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https://www.thisisgoingtobebig.com/
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Summary and Timestamps
Charlie O'Donnell, a seasoned venture capitalist and author shares his thoughts on fundraising, coaching founders, mastering conversations, and navigating the startup journey. This episode offers a deep dive into the mental models, communication strategies, and long-term thinking that fuel successful entrepreneurship.
In this episode:
The importance of storytelling and community engagement in book publishing
How founders can use "conversational judo" to steer difficult talks
The role of coaching, reflection, and transparency in startup success
Strategies for managing co-founder relationships and ownership issues
The mindset of navigating failures and raising capital with optimism
How to think in infinite vs finite games within entrepreneurship
Practical advice for early-stage founders on discipline, planning, and dealing with uncertainty
The influence of "finite and infinite games" in entrepreneurial resilience
Balancing realism and optimism in investment and team-building
The impact of parenthood on leadership and life balance
Resources, book recommendations, and upcoming conversations with founders
Timestamps:
00:00 - Welcome and overview of the episode’s themes
04:00 - Common pitfalls of startup storytelling
07:00 - Using conversational judo to navigate tough questions
09:00 - Coaching founders: reflection, boundaries, and strategy
12:00 - Negotiation, selling, and understanding your audience
15:00 - Controlling the arc of a conversation: framing and temperature checks
18:00 - The importance of honesty, transparency, and feedback
20:00 - Building co-founder trust and handling ownership questions
23:00 - Managing startup risks and planning for uncertainties
27:00 - The balance of optimism and realism in venture investing
30:00 - The real value of co-founders - someone to be honest and push back
33:00 - The power of structured financial plans and strategic discussions
36:00 - Long-term thinking and planning: lessons from successful entrepreneurs
39:00 - Disciplined experimentation and hypothesis-driven meetings
43:00 - The art of managing founder and investor relationships
45:00 - Navigating binary choices and abundance mindset in venture
50:00 - Reflecting on failure, resilience, and infinite game thinking
55:00 - How family and personal experiences shape risk and optimism
60:00 - Practical resources, book suggestions, and upcoming projects
64:00 - The influence of AI, parenting, and future of work on entrepreneurship
About Charlie
For 20 years, Charlie has been a mainstay in the New York City startup and innovation community–starting as the first analyst at Union Square Ventures after working in the General Motors pension fund’s venture capital and private equity group. He went on to help First Round Capital open up their NYC office in 2009, where he sourced investments in GroupMe, Singleplatform, Moat, and Backupify among others.
In 2012, he started Brooklyn Bridge Ventures–the first venture capital fund based in Brooklyn– and funded over 100 local startup companies including Hungryroot, Petal Card, Brigit, Shortcut, Radformation, and Imagen, while also building a reputation for being the most accessible early-stage investor in New York.
Brooklyn Bridge Ventures made its final investment in early 2023, resulting in a portfolio where 40% of the companies were female-founded, 30% have a BIPOC founder and 9% have a Black founder, reflecting the diversity of the city’s entrepreneurial workforce and the firm’s dedication to inclusivity.
Charlie is one of only a dozen individuals named to Business Insider’s 100 Most Influential People in NY Tech five times or more and has been featured on City & State’s Tech Power 50.
He has spoken at SXSW and Techcrunch Disrupt and has taught entrepreneurship and various other business and technology courses at Fordham University and NYU-Poly. He is also on the leadership committee of Tech:NYC, an industry group representing New York City’s technology industry with government, civic institutions, in business, and in the media.
In 2010, after volunteering with the Downtown Boathouse in Lower Manhattan for seven years, he co-founded the Brooklyn Bridge Park Boathouse to promote human-powered boating in Brooklyn Bridge Park and safe public recreational access to the East River and New York Harbor. The program, which he has recently returned to as President, put 9,000 paddlers on the water in 2022 thanks to the help of over 150 volunteers.
Charlie competes in triathlons and is a member of the Brooklyn Triathlon Club. He also competes with car traffic as a New York City bicycle commuter. He is an 18-year veteran of the same local co-ed softball team, which he captains, and can regularly be found on Prospect Park’s ice rink playing goalie on Friday nights in the winter.
Charlie is a resident of Park Slope and the President of the Co-op that he lives in with his wife and daughter. You can find his writing at www.thisisgoingtobebig.com since 2004.
Transcript
Daniel Stillman (00:00)
Well, Charlie, I really do appreciate you making this time. I know you said you're the ultimate extrovert, you're like, let's go hard. Let's keep going. They also say that you really should not write a book unless you are happy to talk about that book a lot for a long time.
Charlie O'Donnell (00:16)
And market it. Yeah, that's, I actually think that when people ask about, you know, the decision to write a book, I mean, I guess people could sort of self publish, but I really think that ultimately the way the publishing works now is people get books who publishers think can sell them and who are willing to go out and talk to a lot of people about them. And that is, you know,
Daniel Stillman (00:17)
Yeah.
Correct.
Charlie O'Donnell (00:43)
how good of a writer you are is probably secondary to that. So ⁓ sort of the nature of the industry now. I hope I'm a little bit.
Daniel Stillman (00:47)
Yes.
Right,
right, which, you know, of course, like as a fellow author, I have self-published and published. And when people ask me like, ⁓ I think there's this tiny moment of micro ⁓ validity when people are like, did you self-publish? Or honestly, I think publishers do very, very little for you. If you're going to do do again, my advice would be self-publish because, you know, you clearly have a platform and you clearly can't.
talk to a lot of people about the stuff, but that's not what we're here to talk about. That's just my, that's my.
Charlie O'Donnell (01:26)
I think it's interesting. So first of all, I was approached by my publisher and it's actually a very indicative story of how I interact with the community. My publisher, this guy Phil Marino from Wiley, he's an absolutely terrific guy, lives in Brooklyn. And he had a startup idea years ago and
thought about pursuing it, found one of my community events, followed me, poked around the ecosystem, thanks to my newsletter and whatnot, and realized this is in fact really hard and maybe this idea is not the right idea. And so we went back to publishing or decided not to leave, but glommed onto my writing through that exploration of entrepreneurship. And... ⁓
Daniel Stillman (01:57)
Mm-hmm.
Mm-hmm.
Yes.
Charlie O'Donnell (02:23)
It's not surprising to me that that's how I wound up doing a book is that somebody in New York who was exploring entrepreneurship found me because I try and make myself findable to entrepreneurs.
Daniel Stillman (02:33)
Yeah. Yeah.
Yeah. Yeah. No, that's a fair point. And you're a great writer, by the way. I've enjoyed your writing a great deal. Well, so we're already well before the cart and the horse, but I want to we're in it. I still want to officially welcome you to the conversation factory. And I'm grateful for the time. And congratulations on the book. Great job. It's a great book. I love the story of how you how the book kind of found you or you found the publisher.
Charlie O'Donnell (02:39)
Thank you, I appreciate that.
We're in it.
Thank you.
Daniel Stillman (03:00)
through community and you do a lot of work around community and clearly the community is supporting you as you roll the book out. I mean, I was at an event of yours on Tuesday. I didn't even know you were when I signed up for it. I thought the topic was interesting and then I was like, Charlie's talking at it. Like, of course. So it seems like you're everywhere, which is great. Good job.
Charlie O'Donnell (03:18)
And Cat
was super cool for putting the QR code up, the whole panel. And ⁓ that was really, really terrific of them. And I really enjoyed that conversation.
Daniel Stillman (03:25)
Yeah.
Yeah, is it great? And there's some things I want to peel the onion back on. first of all, like, what's the one message from the book that you feel like people might miss? Because like a book, it's a it's a big book. Some people don't even get past the free sample. And some people might read the book, but but miss the core message.
Charlie O'Donnell (03:49)
So my biggest worry is that the book is discouraging and I don't want it to be discouraging. And, you know, I wrote a post today about two sort of mildly comparable startups and one that I had backed in the micro mobility space, scooters and whatnot. And there's another company that recently got profiled in ink.
Daniel Stillman (03:55)
Hmm.
Hmm.
Charlie O'Donnell (04:19)
that's building, I don't know if you call it a scooter, company called Infinite Machine. It's kind of scooter-like. And this recent company got...
Daniel Stillman (04:28)
These are the ones that are
like that the sexy Tesla Cybertruck baby. I read the essay, but I've seen the scooters too. They're amazing looking scooters.
Charlie O'Donnell (04:31)
Yeah.
Yeah, they look like
they're right out of, know, the RoboCop should be riding them, right? And it looks like they're very futuristic. ⁓ And that company got $14 million of funding and the company that I backed a few years ago did not. And that company struggled to raise. ⁓ And also one of the sort of variables in there was ⁓ Hispanic immigrant founder. And it's just very easy to put those two
Daniel Stillman (04:41)
Yes.
Charlie O'Donnell (05:05)
companies up there and to say, well, we all know what's going on here. Right. And there are lots of things you hear in the venture ecosystem about who gets funded and who doesn't. And in this post today, I tried to peel back the layers of like what I actually think is going on. And some of it, when I sort of got accused of throwing it back on the founder, it's just that the person across the table from you is trying to figure out whether you're going to build.
a Deca corn and IPO for $10 billion. And the people who do well at doing that think that's gonna what that's what's gonna happen from the beginning. And they're not afraid to say it. And they're even a little bit pushy about it, right? And not everybody who has varied backgrounds is comfortable, like being that person in the meeting. And so I sort of wrote about this and one of the first comments I got back
It was from a female entrepreneur who was like, this was hard to read, but I'm glad I wrote it. And I realized I have some work to do. Great. That like, that is exactly what I'm going for. Right. Because it isn't an easy read and some of it does kind of throw back on you and say, Hey, did you actually put the fantasy cashflow hockey stick in your, your deck?
Daniel Stillman (06:18)
Yeah.
Charlie O'Donnell (06:33)
because you might think it's BS, but signaling the intention to build a venture sized company is a prerequisite for getting venture dollars. And if you go back and you're like, actually, I didn't say it because I wasn't comfortable saying it. ⁓ That's hard, but ⁓ hopefully, ultimately it's helpful.
Daniel Stillman (06:36)
Yeah.
Mm-hmm.
Yeah.
Yeah, well, look, I appreciated. I think you're trying to thread a difficult needle. I read the essay. I thought it was very interesting. And when I pair it with the conversation you had with our friend, Lauren Pearl, about bias in the room, I think you were really trying to chase in that essay where the bias exists and where in the system a VC can really have an impact because saying that you should change your approach and how you pitch and speak to risk more.
⁓ or go for a broke and swing for the fences is very different than saying, maybe VCs should be hiring more diverse people to be on their staff so that in five years, those people are better networked and understand the game better so that when they have an idea and they want to pitch it, they're not just coming to an event trying to suck up whatever insight they can from writing and plug into the community that way. They're already in the community. And I think upstream
versus downstream solutions. That's what I heard you saying. But I also understand that you're you're you're walking a delicate line because I'm sorry, I, Lauren and I talked about it. Just like, yeah, I didn't want him to be right. This is hard. You're I don't I don't think you're blaming the founder. But what you're saying is in the room, the only things you can do are the things in the room and saying this is this is really like my whole chest like it's tingly with this because like saying
Charlie O'Donnell (08:05)
I'm
No. I know.
Daniel Stillman (08:20)
You can't complain about it, about inequality in the room. That's too late. You're saying the VC's job is to start now with building a more diverse ecosystem now. So I want to I want to pivot. I'm going to I know I'm to have to work very hard. I don't know if you know what your conversational style is. You you're you swing for the fences and you go for broke. So I'm going to just have to break in occasionally and try to rein you. And I hope you're OK with that, Charlie.
Charlie O'Donnell (08:49)
Yeah,
no, no, no, feel free. That's what I do to other people on panels. I totally get it.
Daniel Stillman (08:50)
Okay, good, good.
So my my second book is about designing conversations, which I think we are all designers of shapers of architectures of conversations. And I've heard you use the term conversational judo to describe. talked that you talked about this in the panel on Tuesday. You talked about this in your conversation with Lauren. The judo approach is to is to you're getting questions you don't want to answer or the conversations going in a direction.
where you don't want it to go and finding a way to elegantly see for the people listening, they can't see where my fingers going, but to elegantly pivot, to swerve, to say yes, and, and also I think the inner resources to do that are non-trivial. Now you can plan, but I'm just wondering how you coach founders to make sure they find the inner and the outer resources.
to understand what kind of judo they need to apply to get the conversation where they need to go, where they need to go get it. Now I'm, I can't finish that as an English sentence, but I'm going to pause and let you let that filter through your, your brain stem.
Charlie O'Donnell (10:06)
So I got asked a version of this question by somebody in a class that I spoke to who it resonated that they come from a particular background where prognosticating this big ridiculous future was not something that came easily to them.
And they said, how do you, how do you coach founder around that? And I said, you can't tell them to feel differently. That doesn't work. what you can do is objectively say, you have a sales challenge. The person across the table from you wants to buy a ticket to a very large outcome.
Daniel Stillman (10:46)
Hmm, yeah.
Charlie O'Donnell (11:04)
What are the things that you need to tell them to convince them that that's what you're selling? So take how you feel out of this, right? It's not about how you feel. It's how good you are at selling that particular product. And that's something that we can objectively talk about and put your feelings aside related to it. And so that's really where the coaching comes in is saying things like, you know, if you
Daniel Stillman (11:12)
Hmm.
Charlie O'Donnell (11:33)
a venture capitalist, ⁓ they know that the downside, ⁓ you need to figure out the upside around it or that yes, it is true that they're gonna ask a bunch of downside related questions, but like a good politician, you don't have to answer them.
Daniel Stillman (11:50)
Right. And just reminding them that they have a choice. Like their hand is on the steering wheel, too. And I think you're pointing to something that you when I think about negotiation theory, I always like to talk about my I went on the maybe the best intellectual vacation of my life. I went to Harvard for their negotiation intensive for a week. And it's like, you know, losing against some of the top lawyers in the country while, you know, taking copious notes. And then like by the end, you realize like
You need to ask more questions and you need to think about what matters to them. Often, I think when we're selling to someone else, and especially because founders are so passionate about what they believe and the vision that they want to create, it can come from a like, believe I want like, this is how I got here. And I think very often people like to explain their ideas about how they got there. And that's less important, certainly to the person across the table.
because they want to know where are you going to take this? What's going to happen next? What are you going to do with this money? And I think that's the sort of like the me and what I want and what I need and what I've been thinking versus the get out of my chair, go to the other side of the table and go sit in their chair and say, well, what what do they want to hear? What kind of things are music to their ears? So that sounds like that's you're advocating for the get out of my head approach and get into their head approach.
Charlie O'Donnell (13:16)
Yeah. And you know what also happens sometimes too? That how I got there thing, sometimes it's your own insecurity that goes into that because you're trying to prove that you belong in the room. The venture capitalist has already said that you belong in the room because they invited you. They're not there for free interview practice.
Daniel Stillman (13:32)
They invited you. Yeah, for sure. Yeah.
Right. Well, so I think the other I drew this diagram, which I can't I can't really show you because it's a tiny squiggle. When you were talking about how a lot of people leave the room without really knowing how they did. And I like to I think about conversations as an arc. And if we can architect them, it means that we got to think about the arc, which is like the beginning, the middle and the end. And you talked about somebody who
gets into the room and says, like any good teacher, presenter, learning development instructor say, hey, this is the room that I thought I came in. I think we need to talk about this, this and this. Like, do you guys agree? Is that what you're all here to talk about? Cool. Like, let's talk about it and then check in as we get towards the end and say, so we needed to understand this, demonstrate this and establish that. Like, how are we doing? Let's temperature check. How do we do?
And then say, you know, do you have any questions? And how come we're not a yes? Like you really there's a there's a very strong beginning, middle and end that you want founders to really be holding in. And a lot of the founders I've coached feel like they get lost in the swim because you guys can ask them questions right off the bat and they can lose control of that arc. So how can a person keep their hand on the wheel and guide the conversation through that?
where they wanna get it to.
Charlie O'Donnell (15:02)
Let me tell you, I am the world's worst passenger. And from literally, and I think it comes from, my dad was an absolute terrible driver. And as soon as he taught me how to drive, that was the last time I ever got in the car with him driving. And I'm not happy with anybody else driving and I can't sit there. And I am the same in a pitch meeting.
Daniel Stillman (15:07)
Ciao.
Hmm.
Charlie O'Donnell (15:31)
And so as much as you try and keep your hands on the wheel, I'm grabbing it and trying to take over. So you really have to hold on for dear life in a meeting with me. And it is not easy. And don't think your deck is going to be the structure of the meeting because I'm going to pass it or you're not even going to have a chance to put the deck up. And we're just going to start talking about stuff. so, yeah, you need to control the room.
Daniel Stillman (15:41)
Yeah.
Hmm.
Damn.
Charlie O'Donnell (16:01)
but also provide enough flexibility so that you can answer if I'm like, listen, I really want to know if you do X, Y, and Z. If you say, we'll get to that, well, I'm all ⁓ I'm thinking about is this thing, right? Whatever you say after that, I'm half paying attention until I get the answer to my one question, right? So the idea that, you know, I'm going to give you a podcast answer that's going to explain the whole thing, you know,
Daniel Stillman (16:11)
Hmm
Right.
Charlie O'Donnell (16:31)
And I'm better at criticizing it than I am probably actually doing it. But I think what's really important is to help the investor understand how to understand. So for example, one of the examples I use in the book is a nutrition bar company. And there's a lot of bars out there. Some of them clearly become
very successful. Like there's a lot of big exits in the bar space. I'm not an expert consumer investor, CPG. And so when I was critiquing ⁓ somebody's pitch around this, what I said to them was like, you need to explain to me why people win in this space. And here's a suggestion. It feels like in the food space, there are waves. There was the Atkins thing, and then everything has protein, and then there's some other thing.
If you tell me, listen, there's a bunch of waves and this current wave is hormone health in this case. And every wave produces a bar winner. And here's my, you know, three or four examples of one of those things. Then I'm like halfway there. ⁓ I see. Yeah, I could kind of buy the hormone health as the current wave. And now I'm bought in that there's probably going to be a bar winner in this space. So.
Daniel Stillman (17:42)
Mm-hmm.
Charlie O'Donnell (17:57)
All you have to do is convince me, it might as well be us, right? Which is much better than trying to convince me from scratch, well, how are going to do this whole thing and get the marketing out there?
Daniel Stillman (18:10)
Have you ever read the Challenger sale? It's one of these.
Charlie O'Donnell (18:13)
I have read
of it. am a really bad, you can do this with my book. It's fine as long as you buy the book. I buy a lot of books on Kindle and then read like a third of them.
Daniel Stillman (18:19)
Ha ha ha!
Sure, sure, Which third? The last? Some people are like the last page readers, you know, but this isn't a novel. It's not like the big big reveals on the last. It's some books are meant to be to be. ⁓ I think paged through, but yours has stories that I think are short enough that somebody could absorb them. The Challenger sale is a great audiobook, and they talk about this teach tailor and take control.
the three T's that the salespeople who in any market can take control of the conversation, tailor the message to the person they're talking to. I like actually know the thesis of the person and the teaching them something is kind of what you're talking about. The is leading with a hook that gives them something that surprises them. Getting their attention. Let me tell you, like, here's what I think you should know. And that's really
Charlie O'Donnell (19:15)
Let me tell you about this space.
Daniel Stillman (19:21)
putting the Minto pyramid like putting your conclusion way up front because it sounds like if you've got a Charlie O'Donnell in the room, that's like a land war in Asia or going up against the Sicilian when death is on the line, like, you're not going to be able to take control because they are going to have their own agenda. And they want to get to page five. And if you say I'll get to that, if I heard you right, we're losing you if I say I'm going to get to that. Yeah.
Charlie O'Donnell (19:46)
Right.
My four-year-old took control of a room yesterday by telling me that sharks have no bones.
Daniel Stillman (19:56)
⁓ That's strong.
Charlie O'Donnell (19:57)
I'm like,
I've seen shark jaws. You can't be right about this. And in fact, it's all cartilage. there's some problems, my wife and I went down a rabbit hole of like, sometimes there's calcification that comes from the water, but like, ultimately it's not under the strict biological definition of bone. But let me tell you, she commanded the world.
Daniel Stillman (20:07)
It's all cartilage. Yeah.
Yeah, she's up to date. Yeah.
Charlie O'Donnell (20:25)
She commanded the room. We were paying attention.
Daniel Stillman (20:28)
Yeah, assertion,
which really goes back to our early point about being able to say whatever you want to say with with confidence, which is much easier if you are if you've got some runway because you're not going to go hungry if this pitch goes wrong. Yeah. So you're a coach, you you I feel like you're less of maybe you're sort of in this transition period from.
Charlie O'Donnell (20:44)
Right, right.
Daniel Stillman (20:56)
You still talk about VC, but I have a feeling like you, when I, when I look at your emails, yeah, you coach VC is right. Exactly. Which is different than the kind of coaching I do, which is coaching founders and executives. I'm curious from your perspective, understanding founders and the company life cycle. Where well, a, I want to understand what your coaching philosophy is. Like, how do you think about coaching and how do you define coaching? But I'm also curious for the, the kind of people who are reading your book.
Charlie O'Donnell (21:00)
Which one sees now?
Daniel Stillman (21:26)
which is for founders is where in their life cycle do you think they benefit most from coaching and what kind of coaching at what, at what stage.
Charlie O'Donnell (21:35)
I read a really great coaching article. I need to find the author. And I feel like it was a New Yorker article about a surgeon and a surgeon. turns out that surgeons peak at 40 roughly because you have accumulated enough hours under the knife. But then at 40, your eyesight and hand steadiness starts to decline. Right. So 40 is sort of the peak of, of surgery as opposed to like baseball is year 27.
Daniel Stillman (21:52)
Wow.
Mm-hmm.
Charlie O'Donnell (22:05)
And the surgeon was like, read that somewhere and was not happy about the idea that he had peaked. And so he tried to figure out how to optimize. And he went out and looked at all of the world's top performers. And the one consistent thing that he noticed is they all had coaches. And he was very curious about what's happening with coaching because like Novak Djokovic doesn't need to be told how to play tennis.
Like his coach is not as good as him in tennis. What are they doing? But they're reflecting back and observing. And I think at any stage of the game, somebody can reflect back at you and ⁓ observe your habits in a way that people are not good at figuring out what it is that they're doing, where their success comes from. ⁓
Daniel Stillman (22:38)
Mm-hmm.
Charlie O'Donnell (23:00)
And this is all across the board. It's not just in their job. Like I'm currently fascinated with ⁓ how complex my life has become now that my wife and I have a kid. And it's like being a manager for the first time after being an individual contributor. And we have a marriage counselor because of course we do.
Like this is the most complex undertaking of any kind of relationship, right? And why would I not want someone to reflect back at me all my communication quirks, limitations, and all of this sort of stuff? We are, I believe we are in a, I don't know if we're top quartile, but we're...
Daniel Stillman (23:36)
Yeah.
Charlie O'Donnell (23:54)
You know, getting there in terms of our communication skills and all of that, with the help of someone who can reflect back at me. I'll tell you a quick story and I know you got to wrangle me around this, but when I finished the book, I, first thing I did is I emailed the final copy to my wife and it took, just a few days went by, maybe a week and I didn't hear anything. And I said, what do you think? Any feedback? And she said, no, I didn't start reading it yet.
Daniel Stillman (23:56)
Mm.
No, this is great.
Charlie O'Donnell (24:23)
And I was really upset. And she goes, no, of course I'm going to read it. You know, it obviously doesn't come out until April. I got, I got some time. I was like, so upset. And I said, I've been working on this thing for six, eight, nine months, whatever it was. And then you're the person in the world that I most want feedback from. And, and we had this discussion with our, our, our therapist. And she said, why didn't you just tell her you wanted her feedback right away? Why was it important for.
Daniel Stillman (24:23)
you
Charlie O'Donnell (24:53)
her to assume that. I said, well, it's clearly obvious to anybody. Like, why would you not? Like, and I was so dug in that I was right. And then the therapist said to me, is there anything that your wife expects you to know that you wish that she would just tell you? And I was like, yeah, how much time do you have?
Daniel Stillman (25:03)
Hmm.
Hahaha
Charlie O'Donnell (25:20)
And I just having that reflected back and be like, ⁓ I am clearly doing to her the thing that, that, you know, she does to me or vice versa, right? This is literally the mirror thing. And it totally changed my, I'm not going to say totally I still feel like I'm right, but it's still my perspective on it. And it is so that's what I'm doing when I'm coaching. I am just like, you told me your goal was X and let me just reflect back at you what I see.
Daniel Stillman (25:26)
Mm. Yeah.
Charlie O'Donnell (25:49)
Being a mirror is, I think, most of what I am doing in that. Occasionally I drop in a, I still have strong opinions. I'm not a totally objective coach because I know the people, I know the ecosystem, but I try to be a mirror for the person's own goals and I try and help them be accountable in that way.
Daniel Stillman (26:09)
Yeah, it's a fine line. Edgar Schein has this book called Humble Inquiry, where he talks about this tension between asking and telling because in a way, we're all nobody likes to be told what to do. Generally speaking, we like to be asked. And and yet sometimes I think when it's in all of us is somebody who just wants to be told the right answer.
Like there's got to be a secret. I'm I'm messed up and I'm confused and and I I don't know what to do. Can somebody just give me the handbook? Like, can I just read Charlie's book? Can I can I grind it up in a smoothie and drink it and make it part of my body and just do the right thing? But that is not how that works, everyone. ⁓ We should put a warning on it. Warning, do not eat. ⁓ But there's this temptation to give somebody the answer because you have answers, but those answers are from the past.
Charlie O'Donnell (26:49)
I would not recommend doing that.
Daniel Stillman (27:05)
Whereas a lot of these people are certainly with founders are going someplace where there is no road and they kind of need to find their own path. And it's, but it's, it's, I think it's a delicate day. least that's my coaching approach. And it sounds like you're trying to walk that line too, between being a mirror and knowing that everyone benefits from hearing what they said and saying, is that right? And they go, no.
or saying, I meant to do that and then I didn't. So that's reflection about like intentions and the gap between intentions and reality. think everyone does benefit from that. So that's, it's really interesting to hear your perspective on that. And I really appreciate you reflecting on this story about communication and intentionality. Cause one of the things I wanted to talk to you about was co-founder relationships. I've been doing a lot of research. I've been interviewing co-founders on my podcast for a while now, because I think you say this in your book, it's a multiplier. If you're aligned.
and a time bomb if you're not, which I think is like the quote of the year or the understatement of the year, a little bit of both. And so I want to talk about multipliers because I've definitely there's literally a Reddit thread where people are like, no fucking way. Go your own. Hire everyone you need. Like don't dilute. Use AI. And other people like, yeah, but there's no that price you can put on someone caring as much as you do about this thing.
and you can't pay someone to bring all that juice at the early stage. So like in your practice, how have you found it to be a multiplier to have a have a co-founder?
Charlie O'Donnell (28:44)
So there's lots of things that need to get done in a startup. One of the most important things is that you need to survive it emotionally. And if you don't do that, it's going to be really hard to execute in a sales meeting and, you know, all of that. And having a partner in this is incredibly helpful from an emotional perspective.
Daniel Stillman (29:01)
Mm-hmm.
Charlie O'Donnell (29:13)
right, somebody who is as on board and as bought in as you are. that, you know, because the other thing is I think like, you obviously need to build a team. Even in the age of AI, I think it is helpful to build a team, but that does not mean that anybody on the team has to be your co-founder. So that's often is sort of a tricky like.
Daniel Stillman (29:27)
Hmm.
Hmm.
Charlie O'Donnell (29:38)
Do I need a technical co-founder? Like there are many instances where I'm like, well, you may need somebody technical on the team. Do you want to make them your co-founder? Are they appropriate for a co-founder is actually a different question. That's a different. Right. And that's someone that you really need to be on the same page about emotionally values wise, somebody who has a sense of ownership around the company and all of that kind of stuff. And so.
Daniel Stillman (29:53)
Mm.
Charlie O'Donnell (30:08)
Having that is really incredibly important. The other thing is somebody who also feels like they're an owner is willing to push back, right? Because ⁓ a really good co-founder doesn't think they're right. The really good founder doesn't think they're right all the time. And oftentimes they're only right six out of 10 times or just marginally right. ⁓ And I think it is really hard when...
Daniel Stillman (30:18)
Mmm.
Mm.
Charlie O'Donnell (30:36)
you are a paid employee to tell the CEO, this is not the right path here, but your co-founder can do that.
Daniel Stillman (30:44)
Yeah, this seems like when we're talking about why having a team or a co-founder, even in the age of AI, even in the age of AI, when you can hire a million agents and where you can do so much on your own.
having a person who cares as much as you do about the vision and the product, who's actually willing to call you out on your bullshit unprompted, because you have to tell the agents criticize me. And they won't let you close the laptop and walk away if you don't agree with them. That seems like the real advantage in even in the age of AI as a person who cares, and who will disagree with you when you're wrong.
Charlie O'Donnell (31:30)
specifically
in the age of AI, right? Because I think Claude's not as bad as ChachiBT, but ChachiBT is constantly telling me how insightful I am and how smart and yeah, and no matter how many times I sort of prompt it to be like, don't just, I don't want that, right? It's not helpful. is people can do that. And by the way, most people who aren't,
Daniel Stillman (31:42)
Accurately, of course.
Hmm.
Charlie O'Donnell (32:00)
as economically incentivized as a co-founder, ⁓ probably won't do it because they feel like supporting you as a founder is keeping your confidence up, is giving you a pat on the back and saying, this is exciting, this is great, all of this sort of stuff. they, nobody likes feeling like a jerk. And ⁓ you know, your co-founder, we're well past that.
You know, we both been jerks to each other at different, you know, stages of this company and, and you're, you're, there's a certain sense of honesty that is a requirement of a co-founder that is really integral to the relationship.
Daniel Stillman (32:28)
Yeah.
That's beautifully said. You know, one of the things I think is interesting. A while ago, I had a friend of mine who works with startup Reno on the podcast, and he said that if he sees co-founders who are a 50-50 split, that means that they haven't had the hard conversation. On the flip side, I've seen how when somebody is much, much smaller percentage, there's this, there can be this resentment that builds. And so it's clear that we have to lean into the conversation about who is
gets what, how much. If it's equal, it's it's not accurate because usually someone started first. was their idea or somebody's done more like it's never equal. But it's clear that we have to have that difficult conversation. If you were to write a list of the questions, if you're not you're not Claude, but it's like, write me a conversation guide to help present to prevent a disastrous co-founder divorce.
through a long-term buildup of resentment from unresolved issues. Because that's the time bomb, I think, that you're talking about.
Charlie O'Donnell (33:53)
So I think one of the things that you hear a lot in the startup ecosystem is that financial plans are BS, right? And putting together startup financials is sort of an exercise in fiction or science fiction or fantasy. And I actually think they're a really good anchor for conversation.
This is where we are leading the company. This is the plan. is, you know, the power of the purse in this company is where we are going to be spreading our resources. This is what we expect. These are our goals. These are the people that we're going to hire, all of this sort of stuff. A serious board-like meeting, I think, forces everybody to really be on the same page, right? So if one
Co-founder believes that you should be more of a consumer product and has a consumer background. And the other co-founders like all in on the enterprise sales or what have you. Well, the answer is in the plan actually. Does it have us hiring 10 AEs or does it have us spending a ton of money on Instagram and you know, and Facebook, right? And so making sure that everybody like signs off on a plan.
In the early stages, to many people, feels like overkill. When I used to write term sheets, I would include, I want to be a board observer. And people are like, we don't have a board. was like, actually you do. You're on the board and your co-founder's on the board. I want to have a meeting where we treat this like an adult company. Where we talk about what we're going to do next month and what we did last month and did it work? Did it not work? And we have a serious conversation.
Daniel Stillman (35:24)
Mm.
Hmm.
Mm-hmm.
Charlie O'Donnell (35:49)
You know, Matt Blumberg, ⁓ who was the CEO of Return Path for a long time, like when he, at the beginning of the company, he wrote an HR handbook. Okay, this is literally within the first couple of months of the company existing. And in the handbook, he put in that anybody who was at the company seven years can take a six month sabbatical and return to their jobs. Which like on one hand, this is crazy thing to do.
Daniel Stillman (36:06)
Yeah.
Charlie O'Donnell (36:17)
you would think like, what a waste of time for a two month old company.
Daniel Stillman (36:20)
Yeah.
Charlie O'Donnell (36:22)
Matt was
the first person at the company to take a sabbatical after seven years. I think there was a, right? Seven years he wrote, he literally wrote it, right? I think there is a non-zero correlation between companies that take future planning that seriously and companies that have a future actually, that you spend that much time sort of, you know, planning the operations of the company that it isn't just this
Daniel Stillman (36:27)
He'd been waiting.
Hmm.
Mm-hmm.
Charlie O'Donnell (36:51)
we start up shit show that actually execute on it, right? And so I think that like having a source of truth where your employees can sort of point to like, this is the plan, this is the budget, this is the thing that that's what eliminates the harboring resentment, the uncertainty, the like, I don't know where this plan is going.
Daniel Stillman (36:56)
Yeah.
Charlie O'Donnell (37:20)
And I've even seen it in later stage companies that sometimes like I had a company was forced into a level of uncertainty because they ran into some financial issues. And at the same time, their VCs for just outside esoteric reasons were nickel and diming them on funding the company. They're like, well, you know, we'll give you this and that'll bridge us for three months and then we'll do this other thing. And the company never got certainty over their future.
And morale just fell off the table. Like the marketing person couldn't budget. Like things went south in that company because there was no plan. And I come back to like, what is our plan? Give me the piece of paper that somebody can point to and argue with. Because if it's just how I feel versus what you feel, like that's kind of a recipe for co-founder disaster.
Daniel Stillman (38:15)
Yeah, it sounds like you're talking about disciplined product thinking because we can look at those two hypotheses, define them as hypotheses, define the riskiest assumption, and then figure out how to test the riskiest assumption. And I really loved your how to run an efficient, thoughtful meeting, a seven point plan, have a hypothesis that you can state what we did to test them, you know, what were the inputs and efforts were, what the outcomes were.
What did we actually learn? Can we do we know? What are we going to do about what we learn differently? And like open questions like I could understand why you'd want to be at that meeting because then there's a real conversation that's talking about conversation design that is actually turning this morass this this this question of like, what are we where where's this going like hustle, hustle, hustle to a series of disciplined, thoughtful conversations that
that anybody could participate in and potentially offer support, advice, help, reflection and coaching because it's clear what's going on versus like, whoa, wait, what are we talking about here, guys? Like, are we having this fight again?
Charlie O'Donnell (39:29)
And by the way, mistake that people who are trying to break into startups often make is they think that to go from being a corporate employee to a startup employee, they have to be flexible. That the rigidness that they experienced in their corporate life, you approach a startup and you say, well, what do you do? And it's like, well, anything you need.
Daniel Stillman (39:52)
Hmm.
Charlie O'Donnell (39:58)
you know, when they'd sort of imagine that that's what a startup is looking for. A startup is looking to tame the chaos. They don't like the chaos, right? They want somebody who comes in and says, I do a very specific thing that you need. Like you have been selling by the seat of your pants as a founder led sales. And I am going to figure out what the hell you've been saying to customers.
put it into a messaging strategy that can be taught to AEs and ⁓ BDRs and a VP of sales. And then I would go hire that person and I will take you the hell out of the sales process so that we can actually scale this thing. And that is what I do. And if you don't want the one thing that I do, then like go move on to somebody else. like those people are enormously helpful to...
Daniel Stillman (40:41)
Hmm.
Charlie O'Donnell (40:51)
For example, technical founders who have no idea how to build sales team and feel like somebody who came in with that structure is like a lifeline. thank God. Because you will turn this thing that I've been doing with a Google sheet and God knows what my eight versions of the PowerPoint say. ⁓
Daniel Stillman (41:04)
Mm.
Charlie O'Donnell (41:16)
and bring some order to this chaos so I can feel like I work at a normal company and have a normal job one day because that would be what success feels like.
Daniel Stillman (41:24)
Yeah. Yeah. All right. Well, I know our time is growing nigh. I have a couple more things I want to hit on. And one of them was you mentioned one of my favorite books, which is finite and infinite games. I read that probably when I was a late teenager. And I feel like there's two types of people, people who have read finite games and people who haven't. I'm curious how it came into your world and how it affected you broadly.
I don't know where it exists in your pantheon of books, Charlie. Like, you know, here's the book that I think everyone should the two books that Charlie wishes everyone would read. That's definitely one of mine.
Charlie O'Donnell (41:56)
No.
So quite late actually, and it's because I sort of got reconnected with someone who, a founder, Nama Moran, who built a company called Cheetah. And I have like a steel trap memory for pitches and LinkedIn profiles, basically. I, you know, once terrible with names,
Daniel Stillman (42:29)
Hmm.
Charlie O'Donnell (42:33)
⁓ But once I sort of figure out somebody will come up to me and they'll be like, because I've met a lot of people over the last 20 years, hey, I pitched you this thing and I'm like, drawing a total blank, right? And they'll start to go into what the company was. And immediately I'm like, ⁓ right. You're the guy who used to work at the magazine company and then that thing and then you did this other thing and blah, blah, blah. I know exactly who you are.
Daniel Stillman (42:58)
Mmm.
Charlie O'Donnell (43:01)
I could literally see your LinkedIn avatar and there's like a forest in the background or whatever shit's going on, right? And they're like blown away. And I just maybe have spending way too much time in LinkedIn. But like, Nama came in to pitch us a company when I was at Union Square Ventures and she is no longer at Cheetah, a hell of a roller coaster ride around it and...
Daniel Stillman (43:08)
Wow.
Charlie O'Donnell (43:31)
kind of burned out of it. And she posted about founder burnout and an effort that she was putting together. And I reached out to her and I was like, I'd love to talk to you about this because I have been thinking a lot about work life balance and I'm not a full time VC anymore. have a four and a half year old.
Daniel Stillman (43:43)
Hmm.
Charlie O'Donnell (44:00)
The half is really important. And, you know, I just think like we should chat. And we have a series of really absolutely wonderful conversations. She's like truly a terrific and thoughtful and insightful person. And she considers herself kind of a gamer. And for her, one of the things about a startup is you're sort of constantly writing the story and
And, you know, it's not just about like winning and done, but opening up new worlds and unlocking new things and growth and this very abundance mindset of being, you know, a founder. And so I had heard the book, but I hadn't read it. so I wound up picking it up. And there was just so much in there about people's approach to entrepreneurship and.
Daniel Stillman (44:27)
Hmm.
Hmm.
Charlie O'Donnell (44:57)
even approach to small problems, right? Like so many people want to know, should I do this thing or should I do this other thing? And, and the answer is actually like, invent a third way or, or, you know, create something new that doesn't lock you into just this, this binary outcome. And, ⁓ and so it, it, I think it is really useful to have sort of an abundance approach philosophy to this, particularly in like,
You think about venture where people think of this as false binary choice between should I bootstrap this and run a cashflow lifestyle small business, or should I swing for the fences and bet everything on this and, and, you know, take all the investment money in the world? It doesn't have to be like that. Right. It could be creatively financed and seed strapped, if you will, and run for.
initial like, yes, I need money to help me get to product market fit. And once I do that, you know, I have some element of control and I'm going to go for a cashflow and maybe I'll buy my investors off the cap table with a really nice return and continue to run it for a long time. Like there's all sorts of options that you don't have to get locked into and you can, you know, continue to, to play. mean, I'm reminded of,
Anthony Castellana, who was the founder of Squarespace, bootstrapped Squarespace with a very small loan from his dad early on. I think he told me it was like 20 grand or 30 grand. was like literally paid for him to just survive for like six months while I coded that thing. And he was like, he had no employees for like the first six years of Squarespace as a company before it started to grow and he started to build and started to hire. So he
Squarespace lived a bootstrap lifestyle business life until it really took off. And then he got an acquisition offer. And he said, you know, it was never about the money until somebody put a figure down that I owned 95 % of. And all of a sudden that was a very distracting number. And I couldn't stop thinking about it. And then I went out and I engineered a round in which I was able to take some money off the table.
Daniel Stillman (47:06)
Mmm.
Charlie O'Donnell (47:17)
And he, he raised like out of nowhere, people didn't realize how big the company had gotten, like a $38 million round. I don't know how much I haven't get a guess. Maybe he took half or 40 % off the table. And he said, I immediately bought an apartment closer to the office. Put the rest of the money in the bank and never thought about it again and went back to work because I had lots of things that I wanted to do at the company. And ultimately they became an IPO. And it was just a really great.
Daniel Stillman (47:42)
Yeah.
Charlie O'Donnell (47:46)
approach to like, I don't need to do it the way that everyone else suggested. I'm going to do it at my own terms and at an appropriate stage and do what I do successfully. And I think it's a great approach.
Daniel Stillman (47:52)
down.
Yeah, that's the that's really treating it like an infinite game, like where there's no winning or losing. There's continuing to play. And I think, you know, it makes me think about a founder who I was coaching, who was going to have been really driving on their company for a long time and felt like they just weren't going to get to the IPO stage. They were they were tired.
And that IPO, they had held that as the finite game. Like if they don't get there, then they're really not going to be successful and their dad's not going to really be proud of them. you know, this immigrant, some child of immigrants makes good. And they got to the point where they were like, you know what? An aqua hire is fine. I want to incubate my next three ideas. I have two young kids. I would like to just start investing in my relationship with my wife and
pivot. And which brings me to my I hope you still have time for my last question because you were this essay that you wrote that I was just on your newsletter. I didn't even know you were working on a book where you wrote this essay about what's next after losing somebody's money. I think this is such an interesting infinite game view of this world.
Charlie O'Donnell (48:56)
Yeah, right.
Daniel Stillman (49:15)
A venture capital viewed not as a finite game of like I got money and you know, I raised and I built an IPO. It's like, well, actually. The more likely thing that's going to happen is it doesn't. And so how do I design that conversation? Do I go, do I disappear? Do I ghost? Do I go hat in hand and say, ⁓ I'm sorry, I blew it. Your essay, thought was very good.
You you have kind of a script to say, listen, this is I own. I'm going to own this. Here's my critique. I wonder what your thoughts are. And, you know, here's maybe what I might be working on next. Like, how do you think about coaching a founder to enter into that conversation with the infinite game mindset?
Charlie O'Donnell (50:05)
So one of the things I really like about being a, nobody calls it a blogger anymore, a newsletter writer. You this is the thing when you've been writing in this format for like 22 years, I used to be a blogger. I don't know what it is now. And it's that I can have these real time conversations. And that essay literally started the moment after I got off the phone with one of the founders that I had backed, whose company had failed.
Daniel Stillman (50:35)
Hmm.
Charlie O'Donnell (50:36)
And the reason why I was on the phone with them is because somebody asked me for a reference because he's starting something new. And I was put in this very awkward spot because I didn't know he was starting something new. And what am I supposed to, I don't know anything about that. What kind of a signal is that? ⁓ you know, I guess, I guess they're on bad terms now because they're not even talking about, you know, what the next thing is. And I said to him, I was like, I don't think that's what you want me to say. I have no idea what he's working on.
Daniel Stillman (50:46)
Hmm.
Charlie O'Donnell (51:05)
or the implied like, maybe I don't care what he's working on. I'm not interested because he's proven to be such a failure. I said, this is going to signal for all sorts of things. And he kind of admitted to like, I feel like I couldn't pitch you on it because of the fact that he had lost the first time around. And I told him, said, well, listen, and I really love, and a couple of them are in the book.
Daniel Stillman (51:15)
Hmm.
Charlie O'Donnell (51:34)
the sort of four quadrant, know, one of two things can be true and then the other two things and the variable can be true. And that's, makes the sort of a four box thing. Either I think you're a loser or I don't. And you either come and talk to me about it or you don't. Right. And you sort of explore the four boxes. Like maybe I think you are, but if you come and talk to me and you own it, my reference might be.
Daniel Stillman (51:53)
Mmm.
Charlie O'Donnell (52:03)
You know, that was really a S**T show, but I think he's learned a lot. And I feel like, you know, earnestly trying to, you know, not repeat the same mistakes. And, you know, I really appreciate him. And I would certainly think more of him for, you know, approaching me along those lines. ⁓ Maybe it doesn't change anything about the way that I think about it. Well, you know, there's nothing lost there, right? You're not going to make me feel worse by coming to me and saying I learned something, right? But if you don't.
Daniel Stillman (52:08)
Hmm.
Charlie O'Donnell (52:34)
then I'm liable to say anything, right? I've never backed that guy, what a jerk, know, whatever. But the reality is, I think he worked his ass off at a company. I think there were some things that were hard. think there's some things you could probably do better. He should want to know what those things that I probably thought he could better at, right? And so to get that feedback, I think is...
Daniel Stillman (52:52)
Yeah.
Charlie O'Donnell (52:57)
is really important. ⁓ And that's one of the reasons why I've always tried to be really transparent with my investors, even in the fund. ⁓ I had somebody come to me and say, you seem pretty even-keeled. How are you doing this? You're managing all this people's money. I said, well, first of all, I acknowledge the fact that maybe I'm not good at this. I try. I work really hard at it. I ask for help. But
Daniel Stillman (53:21)
Hmm.
Charlie O'Donnell (53:25)
I'm not going to tie up my identity with I am a good VC and that's what kind of a person I am. Because if it turns out that I'm a bottom quartile performer in all of my funds, then who am I as a person? Like what a terrible outcome that would be. But there are people who definitely feel that way. And it's undoubtedly depressing. And so I tell myself that I am trying hard.
Daniel Stillman (53:41)
Mm.
Charlie O'Donnell (53:54)
And that there are certain things in my control that I should do better. That's one of the reasons why I like being a coach is it gives me a positive outlet to deal with all the mistakes I made. You know, I can go back and be like, dude, I have a really great idea for a mistake that you shouldn't make. And then somebody would be like, that's awesome. I won't make that one. As opposed to me just being like, you know, a mistake I made. what an idiot. And I, there's nothing positive there, but now I can turn all my mistakes into.
Daniel Stillman (54:15)
Mmm.
Charlie O'Donnell (54:22)
positive advice for other people.
Daniel Stillman (54:25)
I mean, that's what that essay is, is somebody who really did not give you the opportunity to be prepared for the reference. I also appreciate the sort of the game design approach of, it's one of these four things. And if they think you're an idiot and they don't want to talk to you, that's just the one of the four things that you can't do anything about. That's not in your control. But most of the options involve you talking to them and moving the needle somehow.
on their perspective and also, as you say, getting that opportunity to get more information back from them. ⁓ You know, I do have I drew this funnel that you talked about on Tuesday, like I'm to see 2000 companies a year, I'm going to talk to 150 of them, I'm going to research 20 of them, and I'm going to fund 10 of them, like which are very hard numbers. And you talked about how the founders have this sort of positive mindset, and they need to have this, I'm going to jay curve this thing and I'm one of
one in a million. This is a one in a million ideas on the on the fear and greed scale out of you. There's so much you should be terrified for not going to taking advantage of this opportunity. And there's so much money here. You got to get involved. I think it's challenging to maintain optimism when when you know that most of the companies you're looking at are going to fail. And I'm wondering, because you do seem like you present as somebody who is.
I mean, self-reflective, but not morose. You don't strike me as an Eeyore. How do you maintain your sense of optimism and enthusiasm for all these pitches you've seen knowing that, you you're in the infinite game, but most of them are going to somehow going to lose.
Charlie O'Donnell (55:52)
You
Daniel Stillman (56:08)
Was this something you learned at your parents knees? Is there a book you read? Or is it just how you're built?
Charlie O'Donnell (56:17)
What the first question I need to ask myself is, would I consider myself optimistic? And.
I don't know if being optimistic is being anti pessimistic. I don't have to think about that because I'm not a hundred percent sure that there are always, that there are always opposites. And I say that because I'm like, I always push people to think, is it possible that you could win? Right?
Is it optimistic? Because I know they're a long shot, but I focus on what's possible. Right? And so I know going in that for every 30 companies I invest in, my hope is that three of them drive most of the returns. I mean, I hope they all drive most of returns, right? But, but
The math works if three of them are driving most of the returns. The thing I do know is every single company that I've ever invested in had a possible path to blow out success. There's not a single company that I invested in. I couldn't tell you these are the ingredients for this team, this idea to win. Right. So was always possible. ⁓
Daniel Stillman (57:43)
Hmm.
Charlie O'Donnell (57:48)
I think I always am realistic about the chances and how hard it was. So I think I mentally prepare myself for what could happen beforehand and that makes it easier. I think that, I mean, in some case that does come from family, but ⁓ maybe in a, you know, sort of a difficult way. It's like, I've experienced a lot of ⁓
dealing with family health issues. ⁓ My mom was sick for quite a long time. ⁓ My dad went through a ⁓ CNS lymphoma and went from like being totally fine to being gone in like six crazy weeks. And in each of those moments, I felt like I had to step up as a, you know, sort of take on burden as being like local son and, you know, tag team this with my
siblings. And the way I would sort of approach it or even deal with it is to be really realistic about, ⁓ here's what we might be facing here. You know, like, just let me think through all of the possibilities. I don't want to be surprised by anything. And then once I've like acknowledged the worst thing that can happen, being like, okay, I mentally prepared myself for all of the bad things that could possibly happen.
Nothing's going to be surprising here. Now let me just go forward and the best way that I can possibly do that. and most often the worst thing that can happen is not the worst thing that actually happens. So you're like, that's not as bad as it could have been.
Daniel Stillman (59:21)
Hmm.
Yeah.
Right. Yeah. If we're doing the four box, it's like best case, worst case, best case, worst case, like the odds of the worst, worst case and the best, best case. You've gamed it out and you're prepared for the other. The others and say, like, look, I'm prepared. I'm prepared. You're a prepperist, it sounds like.
Charlie O'Donnell (59:50)
Yeah. Yeah, I'm
a little bit of a prepper. think, yeah, I probably am a bit of a prepper in that case. More so than that. Comes with its own sort of, you know, yeah, yeah.
Daniel Stillman (59:55)
I would call you a prepperist. It's a little classier than a. Yeah. Yeah. Tinge, let's say.
So listen, I think we're definitely in time. I appreciate you ⁓ making this time, Charlie. Is there is there anything I haven't asked you that I should ask you besides what I'm going to ask you afterwards, which is where can people find more about your work? And, you know, we'll put it all.
Your the links to all the your things in the show notes, but like what aren't people you're doing a lot of these So what what have I not asked you and what haven't been people asking you that you think people should be asking you? What's the unasked question?
Charlie O'Donnell (1:00:36)
You know what I really appreciate is that every conversation I've had about this has been slightly different and comes at it from a different perspective. And I think part of the reason for that is that the book is written for the 99 % of people who are going to struggle to fundraise or for whom fundraise is not just a slam dunk, right? Who didn't just sell a company for half a billion dollars and now clearly everyone who backed them before is going to come back again, right? That is most people.
The ways in which you could approach that process are infinite. It is how do you have the emotional fortitude for it? How do you build a team? There are so many different podcasts and conversations that I could have around this. Talking about venture, right?
Daniel Stillman (1:01:25)
Hmm.
Charlie O'Donnell (1:01:31)
I talked to a law class and while it was an entrepreneurial law class, it was very clear that this was a place where there was a lot of interest in public interest and small business entrepreneurship and all of this sort of stuff. And we talked about a whole variety of factors that go into this. So every conversation is unique and having a discussion.
that focuses on what kind of difficult conversations that people have and what is underlying, you know, about partnership and all this sort of stuff is great and it's interesting and it's complex. yeah, you have asked different questions than just about any other person has asked and that's what makes this fun. It's also is one of the hard things about writing a book is that
Daniel Stillman (1:02:04)
Hmm.
Charlie O'Donnell (1:02:28)
by definition is incomplete. Right? And I've gotten some feedback around some of the things I've been writing about lately of like, well, you talk about what, you know, underrepresented founders go through and you talk about it from the founder side and that's really incomplete because it's really all, yeah. Yeah, it is because a completely exhaustive conversation is impossible, right? So yeah, it's based on...
Daniel Stillman (1:02:31)
Yes.
It would be exhausting, honestly.
Charlie O'Donnell (1:02:56)
Yeah, yeah, totally, totally. So ⁓ no, I appreciate the line of questions and there's nothing glaring that is left out.
Daniel Stillman (1:03:09)
Excellent. Well, that makes me feel good. We can always come back. We can do a part two. Well, speaking of part two, is there another book that you feel like you're like, okay, now I know the book that I want to write next? Is there something like itching in the back of your head? Because clearly you are ⁓ writing doesn't seem maybe there are hard parts of the book for you to write. But this it seems like writing is something that's really a muscle for you. That's well trained. Yeah.
Charlie O'Donnell (1:03:09)
But if I think of it, we can always come back and do this.
I like writing.
I really do like writing. And I don't love book writing. And I don't love book writing because of the sort of finality of it, the point in which like it is done and you can't add to it. And I know there's like additions and updates, but it feels like monolithic on-premise software, you know, versus, you know,
Daniel Stillman (1:03:41)
Hahaha!
Charlie O'Donnell (1:04:00)
Claude comes out with a new feature every day and it's amazing, right? And I love being able to have a conversation and immediately turn it into a blog post slash newsletter and to go back and say, I wrote this thing and actually I was wrong about it or whatever. The fact that this book, I closed the book on it literally five or six months ago and it just feels like I'm so paranoid that it's.
Daniel Stillman (1:04:03)
Yeah.
Mm-hmm.
Charlie O'Donnell (1:04:28)
feels totally inadequate in the face of the progress that AI has made. And I feel like I need to create an addendum that is like how to manage your fundraise with AI and all of that sort of stuff. And there's plenty of YouTube videos about all of that sort of stuff. So it's fine that it's not complete in that way. But the two topics I'm most interested in going forward is I am really fascinated with how parenting changes relationships.
I had its impact on that. you know, lot of my coaching clients, a few of them are having their first kids or getting pregnant or whatever. you're such a dad, you constantly, you know, talking about your daughter. Tell me parenting tips. was like, I don't have any parenting tips, but the thing I do tell people is there are eight and half billion people on the face of the earth. The parenting thing is relatively straightforward. It's hard.
Daniel Stillman (1:04:58)
Hmm.
Charlie O'Donnell (1:05:26)
But like, you'll figure it out, like, cause people have figured it out. How it changes your relationship is no one really talks about. And how all of a sudden you picked this person to be the most important person in the world. And now you are neither's most important person in the world is really difficult. And, and, and, you know, I think that's really fascinating. And then the other is if I wasn't a VC and if I wasn't an investor, the other thing I could have done in life, although I'd be severely underpaid for it.
Daniel Stillman (1:05:43)
Yeah, yeah.
Charlie O'Donnell (1:05:56)
is to run a career planning office in a university. And I find that job really fascinating. And I think it is no more challenging than it is today where you have graduates joining a market where entry level jobs are getting obliterated by AI. There's no company loyalty. And yet the world is their oyster. And I would just tear all of that shit out and completely
Daniel Stillman (1:06:00)
Hmm.
Yeah.
Charlie O'Donnell (1:06:25)
redesign how we teach kids to be entrepreneurial and all of that sort of stuff. ⁓ that's probably what I would write about. And that was what my first book was about, but no one's ever seen that book because I wrote a book a couple of years after I graduated and I shopped it around to publishers and nobody cared who I was. And it was called Start Strong, Graduate Great. And it was all about how to find a job you like in college.
Daniel Stillman (1:06:27)
Hmm.
Charlie O'Donnell (1:06:54)
actually get into it and at some point I'll write a modern version of that probably.
Daniel Stillman (1:07:01)
Or just put it into a resource augmented ⁓ file and just make a chat bot for the kids to talk to. Honestly, Charlie, it's very humbling because it's a strange time to be alive always, but it's a real challenge. And I think you're...
Stochastic probabilistic based like a Preparist view of the world while balancing up like an optimistic visionary view of the world is something that ⁓ It sounds like your kids lucky to have a dad who thinks that way they won't always they won't always think that but Well, listen, I'm really grateful for the conversation this is great stuff where should people go
Charlie O'Donnell (1:07:35)
I think she's just happy I like ice cream as much as she does. That's where her mind is.
Daniel Stillman (1:07:50)
Obviously, obviously they should read first buy founder unfriendly follow you on.
Charlie O'Donnell (1:07:56)
I'm on Squarespace. so I have been at thisisgoingtobebig.com forever. That is my website. There is a link to the book there. Obviously it's on Amazon. It's on bookshop.org where you can go buy from your independent local bookstore.
and it is a very findable title. That's probably the first title we even considered. And as soon as it popped into my head, everybody really liked it and thought it was fitting for my personality. Buyers of the book, not that it's very expensive, but if you really want to get high ROI from it, can email their receipt to founderunfriendly at next, n-e-x-t dot n-y-c.
And we will invite them to a series of eight conversations that we are having with co-founder of Data Dog, co-founder of ZeroHash and MoveableLink and Backupify and ⁓ the Wing and just like all these really terrific founders that have seen the ups and downs of being entrepreneurs. We're going to do those conversations May and June. ⁓ So it's really going to be a fun set of conversations with people I've worked with.
Daniel Stillman (1:09:03)
Mm-hmm.
Charlie O'Donnell (1:09:09)
and ⁓ share it and give it to you. If you feel like you're an expert and you feel like you're in that 1 % who didn't have trouble fundraising, you know someone who needs this if they are thinking about being entrepreneurial. And even if it means opening a coffee shop, you still might have to ask for money for someone. And my hope is that it is still useful to that person as well. So I appreciate it.
Daniel Stillman (1:09:34)
Yeah, yeah
Yeah, I think it is useful for all those people Well, okay That's all great stuff. I think you've been more than generous with your time. And so I will call scene I will
Charlie O'Donnell (1:09:46)
There you go.