Lessons From An Investor Who Has Backed 200+ Startups

Jason Kirby 00:00.168

normal intro or whatever but go to the point you were just talking about.

Adam Spector 00:03.66

Yeah. So, so Jason, was just, you know, mentioning how, one of the key like pet peeves of mine as maybe like, look, as a four time founder, investor in 200 plus companies is the, the, if there's anything that I've learned, and also this happens to you start getting a little bit older in life is you start realizing like your time is so, so, so precious in, in how you allocate that time in where you decide to spend it in who you decide to spend it with is maybe the most important decision you will make in your entire life. So literally.

I've decided to spend this hour with you right now, Jason. I'm never going to get this time back. So I hope it is worthwhile, but I'm never going to get this time back. Right. And so that has to be good investment of my time and hopefully a high ROI for either me personally or for my business or anything else. And if it's not, I should just say no and not do it. And what, what pisses me off is I come across a huge number of founders in my day to day work. Right. So I I'm the CEO and founder of Chore.

We do back ops operations for startups. We essentially take on all the annoying, almost like admin that you need to do to run your business. You have to do HR. You have to do compliance. You have to do finance. You have to do equity. You have to do that stuff, but it is not your core competency as a business. It is not why you exist. It is not why you started your company. If it is why you started your company, then you should be competing with me, which is cool. Like we should do that then. But like, if it's not, then why the heck are you spending any time in this?

What I was ranting about, you when we started to kick this off was I actually talked to a founder today, but it happens all the time. He's like, look, I'm a first time founder. I just feel like I need to understand and learn this stuff. And I was like, that is why you're going to fail. I mean, I kind of just called him out. I'm kind of just like, like, if you think that is a good use of your time in that you think you need to learn, like I use the example of, you know, love him or hate him. Like Elon Musk is an amazing entrepreneur. And I was like, do you think Elon Musk?

Jason Kirby 02:50.056

Well, I think that's a great introduction to, uh, no, I loved it. And that's why I want to go straight in and I want to hit on this a little bit because there's, definitely, there are some things to know how they work as a founder, but do you have to be an expert at them? Do you have to spend hours doing the work to figure it out? No. And that, I think that's, I'd be curious, like with the founder, if this was a pattern or if it was like one particular thing, like payroll, yeah.

Adam Spector 02:51.982

Sorry, sorry for the rant.

Jason Kirby 03:19.016

Like it's a commodity. There's no.

Adam Spector 03:20.92

So I would actually even disagree with you a little bit on the statement you made there, Jason, which is like, I don't actually think you need to figure out a large majority of these things as a founder. I think as a founder, your only job is to set the course of your company. And that means you need to set expectations and goals. And so you say, my goal for my HR team, if we're gonna stay on that topic for a sec, my goal in the HR team is when people are, we hire people really well, we do great hiring, we find great people.

We get them onboarded quickly. We make sure they get paid on time. And we don't spend too much money doing it, right? We don't have like the gold plated platinum plan. Those are the things that I would set up for my team. And then my job is to make sure I hire the experts, either internally or as outsourced experts to go get that done. I don't care about the details. I don't need to know the details. It does not matter to me. And the same thing applies to your marketing team, your sales team, your product team, your engineering team, right? You know, same thing, like, actually, this founder, I even asked him, was like, well, who's running your engineering? He's like, well, it's my co-founder. Like, so do you need to know the details? What are you doing? He's like, no, I trust him. I'm like, well, why don't you hire someone that you do trust for all your back office operations? And just let it get done. Like, just, you don't need to know it's happening. And that's what good founders do. They set the guidelines, the principles and the rules for how their business needs to be run. And then they get out of the way.

Jason Kirby 04:56.05

So you have a unique insight because you've backed over 200 plus founders as an angel investor. And I'm curious to kind of see like what drew you to that conclusion. I imagine you're seeing certain behaviors across all your investments over a decade and looking at various different founders work out and create a unicorn versus those that don't. What would you say are some of the attributes that you've recognized across all those investments that kind of adhere to that thesis?

Adam Spector 05:25.538

Yeah, absolutely. And in, I'll say I've learned, I've also had this honed in a little bit more because I also run something called the Entrepreneurial Excellence Podcast. So I speak with a lot of these founders in the one answer. One word answer to your question is obsession. So the most successful founders are the ones who are utterly obsessed with the problem they are solving to the detriment of everything else. So, so going back to this founder, this example, he—he's building an AI company—and yet...

He's worrying about what payroll provider to use or what equity platform to use and how to set it up properly and all these things. That guy isn't obsessed. I'm sorry. He's not, it's not worth my time. He's going to fail. Now, he might come back as a second time founder. He was like, "Look, I'm a first time founder, just feel I need to learn this stuff." Cool. Second time founders come back. This is why second time founders are more successful. They realize like there's a lot of things that they can just set aside and not care about.

Jason Kirby 06:50.342

When it comes to seeing that obsession and looking at, you see the consistency in terms of first time founder versus second time founder with that particular trait or is it a kind of crapshooter? It's not necessarily as clear.

Adam Spector 07:04.566

It's easy to say it's first time versus second time founder. It's actually not quite that clear though. It actually really comes down to… (sound cut) the intelligence of the founder, and I think their ability to think from first principles. And so if they say to themselves, "What do I care about? What is my superpower? And how do I enhance that every day?" That is where they will be successful. And sometimes I come up—we have many customers and many investments of mine who are first time founders, and they're incredibly successful. Although I will say many of the unicorn investments that I've made, the large majority of those are second time or multi-time founders.

But we've met many customers who are very successful first time founders and they just realize like, "This isn't work I should be doing."

Jason Kirby 07:57.2

No, it's valid. And yeah, I wouldn't be surprised. I wouldn't say it's odd that your second time founders have better outcomes because they did have those learnings early on and they had to kind of grind and suck it up and eat dirt for, for quite some time to figure it out and not have the outcome maybe that they were hoping for, or maybe have a decent outcome and then come out better, bigger next time.

Adam Spector 08:13.678

But I will say what shocks me still a little bit is the proliferation of knowledge, right? Podcasts like your own. There's so much knowledge out there, right? This guy literally had a phone call with me— not saying like I'm someone so special—but like, "I'm gonna have a phone call." Sit there and ask me questions. If nothing else, then, "Alright, cool. We're not a fit for you. We don't want to pay for your product." Awesome. Ask me a ton of questions or here's my advice. You're getting it for free. Here's my advice: don't use us, but just don't waste your time on these things.

And yet he just doesn't care. And this is where it shocked me. Like there's so many things I don't know about. I will try to go get, learn about them. I'll use AI to go learn a little bit. And then I will try to go hire an expert and I can go tell that expert, "Here are the goals that I expect. Here's the outcome that I'm looking for. Can you hit it?" If the expert says yes, we will pay them for that outcome. And if they don't hit it, we fire them. And it's very straightforward—it’s a clear business transaction. I don't need to hire someone to do it. It's a win-win.

Jason Kirby 09:13.928

Do you think there's anything from the standpoint of like abundance mindset versus scarcity mindset with those types of founders?

Adam Spector 09:25.39

Great question. I'm a huge believer in— to me, I don't think people, it's maybe a little bit different perspective in the world. But yes, that is, as an early stage founder, you tend to be very cautious with your cash, understandably, right? You have very little cash, you're very frugal. It's like the ramen founder—you're just eating ramen every day, making no money, trying to like scrounge whatever money you can for everything. Cool.

You should be super cheap and you probably should only be doing like, "You have your laptop, you have an internet connection, you have enough money to pay for like AI credits or something, right?" Like, cool, that's it—go crush, get that done. The moment you raise money though, you need to switch from a scarcity mindset on cash to an abundance mindset on cash and then move from a scarcity mindset on time to an abundance mindset on time. Right? So when you're a founder, two founders,

Adam Spector 11:49.962

No VC is ever going to say, "Congratulations, you are so freaking cheap that you saved an extra 40 or a hundred K or whatever, but you didn't hit any of your milestones." They don't care. On the other hand, a VC will say, "My God, you crushed your growth metrics and you hit those numbers. You blew past our expectations in 12 months." You will get unlimited amounts of cash and you can keep your business going. So many founders fail to make that switch mentally from once again, scarcity of cash to time scarcity.

Adam Spector 12:01.542

The moment you get funding, you are time scarce, which means you need to delegate and outsource everything that is not critical to your business.

Jason Kirby 12:21.934

I think that's a valuable lesson for a lot of founders to realize because I see a lot fail to make that transition of like not ramping up the hiring, bringing on the talent and growing as fast as possible because that's the cost—the cost is the game you play when you take venture money. And a lot of founders don't take that into consideration.

Adam Spector 12:21.934

The reason they don't is, I get it. It's easy to feel like you're doing your job well by being really frugal. It's sort of this easy thing to control—like how much money you're spending. It's much easier to control your cash outflows than to control whether you get new customers or if your product may hit the next milestone. So it feels like you're doing your job well. But once again, no VC cares. They do not care that you optimize your cash spend so you can live super cheaply.

Adam Spector 13:15.784

I literally don't care. Go spend—go live at the Four Seasons in Hawaii and get it done, but go crush. Dope.

Jason Kirby 13:30.446

So let's talk about your background—as you know, you're an entrepreneur, obviously made tons of investments as an angel, but you've also built and sold companies. So let's give the audience a little bit of background on your entrepreneurial journey, building and scaling companies.

Adam Spector 14:29.28

Yeah, I mean, the short version is I actually started from my first business back in high school. I sold stuff to my friends in high school and grew from there to have a sort of standard path. After that, I was the good first son—I went to Vanderbilt undergrad, went to grad school for JDMDA, thought I was gonna be a lawyer like my dad—but realized really quickly I had no interest in being a lawyer. I got a job in strategy at a cool midsize tech company in DC. I remember thinking, "I was like the guy who's reading Wired before it was cool to do so." I still get the paper version of Wired. I've probably been one of their longest ever subscribers. But I was like, you know, DC is not the center of the tech space...

Jason Kirby 15:24.58

…still do it.

Adam Spector 15:26.804

If you want to be at the top of your chosen profession, you need to put yourself in a place where you can be a part of that. I learned that lesson when I sat down with a founder backed by Sequoia in DC—pretty rare at the time. He said, "If you want to be in politics, stay in DC. If you want finance, go to New York. If you want media, go to LA. If you want tech, go to the Bay Area." I went and got a job at a tech startup out here. The company eventually got acquired for $400 million. I made a bunch of money in my stock equity grant—I was like, 'Welcome to Silicon Valley.' This is what you expect.

Jason Kirby 15:36.934

Did you raise venture for any of your past companies?

Adam Spector 15:38.828

Yeah, so the first three were all venture backed. I think at this point we raised 30–40 million total in venture dollars—not quite at your level, but a decent amount. And then my current company, Chore, we actually decided to be bootstrapped. It’s a different perspective on things.

Jason Kirby 16:07.868

Yeah, so let's dive into that—launching Chore and choosing to bootstrap. What was the methodology behind that?

Adam Spector 16:15.374

It was necessity. Invention is the mother of all necessities. Essentially, just before the pandemic in 2020, I was a co-founder of a company called Abstract Ops. Our thesis was to handle operations so founders could focus on what they do best—building their companies.

Jason Kirby 16:22.247

You…

Adam Spector 16:44.738

You don't need to reinvent the wheel. Why reinvent how to run operations, bookkeeping, or legal work when experts already do it? We raised about $10 million from top-tier VCs, but in 2022 when we went for our Series A, things changed.

A lot of our revenue was from services, which many startups try to pass off as tech. VCs weren’t buying it. So we made the tough decision to split off the services part, and eventually we pivoted to build Chore.

Jason Kirby 17:34.49

…it.

Adam Spector 17:42.382

We split off. It wasn’t a legal spin-out, but they assigned all their customers and revenue to us. We grew from a team of seven to over 40 today.

Jason Kirby 19:13.329

Hmm.

Adam Spector 19:32.334

We kept doing the service side of things. To finish answering your previous question: you can’t raise money for a services company in 2022. Now, the world has changed a lot in the past two years and VC interest comes in regularly. And when I say “we’re not interested in taking cash,” it gets them even more energized.

Jason Kirby 19:53.256

Yeah, no thanks.

Adam Spector 20:01.55

We split off—it wasn’t a legal spin-out, but they essentially assigned all their customers and revenue to us. We’ve grown significantly.

Jason Kirby 20:17.704

Nice. And what kind of operations do you take over for founders?

Adam Spector 26:18.286

With Chore, at a high level, you’re almost hiring a fractional chief of staff. Most companies don’t need a full-time chief of staff—and a good one is very expensive. Instead, we take on all the nitty gritty tasks. Everything from HR (onboarding/offboarding) to running payroll, handling compliance, managing vendor communications, and even setting up a full diligence folder for fundraising is managed by us.

Jason Kirby 27:05.234

Yes.

Adam Spector 27:15.502

I’m sure you know this yourself, Jason—when you have to go find a file, you’re like, "What did it say? Is it in Gmail? Google Drive?" Meanwhile, I’m doing a fundraise and have to spend thousands on legal fees to build a diligence folder. We handle all that, including managing your mail so you never have to worry about it.

Jason Kirby 27:46.888

As I look at the mirror.

Adam Spector 27:49.834

Exactly. So as a founder, I don’t want to open any mail. My team handles it so I can focus on what matters.

Jason Kirby 28:19.75

Every month I get to go into the Excel sheet and it's like, "Are these 13 things that we can't figure out?"

Adam Spector 28:26.382

Right. And what if you had someone to do that for you and be the point person to get it done?

Jason Kirby 29:28.626

You know, it's great that you bring this up because I feel like I could see why founders maybe get hung up on doing it themselves rather than delegating.

Adam Spector 29:58.19

And it sure, it only really takes an hour if you're doing one task—but most founders procrastinate it because it's not their core focus. They spend four times as much time worrying about it as actually getting it done.

Jason Kirby 30:24.238

And then it's like, "But it's still on your mind."

Adam Spector 30:53.761

Exactly. It’s the opportunity cost of your time and all the context switching. Instead of dealing with payroll issues on a Friday night when support is closed, you simply forward the email to your team.

Jason Kirby 30:59.63

And what size of companies do you see as the best use case for Chore?

Adam Spector 32:10.568

We’re ideal for companies with anywhere from 5 to about 75 FTEs. Typically, businesses that are generating at least $500K per year or have raised funding—this is when VCs start saying, "Hey, you need to move fast." We have over 60 testimonials, and customers say we save them 5–10 hours a week. That’s around 500 hours a year—an extra three months of time for a founder.

Jason Kirby 32:17.82

Yeah.

Adam Spector 32:24.686

But if you have a million dollars in a checking account paying zero interest, you’re effectively paying your bank—say, $40K a year. Move it to a bank that pays 4% APY and that’s $40K in free money.

Jason Kirby 33:05.644

That was just like, you're off the cliff. If you don't do it, you're off the cliff.

Adam Spector 33:08.268

You probably are. It is what it is.

Jason Kirby 34:15.822

So I've run across that myself. I have a real estate portfolio and run Thunder full time. I used to get texts in the middle of the night about these issues. Now, I have an assistant who handles it.

Adam Spector 34:23.782

Congratulations.

Jason Kirby 34:36.732

And yeah, the time management is key.

Adam Spector 34:47.416

Correct. It’s about spending your time where it matters most.

Jason Kirby 36:00.332

And you’re not just running Chore; you’re also an investor. How do you split your time between analyzing deal flow and running Chore?

Adam Spector 36:21.986

It’s funny—earlier today I had a call, and it sparked an idea. I’ve always been one to “double dip” on things. In college, I did two majors and a minor by taking courses that counted for multiple credits. I apply that same principle now. For investing with Chore, I talk to hundreds of startups every day. It’s not a pitch—it’s a conversation. I learn about what they’re doing, what they’re raising, and whether I should invest. That way, I can do both without missing a beat.

Jason Kirby 37:47.513

Zero chance, I assume?

Adam Spector 37:48.718

Yeah, zero chance. I hope he learns from it, though. I’m always looking for founders who blow my teammates away.

Jason Kirby 38:51.176

And how do you balance family and work? It seems like you structure your life so that even if you're investing or running Chore, you're always where you need to be.

Adam Spector 39:11.734

Exactly.

Jason Kirby 39:20.616

That's the beauty of today's society. You get to chart your own path.

Jason Kirby 39:25.518

I saw you’re also involved with the Autopilot Fund. What’s that experience like?

Adam Spector 39:45.56

Correct. The Autopilot Fund is actually my third fund. My partner and I set it up to have dry powder to invest in the best companies. We focus mostly on underlying data sets for AI, though we invest in other areas too.

Jason Kirby 41:07.474

So do you raise outside money from LPs as well?

Adam Spector 41:16.102

Yes, we do. That brings its own level of responsibility. I started investing in 2011—just after I moved to San Francisco. I realized early on that there are so many opportunities out there that many people don’t have access to. I attended countless events, met founders, and even one memorable investment was in a company called Human Interest. I sat down with their founder, Roger Lee, over coffee and was blown away by his obsession.

Jason Kirby 43:00.316

What are some of the other companies you’re proud of investing in?

Adam Spector 43:11.086

One interesting one is Diamond Foundry, the first synthetic diamond company. Another was a company offering executive coaching for everyone, which seemed revolutionary at the time. And then there’s Even Up, a legal company, and Checker for background checks. They all made sense to me.

Jason Kirby 44:15.43

Yeah.

Adam Spector 44:33.666

They just made sense at the time, even if they sounded crazy to some.

Jason Kirby 44:43.186

It’s a lot of fun being in the thick of it out in San Francisco, soaking in that energy.

Jason Kirby 45:03.982

How is San Francisco right now? Is the news covering it appropriately?

Adam Spector 45:03.982

No—the news is meant to shock and entertain, not to report facts. Parts of San Francisco are challenged, but many neighborhoods are crushing it. The food is amazing, and it’s become the center of AI. I love walking in my neighborhood and seeing people having walking meetings—all from major AI companies.

Jason Kirby 45:43.08

Hard to disagree with that statement.

Adam Spector 45:59.34

And it's all here. Plus, I've been here 15 years. The weather, the food, the proximity to the beach and mountains—it’s all fantastic.

Jason Kirby 46:31.464

It's great to finally hear some positive words about San Francisco.

Adam Spector 46:42.786

Exactly. Though areas like the Tenderloin and Union Square have their challenges, most of the city thrives.

Jason Kirby 46:50.61

Yeah, that's where I was at with him.

Jason Kirby 46:57.192

It's been a long time, yeah.

Adam Spector 47:12.616

And it gives San Francisco a bad name sometimes because people who aren't used to it get a negative impression.

Jason Kirby 47:20.704

Yeah, LA and San Diego are not far off.

Jason Kirby 47:30.906

That's Adam—it's been an absolute pleasure having you on the show, talking about how founders should prioritize their time. And for those interested in Chore, what's the best way to learn more?

Adam Spector 47:46.03

Go to highertour.com to reach out and learn more about what we're building. You can also follow me on LinkedIn—just search for Adam Spector.

Jason Kirby 49:10.065

Great, great lead in.

Jason Kirby 49:16.296

And thanks so much for being on the show. I look forward to getting this out to our audience.

Adam Spector 49:25.474

My pleasure, Jason. Thanks for having me.