The Angel with Michael Conniff

Michael Conniff (00:00)
Hello again, everyone, and welcome back to the accelerator with Michael Conniff. I am super pleased today to welcome to the program. Did I say the accelerator? I meant the angel. I got my podcast confused. This is the angel. You're an angel, Chado John. He's our guest. He's the director of growth at GitHub, but that's not the only reason why he's here. He's really here because he's a very active angel with a company called

Chiedo (00:13)
Hahaha.

Michael Conniff (00:28)
Rockworks and he's got over a dozen, I'm sure it's over a dozen by now, right? A dozen angel investments. So Chado has managed to do that. So welcome to the podcast, Chado. Great to have you.

Chiedo (00:35)
Yeah.

Yeah, thanks for having me, Michael. It's called Rock Town, just to clarify, but you were close.

Michael Conniff (00:47)
Okay, I appreciate that. And I wanna remind everyone out there, this is the angel, not the accelerator, despite my mistake. Both of these podcasts can be found on a Substack, go to theaccelerator .substack .com. We're also on all the major audio platforms, Audible, Amazon, Apple, at least a dozen, I think, plus on Spotify and YouTube for...

what I guess we could call full motion video, though we don't really move very much. But Cheydoz, you're a really interesting story, I think, because you have a full -time job, and yet you appear to be almost like a full -time angel. So let's take those in kind of reverse order. Let's start with the angel, because that's the angel in you. What...

Chiedo (01:28)
Correct.

Yeah.

Michael Conniff (01:43)
made you want to be an angel and when did you start?

Chiedo (01:47)
Yeah, great question. So I've loved startups for as long as I can remember. My dad, my father was born in England. I was born in England. My dad was born in Sierra Leone. When I was about six, he moved to the US to get involved with the dot com boom, see what was up with technology, taught himself how to code and made a successful life for himself in the US. So I grew up with a father who was extremely entrepreneurial. So from the youngest age, I mean, back when I was in like elementary school,

I was building computers, writing HTML. And in middle school, when I told my dad, I said, Hey, I want to go work at seven 11. I'll make some money. He said, if you want to make money, start a business. And so from middle school onward, I was just always starting businesses, trying to figure out how to make some money here and there as a young man. And I went to James Madison university in Virginia, got my computer science degree. I did some freelance work on the side there, SEO, web development, consulting here and there.

Um, had a few part -time jobs as well. And then when I graduated, I couldn't quite pull the trigger to go work for someone else. I obviously eventually did, but at least initially I started a web development consultancy firm, uh, with the goal being to, uh, support innovation, work with startups, um, and do a lot of cash, uh, plus equity deals, you know, venture studios, what they call it today. And, um, that was a lot of fun. It was terrible business. So eventually, you know, it got burnt out.

And we shifted.

Michael Conniff (03:16)
Why was it a terrible business if you don't mind my interrupting?

Chiedo (03:21)
Yeah, for sure. I mean, just the economic model, right? So I was running a brand new company. I was paying software developers who were initially kind of new to it. I was hiring folks out of college and folks at the start of their career. But the longer they worked for me, the more expensive they became as they became more skilled and moved further in life when they needed money for a mortgage, money for a marriage, money for a child.

Health insurance. So my costs are increasing rapidly while I'm doing work with amazing startups. But the reality is nine out of 10 of them fail. And what's the most important thing for most businesses? Retention. So like out the gate, we're doing work with clients where nine out of 10 of them are going to fail. Just kind of like, you know, by default, regardless of how great of a job we do. And with most of them, we're not getting paid what we would get paid.

Otherwise, so we're doing huge discounts, 80 % discounts, pushed off for equity. And so the profit on one side and the expenses, just the hardest time making those things match. So initially, folks were coming to work in sandals and I was wearing my sleeveless shirts and always telling folks, we're never going to grow up. We're never going to do any of this business stuff. We're young, we're fun.

Eventually, man, I was wearing the suit and the tie flying around the world, making the sales. Yes, sir. Yes, ma 'am. I was polished. And so we landed some good business. We pivoted, we shifted. I got burnt out though. I wasn't really doing what I loved at that point as well. Also became a dad along this journey. And so around year eight, I'd hired some amazing people to run the company. Head of sales, head of business, head of office manager.

and got an amazing job offer at GitHub, which is the best thing for me, my family at that time.

Michael Conniff (05:25)
Yeah, so you mentioned your dad was a coder. And of course, GitHub is nothing but code, right? I'm not intimately familiar with the company, but tell us what GitHub does and maybe how that relates to sort of your investing and what you're looking at.

Chiedo (05:34)
Hahaha.

Yeah, for sure. So I mean, the easiest way for kind of most people to think about GitHub is we are where developers collaborate and write code together. So an analogy, a lot of people write docs together on Google Docs. A lot of developers write code together on GitHub. And there's way more. So we're also driving the AI revolution as far as code is concerned. AI copilots, GitHub copilot. So we're enabling developers to write code faster.

by having AI at their side. I'm not replacing the job, but assisting it. How does it relate to what I do? I try and keep those worlds really separate from an investment perspective. So I've got what I do at GitHub. And there's a world where I could invest in the developer tool space, which is the space GitHub's in. But I try and steer clear from that out of fear of potential conflicts of interest.

Michael Conniff (06:38)
Sure. I did notice though on your Rockwork site that you have made several AI investments. So one interesting question I think a lot of people are, this is kind of front of mind. What do you look for in an AI startup? Because there are now, like overnight, there are, I want to say millions, but let's just call it tens of thousands of AI startups.

So how do you differentiate? What are you looking for?

Chiedo (07:09)
Good question. So the first thing is I'm not looking for AI startups. The same way I'm not looking for internet startups, I'm just looking for startups and AI happens to be how most of these startups are going to win. The same way now, you know, most of these tech startups, they're incorporating a mobile app. They're incorporating the internet because it's the latest technology and it's extremely helpful. So what do I look for in startups? So a few things. I actually have a list. So one kind of like a problem I'm interested in.

to like, oh man, there we go. This Apple thing always. Boom, there we go. Boom. A big, hairy, audacious goal. I know these computers. So big, hairy, audacious goal is from this book. Good to great, built to last, there it is. A burning problem that's solved today but poorly, right? So I want it to be a burning problem that people are solving.

Michael Conniff (07:47)
Computers never work.

Yeah.

Chiedo (08:07)
just with like a really lame solution. But they're doing it anyways and paying for it because the solution, the problem is such an issue, that's an opportunity. High problem frequency, so something that folks encounter regularly. So as far as what I'd invest in, would I invest in an Airbnb? Maybe not today, just based on how I'm thinking about signals, right? Like obviously if I knew it was gonna win, I'd invest, but you don't.

I'd rather invest in an Uber, something that folks are going to use daily, not every few months. There are a few other things that I could cover like target customers, willingness to pay, team that's worked together, ideally second time founders, but I won't go through the whole list.

Michael Conniff (08:49)
What, what now, now what's your average check size or pardon me, I should say in the, in the, in the lexicon of angels, I should say, what's your ticket size? I love that word. What's your ticket size? It's like, you're like going to a movie. So, so how small is small? A thousand, a couple thousand.

Chiedo (08:55)
Super small, right?

Hahaha!

Yeah, yeah, that's fair. So the smallest check I wrote last year was 1 .5K and the largest one was 15K. So what I try and do though is I try and get on deals with other angels, right? So if you get like three or four of them together and we're each writing, you know, 5K to 15K checks, it can be something a little bit more substantial than a small individual bet.

Michael Conniff (09:35)
Okay, so you've really thought about this, which I like. You have a, you know, you've codified, to use the coding word, right? You've codified what you're interested in, it occurs to me. Maybe the apple did not fall far from the tree. But essentially, when you get in, I asked you like how small is small? How early is early? What's the earliest you've gotten in? What's your...

Chiedo (09:45)
Hahaha.

Heh.

Michael Conniff (10:03)
What's your sweet spot in terms of getting in?

Chiedo (10:06)
Yeah, what's the earliest I've gone? Okay. Let me think. I think most folks that I've invested in are post product, but almost all of them are pre revenue. So usually some sort of kind of MVP. So I'm generally not investing at the idea stage, but that's not something I wouldn't do. It's just harder, like, you know, at the earlier stages, there's so little signal to get as far as what.

Michael Conniff (10:22)
Okay.

Chiedo (10:36)
Um, what a founder can do, how they can execute, um, seeing them execute some sort of MVP helps you get some sort of signal. Uh, if I knew, um, if I knew a founder, uh, you know, I definitely invest in the idea stage or if somebody came highly recommended, um, I just haven't come across that yet.

Michael Conniff (10:56)
You know, it's interesting about that. I just, I've been in communication with a founder, honestly, who is driving me nuts because, you know, I've introduced him. I help out this media fund at Holt family exchange called Holt intersection fund. And, you know, he, I got him a presentation to our committee and,

Chiedo (11:05)
Ha ha ha.

Michael Conniff (11:22)
It was pretty clear and I knew I sort of knew this going in, but like he was so persistent. He didn't have a product. He doesn't have a product. And so and so he's too early. He's too early for our fund, right? He's got a good idea. He's actually vis -a -vis what you look for. You know, he's established at a very interesting pain point. But but he doesn't have a product. And so here's here's why I'm bringing this up.

Chiedo (11:32)
Yeah.

Michael Conniff (11:52)
So I have basically told him that 10 different ways, like trying to be nice, like, look, you need an MVP. You need to be able to show. And this happens all the time, right? Great idea. It may even be a long kind of fairly far along, but no product, you know, no product. And so what this one entrepreneur said, and I think this is also very telling, he said, well, that's why I'm asking you for the money.

That's why I need the money so I can have make the product. And I think that if, this is sort of a funny thing to say, but I'm really looking for, I guess, entrepreneurs who can make the product without the money. At least initially, right? How do you feel about that?

Chiedo (12:37)
Yeah, yeah, for sure.

Yeah. Yeah. So, you know, one of the things that, you know, on my list, I didn't get to is, and I got this straight from this guy named Jason Calacanis, but what, you know, what he looks from what I look for now is, um,

Michael Conniff (12:50)
I know Jason, yeah, Jason actually just forgive me for interrupting, but 20, 30 years ago, I was asked to do an article called, What is a block? And I interviewed him at length. He was one of the only people blocking at the time and the rest is history. He's had a long and illustrious career as an angel, but go ahead. So what's the other thing?

Chiedo (13:03)
Yeah.

Yeah.

Yeah, for sure. Looking for builder founders. So ideally, you have one founder who can write the code, one founder who can design the thing, and maybe one of those founders or even a third founder who has experience leading growth at a company. So like selling the thing. That's the ideal because when you don't have those, you have lots of folks who, it's fine, it's just different skill sets. But...

It's just generally not what I want to invest in. I have a couple of times, I've been learning a lot, but you want to have folks who can get their hands on the keys, get scrappy and build a rough version of the thing and test ideas. Because when you don't have that, you've got all these misaligned incentives, especially when folks work with venture studios, which is not a knock to venture studios, like I used to run one, but the incentives are misaligned. So sometimes to get the product to market, it's going to require like a thousand hours.

Right. And so when you're paying somebody else to do that, now you've got this weird tension versus when you're doing it yourself, right. You're just going to put in the time. So last quick point. So what I tell folks is they're kind of like two ways to start a business in my opinion. Right. So one is either with time and energy. Right. So you need to be a builder, founder, or with money and experience, meaning you've got the money to pay someone to do it. But it's really hard to be a founder who

can't put in the time and energy to get something to market and also doesn't have the money and experience to get something to market because then you more or less just need to sell somebody on a vision. And like if you're really charismatic, you can, but it's a much harder journey.

Michael Conniff (14:53)
Yeah. So one other quick, quick, uh, true story. Another founder I was working with had an AI product actually before chat GPT came out. So it was early and, um, it, it, it, it, it was very, it was very interesting. Um, but he, he said, you know, I can't get anyone to invest in this because I need $30 ,000 to do the user interface. And so, um, I was like,

That's, you know, not that much money. Like figure out a way to get somebody to do it, you know, figure out a way, find a way. I mean, isn't that isn't that what entrepreneurship is? It's like, you know, you know, if you can't do it without the money, you're going to have, you know, if money is going to dictate everything. So here's the true story part of it. Here's why it's interesting. No kidding. Within two months, two months from that, he still had not gotten his user interface finished.

Chiedo (15:30)
Ha ha ha.

Michael Conniff (15:52)
He still, you know, he was stuck on this 30 K number and guess what? He reached out to Mark Cuban and Mark Cuban came back five or six times by email. He sometimes answers his own email, you know, and but this guy didn't he didn't have he didn't have the product he had. He had stalled out, right, because he didn't get that 30 K. And now he's got like a very serious shark. I say that in the best sense.

ready to, you know, kind of looking for reasons to back him. And he, Cuban didn't back him. And I think it was because of what had happened three months before. Like if he had solved that riddle, then I think there was, it was a much better chance. So anyway, it's an interesting conundrum. I wanted to ask you, so is the size of check and ticket, like what would, would you be in a,

different situation and is it your ambition to be in a situation where you're writing bigger checks, that you're making bigger bets? Is that something you would like to do as you grow into this?

Chiedo (17:01)
Yeah, for sure. I would just need to get much wealthier. So I'm still like what? I'm like 33, so I'm at the start of my career. But one of the things I am doing to write bigger checks is I'm actually launching a venture fund. So the venture fund that I'm launching is going to be focused on planet impact. And we're going to write 50K to 100K checks. And I'll be able to do that because the venture fund model, just for the listeners, angels invest their own money. So I'm severely limited on that front with the amount of money I can invest. And venture capitalists invest other people's money.

Michael Conniff (17:05)
Hahaha!

Yeah. Yeah.

Chiedo (17:31)
And so we've been raising this fund, asking other people to give us their money for us to invest it on their behalf. And that opens up the opportunity to make bigger bets and get in deals that wouldn't allow you to get in with a 5K or 15K check.

Michael Conniff (17:48)
And how does that change your investing? How will that change your investing? Obviously, you've done this intentionally. You want to play a bigger game. But how is it going to change things for you in terms of your decision making?

Chiedo (18:03)
Yeah. So there's two things. So one on the angel front, kind of investing individually. You know, part of my strategy is I'm investing a lot, right? Investing a lot to diversify, but then also invest in founders, right? Just to build the relationships. And even if this startup doesn't work, maybe the next one does, right? So just being there, being in their corner at the early days is sometimes beneficial, but also I'm learning. I'm learning a lot about various industries.

various business models and really sharpening myself as a business leader generally, which is also beneficial to my role at GitHub as a director of growth and anything I do here in the future. And all the work I do on the venture fund. Then on the venture fund side, we have a very specific thesis. So most venture funds or a large amount of them, they need to have some sort of kind of like story focus so that when you ask folks to give you money, they say, what are we investing in? And you tell them. So...

On the venture fund side, we're very specifically focused on this planet impact space. Even more specifically, the circular economy, which is kind of getting things reused and getting things reused as opposed to, you know, used and thrown away. And so on that front, we're building out a whole program where we invest maybe even earlier than I angel invest, but we're able to do that because I have a couple of partners. One.

who runs an accelerator program that she's been running for the past seven years or so. And then another who's going to run portfolio support.

Michael Conniff (19:35)
And who is, and who are they and where are they?

Chiedo (19:39)
Yeah.

Yeah, Amu Fowler and Callie Keene. So they're both up in Northern Virginia. And I met Amu just, you know, Virginia has a startup ecosystem. We were both a part of it. And then I met Callie through Amu.

Michael Conniff (19:56)
And where are you based, Cheto?

Chiedo (19:59)
Harrisonburg, Virginia, Shenandoah Valley.

Michael Conniff (20:02)
near James Madison, right? Isn't that where James Madison is?

Chiedo (20:05)
Yes, what brought me. That's what brought me here and I fell in love with it. Couldn't leave and here I am.

Michael Conniff (20:08)
More or less. Yeah, yeah.

I actually, I think I told you this when we first zoomed, I told you that I once did a basketball game at James Madison University on the radio for the University of Vermont. So I've been there. I've been in a beautiful spot, beautiful spot. So yeah, no, that's interesting. Is that a kind of a hotbed of entrepreneurship?

Chiedo (20:24)
Hahaha!

Yeah, I love it.

Michael Conniff (20:37)
been venture capital and one wouldn't necessarily think of it. And also the question is how far from Washington DC area?

Chiedo (20:45)
Yeah, how far from Washington DC? Maybe two hours, two hour drive. So not too far. Like I fly out at Dallas Airport when I travel. We are investing globally though.

Michael Conniff (20:51)
Okay.

Is it, is it, it's, yeah, yeah. But is there like a little bit of an ecosystem there for you?

Chiedo (21:02)
Yeah, a growing one. So you have James Madison University. You have the Stanton I -Hub. You have a few things. Yeah, so a large part of what we're doing is we're also trying to build it. But we acknowledge that it's going to take some time. So we're going to invest in US, UK, Canada, but then also be right here.

Michael Conniff (21:25)
What are the startups that you've invested in as an angel that you're most excited about?

Chiedo (21:31)
Oh man, you're gonna get me in trouble. Alright, so I won't tell you.

Michael Conniff (21:36)
You know, it's...

Well, go ahead. Forgive me for interrupting. Go ahead.

Chiedo (21:42)
No, it's okay. I'll give you, you know, I'm interested, I'm excited about a lot of them, but I'll name a couple. So one, there's this company called Strata. There's this, this is very techie, but there's this automation suite called MuleSoft, which allows you to connect various systems, you know, at a large enterprise to get them to talk together. MuleSoft is, it goes back to what I talked about, about like folks solving a problem.

with something that sucks. Like no offense to MuleSoft. But it's very hard for developers to use and developers are often asked to set it up. And so they're trying to create a developer first alternative to what MuleSoft is doing. And I love that. I felt the problem. I remember we tried to offer those services way back when and ended up deciding like, no, this is too much. You need like a specialized consultant. So they're trying to disrupt that. And then the other thing is Ribbon.

Ribbon, one of my good friends, Alan Olo, he runs Ribbon with Said. And Alan went to Eastern Mennonite University right down the street here and Said went to UVA. And they're building a platform to make inheritance transfers more effortless, which one thing I love about that is,

Like we're clearly at this point in history, like the why now is very strong where over the next 10 years, a lot of money is going to be changing hands. And currently, you know, it's a very, you know, the problem is not solved. You know, how is that money going to change hands? Lots of phone calls and lots of letters in the mail. And they want to get ahead of that front run it and digitize it.

Michael Conniff (23:25)
But you know, actually, I wanted to make I have my my trusty notebook here, but I did speak to somebody who is basically works with a whole raft of family offices last week. And he said, actually, I don't even have to look at my notes. He said that we're in the midst of and he really focuses on family offices. Right. So he said we're in the midst of the largest transfer of wealth in history.

And basically it's the transfer from, you know, people my age to people your age. It's the baby boom to the next, you know, to the generation behind it and or two generations behind. And he said, I believe that he put the number at $72 trillion of wealth moving from one to another. So that's an opportunity. But what does the company actually do?

Chiedo (23:55)
Yeah.

They're building a platform for credit unions, banks, and they've pivoted a few times. So initially they were working on kind of like a B2C option where, you know, say you had a, you had a loved one pass and you had a death certificate, you would upload it to Ribbon and they would get in contact with everyone on your behalf. Recently, they've shifted to a B2B model where they're providing that platform to banks and financial institutions, starting with credit unions.

And then those credit unions will have that kind of service they can offer their customers.

Michael Conniff (24:55)
So it's inheritance and also would it be estates?

Chiedo (24:59)
Yeah, yeah. And this is where you start to get past my area of expertise, inheritance versus states. It all kind of like bundles up in my mind, but that's just because I haven't dug too deep into... A loved one's passing away yet.

Michael Conniff (25:14)
Yeah, yeah. So it also would seem that there's, I mean, a while ago, somebody came to me and said they wanted to teach the younger generation of family office in family offices what to do, because, you know, that generation, you're part of that generation. You can speak to this far better than I. But but, you know, basically, it's a different generation than what's come before in the sense that, you know, they care about things that.

They're kind of very motivated. They're probably far more political than what came before in some respects, though not all respects. So that seems like a great opportunity. Okay, you gave me two. Can you give me one more?

Chiedo (25:58)
Yeah, I can give you one more. So the third is probably, oh man, I'm going to get in trouble here, but probably Hiroshi. So Hiroshi, they're building a platform and service that makes it easy for folks in Africa to do business with folks in America. And so primarily shipping and transactions. So if you want to order goods, products, inventory from American vendors,

in Africa, which happens more often than you think, it's very difficult to order something from Amazon, right? Because you need a US address. You just need these things that we take for granted here that you can't always bank on in certain parts, Nigeria or Sierra Leone. You can't bank on specific address postal system and all of that that we take for granted here. So they're creating...

a logistics business that takes care of all of that and they're doing amazingly well so far.

Michael Conniff (27:02)
Oh, that's great. When you say amazingly well, what do you mean? Do they have some traction?

Chiedo (27:06)
Oh yeah, yeah, yeah. They've got, they've got a lot of traction. I mean, I can't speak specific numbers right now, but they, um, yeah, I mean, you can, you can Google them. They're, they're very much in business with lots of reviews and the finances look amazing. Hero, she, so like hero. Yeah, like hero, like you're my hero. And then she.

Michael Conniff (27:18)
Say the name again? Is it hero, harrow? Or roeski?

Hiroshi, okay, that's great. So I think, you know, I've been following you on LinkedIn closely. You post a lot. You're very interesting. What you post is always interesting. So kudos on that. But my question to you, and I actually think you're kind of a role model for somebody to...

Chiedo (27:29)
Ha ha ha.

Michael Conniff (27:52)
dip their toes in the water of being an angel. Now you've done far more than that, but you had to get started somewhere, right? So you still are holding a full -time job at GitHub. You're investing. Now you're talking about a fund. So what would your advice be to people listening to this podcast, which is called, let's face it, The Angel, how to go about becoming an angel? What would your advice be? What would be one or two things you'd suggest?

Chiedo (28:13)
Yeah.

Yeah, for sure. So there are a few things. One, join a syndicate. So Jason Canacanis has one. I think it's just like thesyndicate .com, and there are a few others. One of the nice things about a syndicate is syndicates, they send you lots of deals, so lots of startups and lots of due diligence that you can review and learn and get a sense for what to look for. And I always tell folks, look at like,

Michael Conniff (28:34)
Yeah.

Chiedo (28:48)
five to 10 of them before you make an investment. Because when you start, everything looks amazing. So first, you're like, oh, yeah, this is great. This is the future. And then after you've talked to like 100 startups, you start to see the patterns. And you're like, oh, OK, so like everyone's doing X, everyone's doing Y. I might not want to invest in this. And like, everyone's charming. And then the third thing, I don't know, just like read some books, listen to some podcasts. There are a bunch of good ones out there. So much information is free now on the internet.

Michael Conniff (28:57)
That's true.

Yeah. Yeah.

Chiedo (29:18)
Yeah, the Angel by Jason Kettelkannis, that's amazing as well. And I know I recommend him a lot because I've learned a lot from his content. And then even there's this book called The Business of Venture Capital, which you don't need to read as an angel investor, but it helps you understand like more of the landscape and what's going to happen with your companies like down the road. Those are good things. Then joining an angel group as well helps a lot.

Michael Conniff (29:26)
Yeah.

Sure.

Yeah, and don't forget to listen to a podcast called the angel. So I want to remind everybody out there. This is the angel. We're the companion podcast to the accelerator. Michael, if you're a host, we're on all the major audio audio platforms, including audible, Amazon and Apple. We're on video and audio with Spotify and YouTube. And the best thing to do is to subscribe.

Chiedo (29:47)
There we go.

Michael Conniff (30:10)
to the Substack newsletter that also carries the podcast. It can be found at theaccelerator .substack .com. I wanna thank you, Chato John. You are really super impressed with what you've done, with the resources available, and I'm sure you're gonna do great things in the future. So thank you so much for being our guest today.

Chiedo (30:37)
Thanks, Michael.

Michael Conniff (30:40)
And thank you all out there for listening. And remember, as I like to say, we'll have we'll be back with another podcast before you know it.