. We are sales people. We’re trying to get, you know, the very best deals in our portfolio for those outsized returns. And the reality is, is that portfolios grow the shiny new thing comes along next, and a lot of folks don’t honor their commitments. And so if I were a young investor, which I am, which I was recently, I think the number one thing that helped me really build my personal brand as an investor and therefore collectively build the brand at 776 is I try to do my best to honor my commitments and find unique ways in which I can be helpful. And sometimes it’s small. It’s, you know, it’s remembering birthdays. It’s tracking pregnancies and making sure that they’re being supported as as people, right? That’s the easy stuff. Be a human, be, you know, actually ask them how they’re doing when maybe things don’t go well after you get off a board meeting, call that that maybe didn’t go so great, or, you know, you were they their numbers weren’t what they expected. Have a follow up call. Say, how you feeling? How’d that board meeting make you feel? So I think that you know that that feels so table stakes to me, that feels so simple is to just like be a human, show up as a compassionate, empathetic person, but you know the reality is, is there’s going to be so much more that goes wrong than goes right in this in this life. And that sounds like a downer thing to say, but like being a founder is one of the hardest jobs on Earth, it’s also one of the loneliest jobs on Earth, and showing up with introductions and network and capital and great advice is good and important. Ironically, to have. You know, a good portion of investors don’t show up with any of those things, although they committed to them. But as a young investor, one of the best things you can and I learned this from Alexis, actually is founders are going to remember the people who impacted them in those early days when things really, really were hard, and based on the odds, some of those founders are going to go on to actually fulfill the potential that they promised you or that you saw in them when you cut that first check. And they’re going to look back several years later, and they’re going to remember you, and that is how you build that network, to make sure you know where the very best founders are moving. You know about the cabin here. And so not only is it very helpful to you and your brand and building your book and building your network and relationships. It’s also the right thing to do as a person, and I love it when you have that, you have your cake and eat it too. Yeah,

3:49
no, that’s a great point.

3:58
On today’s special segment, we have Adam filesky of Portage, Adam, if you could share one piece of advice with a young new investor, what would you tell them a young

4:06
new investor, that’s right, and they’re investing in privates or just in general investing

4:13
a venture investor, but young, whatever you want,

4:17
Look for a young VC investor, I would say, meet as many entrepreneurs and and individuals that are working within companies. Build your network. Get informed. And quite frankly, you probably shouldn’t be in VC yet. Go get operating experience.

4:38
Very good. You Mike, on today’s special segment, we have Mike drosh of Bessemer Venture Partners, Mike, if you could share one piece of advice with a young, new investor, what would you tell them?

4:53
Yeah, I’d say, you know, the people that are successful in this job, I believe they do it. You know, one they’re. Are obsessive about it, and I think this because they just genuinely love it. And so I one of the pieces of advice I give to people is like, first, like, make sure you really love it, because if you don’t love it, it’s going to be hard to have the level of obsession you need to keep going and, you know, and to be able to grind it out over a really long period of time. And so often that looks like, find, find the categories, the stage, the you know, the types of companies that you truly love spending time with, because that’s much more likely to make you successful and and somewhat to go along with that. Also, like, find your style. There’s just so many ways to be good at this. There’s no, there’s no one path to success. And I think you know there’s, you can see people who are really successful at blogging or Twitter events, or they’re going to do dinners every week, or they’re going to do really deep, thoughtful content or something. And I think it’s really hard to be good at all of them, but I would try to pick the one, you know, you know, pick podcasts, you know, find, find what you’re, what you’re great at, you know, and go really deep on that.

6:00
I’ve had so many young people come to me and say, Yeah, Nick, I’m not going to start a podcast so, you know. And I say, you don’t have to do that. Pick something that’s a fit for you, for what you enjoy, and just, you know, focus.

6:19
That will conclude this installment of investor stories. If you’re enjoying the program and would like to see it continue, take a moment and leave a five star review in iTunes. Okay, that will wrap things up for today until next time over. Prepare, choose carefully and invest confidently. Thanks for joining me.