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Startup Pitches, HR Tech, and Career Progression: Taylor Weiss from PeakSpan Capital

Recorded live at the HR Tech Conference from the Fuel50 booth in Las Vegas, Chad & Cheese sit down with Taylor Weiss, a Technology Investor at PeakSpan Capital. Taylor discusses her role, preferences for startups, emphasizing the importance of honest, succinct pitches. The conversation explores tech founders' ages, backing the right founder, excitement for innovative solutions in HR Tech, and leveraging AI for career advancement. Taylor stresses honesty's significance in career progression, proposing early education on self-awareness. She advises startups to align with investors' ethos and highlights PeakSpan's focus on alignment with entrepreneurs. To learn more about Fuel50, visit


Chad: Coming to you live from the Fuel50 booth at the heart of HR Tech, it's the Chad and Cheese podcast. We are diving deep into the world of HR technology, tackling workforce challenges with innovative solutions, and we'd like to give special thanks to Fuel50, the scienced-based talent marketplace that bridges skills gaps, unlocks hidden potential and supports better retention and engagement. Let's do this.

Intro: Hide your kids. Lock the doors. You're listening to HR's most dangerous podcast. Chad Sowash and Joel Cheesman are here to punch the recruiting industry right where it hurts, complete with breaking news, brash opinion, and loads of snark. Buckle up boys and girls. It's time for the Chad and Cheese podcast.


Joel: Oh yeah. What's up everybody? It is your poker dealer's favorite podcast, AKA, the Chad and Cheese podcast. I'm your co-host, Joel. Joined as always, the Paris to my Treasure Island, Chad.

Chad: Yes sir, so classic.

Joel: We are recording live from the Fuel50 booth at HR Tech in Las Vegas. And we are excited to welcome Taylor Weiss, technology investor at PeakSpan Capital to the podcast. Hello Taylor. What's up?

Taylor Weiss: Hello. Hello. How are you guys? Thank you so much for having me.

Joel: Relax. It's okay. It's okay. Relax. [laughter] So our listeners probably don't know who you are.

Taylor Weiss: Thank you.

Joel: Give us the Twitter bio. Give us the elevator pitch. You get pitched all the time. Give us your pitch.

Taylor Weiss: I do get pitched all the time, yeah.

Joel: Tell us about Taylor though. Long walks on the beach. You like hiking? I mean, what does the inner

Taylor look like?

Taylor Weiss: How did you know?

Joel: See, okay.

Taylor Weiss: Wow. No. I'm a senior associate, at PeakSpan Capital in San Francisco, doing this for a little over half a decade, in investing growth stage software companies. I absolutely love it. And I do love long walks on the beach with my dog and...

Joel: And what's your dog's name?

Taylor Weiss: Asri, yeah.

Joel: Asri?

Taylor Weiss: Asri.

Joel: Oh, okay.

Taylor Weiss: Yeah.

Joel: How'd you come up with Asri?

Chad: Asri? Yes. Let's get...

Joel: How'd you come up with the Asri. Yeah.

Taylor Weiss: I was in Bali. I actually used to live there.

Joel: You were in Bali?

Taylor Weiss: I lived in Bali.

Joel: Holy shit. That's awesome.

Taylor Weiss: For a segment of my life.

Joel: Wow.

Taylor Weiss: A very short summer. And there's a word in Balinese called Asri a A-S-R-I. And it means a

calming presence within nature.

Joel: Nice.

Taylor Weiss: And a sort of happiness. And I put a U in there so that Americans would be able to pronounce it correctly. [laughter] And that's what I named my dog.

Joel: So what is the antithesis of that? Because that's what Joel is.

Taylor Weiss: Okay. [laughter] I don't know.

Chad: Be careful. We're just starting the interview. [laughter] Be nice.

Taylor Weiss: Is he mean to you like this all the time?

Chad: This is how this works. [laughter] It's all good. It's all good.

Taylor Weiss: I thought you were the Paris to his Treasure Island. What's going on here?

Joel: I know. I'm supposed...

Chad: He'd like to see my treasure island. You know what I'm saying? [laughter]

Taylor Weiss: When in Vegas, maybe.

Joel: Moving on...

Chad: Where are we? I wanna point out something for the kids.

Joel: Yes.

Chad: You said half a decade, which is a great way to make you sound more...

Joel: Yes.

Chad: More experienced.

Joel: 6 years, yes.

Chad: Than your... Not five year... Half.

Joel: I love it.

Chad: Half a decade. So for the kids out there, that's much better than five years.

Joel: I love that.

Chad: I love that. I do love that. Good for you. Good for you.

Taylor Weiss: He's six and a half, seven years, so.

Chad: Which I'm sure as the technology investor, being younger, talking to the young founders is a positive. So talk about your role as the technology investor at PeakSpan.

Taylor Weiss: Yeah. Now, it's wonderful to talk to younger founders. We have a... Amazing company, that was started by some younger founders called Arist, who does learning, micro-learning in the flow of work. And being a younger founder, being a younger investor, I absolutely love it because you can really just understand exactly where they're coming from, you know what they're thinking and kind of where they came from and why they started these businesses. But it's not always a positive because when you're...

Chad: Okay. [laughter]

Taylor Weiss: A young investor, you're talking to folks who are a lot older, a lot more experienced. So it's...

Joel: Do you have older versions of yourself where you kind of play your good cop act or?

Taylor Weiss: Of course.

Chad: And is this on the founders' side?

Taylor Weiss: Absolutely, Chad.

Joel: Yeah. Okay.

Taylor Weiss: I definitely do.

Joel: See. [chuckle]

Chad: And this is on the founders side.

Taylor Weiss: On the founders side for...

Chad: That are pitching you for capital.

Taylor Weiss: Yeah. We have older founders, younger founders.

Chad: Yeah. So what's the average age of a tech founder these days?

Taylor Weiss: That is such a great question and I haven't really thought about it. I've never gone into a meeting and thought, "Wow, this person is over the average age."

Chad: Just role the dice, give me a...

Taylor Weiss: Of a founder, probably...

Chad: Give me a ballpark eyeball number.

Taylor Weiss: Probably...

Joel: 30.

Taylor Weiss: I would say. Yeah. Mid thirties, forties. I would say I have seen a lot of younger founders within the more recent years. And I love it. I think folks are more empowered to start their businesses.

Joel: Yes.

Taylor Weiss: At a younger age, people are dropping out of college and starting their businesses right after everything happened with Stanford, Harvard, Bill Gates, all of that, so.

Joel: So tell us what excites you most about talking to founders on a daily basis? Because there are...

Taylor Weiss: Oh, so many things.

Joel: Huge issues, huge problems that have been around for decades, centuries in some cases. What excites you about finding the solutions?

Taylor Weiss: It's such a great question because there's so many things to be excited about. I think what I love about this job is getting up every single day knowing that I get to go meet, talk to, and work with some of the most brilliant minds or the most brilliant future minds of technology that's going to be advancing the world as we see it today.

Joel: So what part of that excites you the most?

Taylor Weiss: Oh. The eccentricity of all the founders. The constant drive.

Joel: Talk to me about solutions though. All that stuff. They should all have that.

Chad: But this is interesting. She's really focused on the jockey...

Joel: Well, which is...

Chad: And not the horse.

Joel: Which I agree with 100% because I believe, personally, and tell me what you think, that founders make the company.

Chad: Yeah. Is it the jockey or the horse? Where do you... Where do you stand on that?

Taylor Weiss: I think in the beginning it's definitely the jockey, it's the founder, because that's really what you're backing in the beginning. You don't have much data...

Chad: Yeah.

Taylor Weiss: To go off of. Once you've got some data, you've gotten some customers, you've gone through a few renewal cycles, then you're backing both of them. When you're in the earlier stages like I am, you have to make sure that you're backing the right founder. So that's where we're focusing on today. Of course, being in that emerging growth category, you're kind of getting to the stage of go to market mechanization where you will be backing the horse and the jockey. But no, it's a great question. I'll go back to answering it. What am I excited about? Solutions. So we're at HR Tech, I am excited about finding companies that are able to give folks a career that they love and doing that in ways that hasn't been done before. And I think that you can do that in so many different ways, right? You can leverage AI to really just push the envelope on understanding what skills are needed for a job. You can push on, pay transparency and make sure that your entire culture is being valued and being paid correctly and equitably. You can push on engaging your employees and retaining them and making sure that you're creating a place where people wanna be. So there's multiple different segments of what people are doing to create a forever home and a forever career for folks like you. For folks like me, for folks like you. That's what excites me.

Joel: So we talked earlier about like DNA, right? You want to try to sequence the DNA, right? Which I think a lot of companies have tried over the years and they failed dramatically. How do you think we get to the point where we can effectively find that DNA, that skills, DNA, that culture DNA of that person, and then start to plug it in, because I think that's a hell of a lot harder than actually mapping the genome itself, right?

Taylor Weiss: Yeah, yeah, exactly. So the topic that he's talking about is in medicine, you can map the genome and you know exactly what is there. And from knowing that you know it's good for, you know it's bad for you in your work and in your career, a lot of the time in a job description, it might not be the skills that are needed. Or in a career, it might not be what's best for you. So if we're able to drill down into, honestly, what are my skills? What aren't my skills, what could they be? And then from the other side, look at what does this job need? What are those skills? How can I develop that within talent? And how can I foster a culture and community that breeds transparency and happiness and engagement and continues in that flow forever? And so being able to execute on that through technology is the question. How does that get solved? I don't know. But I think AI is going to be leveraged in there somewhere.

Joel: Yeah.

Taylor Weiss: 100%. And the way to do it is really understanding through honesty and transparency and equality.

Joel: I think honesty is the hard part, right?

Taylor Weiss: Honesty is the hard part.

Joel: Because what candidates are honest on their resume and through the interview and what companies are honest in what they actually need, and if they're transparent, what their real culture is. So is that really almost like the missing ingredient is honesty from both sides of the tracks? And if it is, how the hell do we get people to tell the truth?

Taylor Weiss: I have an answer for you.

Joel: Okay.

Taylor Weiss: And I think it has come from...

Chad: Just make sure it's truthful. [laughter]

Taylor Weiss: It is. This is the most open and honest and vulnerable I've been, no, but I think the honest answer for you is, before you get into your career, you're not honest because you don't know yourself, right?

Joel: Yeah.

Taylor Weiss: When you start to get into your career, you figure out what you like, what you don't like. It's like dating, you date a few people, you figure out what you like, what you don't like. You find someone to marry you, you settle down, you figure out your life.

Joel: Don't say Tinder for jobs. Don't say Tinder for jobs. [laughter]

Taylor Weiss: No, no, no. That's not what I'm saying. Please don't associate my name with that. [laughter] But I think as you get into your career, you figure out what you like to do and what you're good at, and you're able to become more honest with yourself maybe two years, three years, four years, five years into your career. What if we could push that into the education system when you're interviewing for jobs? So we could go to universities and we could push that, "Hey, you know what? Here's what you're good at. Here's what you're not good at." And have that life experience come a little bit earlier. And that honesty might therefore come a little bit earlier on both the applicant and the employer side. So I think just pushing that honesty earlier in that lifecycle might be a way it could happen.

Chad: We have a lot of companies that listen to our show and a lot of startups who are looking to raise money, looking to get in front of people like you. What advice would you give them? One, in terms of how do

I get in front of you? And how should the conversation go when I do get the facetime?

Taylor Weiss: How do you get in front of me, man? Go for it. Just go for it. I really like to talk to everybody that I can.

Chad: Yeah.

Taylor Weiss: That's why I'm sitting here with you guys because I just love talking, as you can tell. I think the best way to get in front of an investor is to be focused on what you're doing, know your product, be able to have your elevator pitch down in like 30 seconds, two minutes or three minutes. Figure out which one you need to do. And when you do get in front of an investor, I think the most important thing is really just like I said before, just knowing exactly what you're trying to execute on and...

Chad: Yeah.

Taylor Weiss: Know what you're not good at and what you're asking for.

Chad: So tips for a good deck that I show you. Give us some quick pointers.

Taylor Weiss: Short.

Chad: There it is. How short?

Taylor Weiss: Easy to understand. [laughter]

Chad: Give us some context. 1 slide, 5, 10?

Taylor Weiss: Look, I absolutely love a thick deck that I can get into and it's really juicy and it gives me a lot of information and detail, but I also love a short one where I can understand it really quickly. So if I have maybe a three to five page deck...

Joel: Okay.

Taylor Weiss: That's wonderful. I think that's great.

Joel: And keep the juicy deck for later.

Taylor Weiss: And then we can dive in. But I think a three to five page deck that is very focused. You're laughing at me.

Chad: No.

Joel: It's okay. It's just because we're both...

Chad: Save me Chad. Save this. Save this.

Joel: We're both 12-year-old kids.

Chad: Yes, we're children.

Joel: So here's the thing that I think is interesting because you are not right. Right? Your funds are not right for certain founders and...

Taylor Weiss: Sure.

Joel: And certain organizations, how do they know which organizations, which investors to actually approach because there are so many that are out there. How do they know? I mean, are you guys pretty forthright? Like look, here's... You have to meet these five bullets. If you meet these five, we're there, is pretty much all investment firms like that or no?

Taylor Weiss: No.

Joel: No. Okay.

Taylor Weiss: I don't think that...

Joel: Okay.

Taylor Weiss: All investment firms are like that.

Joel: Okay.

Taylor Weiss: I think a lot of investment firms are looking for the same type of thing, which is high growth, high retention, potentially profitability in the later stages.

Joel: Yeah.

Taylor Weiss: I think what's most important to PeakSpan is alignment with the entrepreneur.

Joel: Okay.

Taylor Weiss: And knowing what firm to look for and who to talk to, I think comes with conversations with folks at the firm. And you'll talk to PeakSpan and in one conversation know who PeakSpan is and you will know if... That this is the firm that's right for you or not.

Joel: Should that be the standard for every founder that's out there, so they're not wasting their time with some investors?

Taylor Weiss: Yeah.

Joel: If they don't know from the first call, then it's probably not the one for them.

Taylor Weiss: I think I can stand by that because at PeakSpan within the first call you will know, within the first 20, 30 minutes of talking to us if we're the right firm for you.

Joel: Got you.

Chad: Taylor, thanks for hanging out with us in the Fuel50 booth here.

Joel: Yeah.

Chad: For our listeners that want to get in touch with you, maybe shoot you a juicy deck, where would you send them?

Taylor Weiss: You can go to my LinkedIn or you can send it to my email

Joel: Nice.

Chad: This was fun, Chad.

Taylor Weiss: Thank you so much for having me guys.

Joel: Of course.

Chad: Thanks for joining us. That's another one in the can from the Fuel50 booth at HR Tech in Las Vegas. We out.

Joel: We out.

Outro: Thank you for listening to, what's it called? The Podcast, the Chad the Cheese. Brilliant. They talk about recruiting, they talk about technology, but most of all they talk about nothing. Just a lot of shoutouts of people you don't even know. And yet you're listening. It's incredible. And not one word about cheese. Not one cheddar, blue, nacho, pepper jack, swiss, so many cheeses and not one word. So weird. Any who, be sure to subscribe today on iTunes, Spotify, Google Play, or wherever you listen to your podcasts. That way you won't miss an episode. And while you're at it, visit Just don't expect to find any recipes for Grilled cheese. It's so weird. We out.


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