Long Journey Ventures backs founders it calls the “magically weird.” The firm works out of a Victorian house in San Francisco, its corporate values page lists its Dungeons and Dragons alignment as Chaotic Good, and another value instructs the team to “be a bubbe,” the Yiddish word for grandmother. It would be easy to mistake the whimsy for a lack of rigor, until you look at the track records. Partner Cyan Banister came out of Founders Fund, and she and Venture Partner Scott Banister spent more than twenty years angel investing together in SpaceX, Uber, PayPal, Anduril, Postmates, and Niantic. Somebody has to keep a fund like that compliant, audited, and running on time. That somebody is Dani Tustin, Long Journey’s first employee and as of 2026, CFO.
Welcome back to Office of the Venture CFO, our monthly series with the people actually running finance at top venture firms, presented by Juniper Square. Last month we sat down with Mike Witkowski at ENIAC Ventures, who came back for a return visit that covered AGM prep and how to manage the vendors who help you manage your fund..
Dani came to venture the long way around, through law school and years of partnership tax work with emerging managers. She told Long Journey cofounder Lee Jacobs “no” the first time he came asking, then called him back a few months later with a change of heart.
The following content is for informational purposes only and should not be construed as personal legal, tax, investment, or financial advice. The transcript below has been edited for length and clarity.
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From Supreme Court Ambitions to GP Tax Questions (That Weren’t Actually About Tax)
Venture5: Your background is different from most of the people we talk to. Let’s start pre-venture.
Dani Tustin: I was one of those nerdy kids who decided in eighth grade that I wanted to be a Supreme Court justice, and I kind of stuck with that path, meaning I ended up going to law school. I went to UC Hastings, here in San Francisco. And I got there, and I was like, now what? What do I actually like? I found myself gravitating toward classes that were a little more business-oriented. I’m not the most adversarial person, so the litigation side of things was not super appealing to me. All of the business lawyers I talked to said make sure you take a lot of tax classes, because tax is going to be a huge factor in every business decision that gets made, and it’ll give you an upper hand. So I took my first tax class and loved it. I had a little bit of a mathy brain but also this lawyer side of me, and it was just a beautiful combination.
Venture5: And after law school?
Dani Tustin: I ended up working in tax at Andersen, primarily with different types of investment funds in the alternative investment fund group. Partnership tax is really complicated. There’s a lot to know and a lot to learn there. Most of my clients were either venture capital firms, PE, or fund of funds, but really my bread and butter was the emerging manager scene here in the Bay Area, through the 2010s.
Venture5: So a lot of smaller, newer funds.
Dani Tustin: Lots of fund ones, fund twos. I also worked with some larger, more institutional, older funds. But I really liked working with the newer funds because I was usually working with the GPs directly. They didn’t have a CFO or a controller. And GPs are an interesting breed of human. They would ask me questions thinking they were tax questions, but they really had nothing to do with tax. So I found myself in kind of an advisory position with a lot of these emerging managers on their fund ones. “Who should I use to bank? Who’s a good fund admin? How should I set up my portfolio tracking?” Because they didn’t really know who else to ask.
“GPs are an interesting breed of human. They would ask me questions thinking they were tax questions, but they really had nothing to do with tax.”
How She Was Hired
Venture5: You were employee one at Long Journey. What does the hiring process look like for employee number one?
Dani Tustin: It definitely was a long process. Lee Jacobs is one of our founding GPs, and he and I have known each other for going on fifteen years now. We ran in similar ecosystems. When he went out and launched his first institutional fund, which is Long Journey, he actually came on as a client. He was one of those emerging managers who would call me at random hours and ask random questions that were definitely not tax-related, but I didn’t charge him, so it was better than him going to his lawyer. We had a beautiful working relationship and kind of kept tabs on each other.
As they were going out to fundraise for their second institutional fund, he started to poke around. “Would you leave?” “Do you know anybody?” Those sorts of things. And I was super happy at Andersen. I loved the job. I was a year and a half away from making partner. So it was, “No, I’m good, but I’ll keep my ear to the ground”.
Fast forward a couple of months, and I had this epiphany where I was like, actually, do I want to be a partner at Andersen? I looked at the life and the lifestyle of the partners there and how stressed they were every time new legislation came out, and all the different things they had to go through. I realized I wanted something different for my longer-term career. I called Lee two days later and said, “Hey, have you found anybody?” I think I ended up actually starting five months later.
Venture5: In those intervening five months, what kind of questions were you asking to vet the opportunity?
Dani Tustin: For me, I really didn’t want to get super shoehorned into finance. I have a more varied background, and finance is something I’m really interested in and enjoy, but it’s not the only thing I enjoy. I helped grow the team I worked on at Andersen. I was one of two who started that team, and now there are fifty or sixty people on it. I was there through employee thirty or so. So I was really curious about what the future looks like. What does future headcount look like? Where do you see this going?
And then, after seeing lots of fund ones and fund twos not raise their next fund, a certain amount of homework on the partners and their track records was in order. A big part of it was that, to an extent, I felt like I was getting married again. Entering into this business partnership where I wanted to grow, they wanted to grow, and are we going to be able to support each other mutually and really watch the firm flourish.
Venture5: If you were counseling other CFOs looking at joining a new or newer fund, what would you tell them to ask?
Dani Tustin: I would really try to get at how long of a leash you’re going to get. How much do the GPs really want to be reviewing wires and getting into the quarterly financials, or is this going to be a relationship that’s built on trust and allows you to be much more strategic? I know several CFOs whose GPs want to oversee every aspect of finance. That’s just a really tough relationship to be in. So really trying to get at questions on autonomy, and how to build that trust, is super important.
And then the GP’s vision for how the role will develop. I’d want to hear a lot around, “we want this person to be really strategic in helping us think through portfolio construction, and pacing, and GP positions.” Because ultimately you want to do more than just close the books every quarter.
“Ultimately you want to do more than just close the books every quarter.”
Venture5: And on the track record, which you mentioned was something you dug into. What do you want to be cognizant of there?
Dani Tustin: It’s a great question. I was lucky that they were willing to give me the same materials they had given their LPs and prospective LPs on what the firm had invested in, valuations, industries, all of that. One of our partners, Cyan Banister, has a very long track record and a lot of notoriety in the venture community, so hers is pretty easy to just Google. But with Lee, it was really looking at discipline. One of the things Lee is really great at is relationship building with founders, and becoming that phone call. He would back a founder and then back them again and back them again and back them again. That commitment to the founders was huge for me.
I was also looking at the companies themselves. These are companies I’m going to be working with. I’m going to be talking to their founders and their CFOs. I’m going to be talking about these companies to our LPs. Are these super boring SaaS companies that I’m not going to be able to explain, or are these interesting businesses that captivate my attention? I did care quite a bit about the fact that they were investing in interesting things.
The First Ninety Days, Starting With a Late Audit
Venture5: In the early days, were there things you wanted to get a handle on very quickly, versus things that could wait a few months?
Dani Tustin: One hundred percent. I joined in late April. Our audit was due April 30th and it wasn’t out. So the number one thing was, let’s get the audit out the door.
Beyond that, we basically had a fund admin platform, a CRM, and an Airtable that was kind of the source of truth on our portfolio. So it was really building out that Airtable to make it much more systematized, rather than just a list of companies. Who are the co-investors? How much did we invest? What’s our ownership now? Really building that out as my source of truth for what has happened historically.
Venture5: What else did you build early?
Dani Tustin: A pacing tracker, to help keep the GPs on top of where we are in our deployment period. That was something I sensed we needed, because we have three partners internally and four venture partners who actually do make investment decisions. So let’s keep track of this and keep the investment team apprised of where we’re at within our portfolio construction and deployment period.
Venture5: Other CFOs have told us pacing is their job to keep an eye on, but you’re the first to say you actually built a tracker for it. Tell me how it works.
Dani Tustin: I took our portfolio construction and simplified it into a single sheet, and then kept a running list next to it.
It was pretty rudimentary at the time, which was really all that I needed. It could tell me something like, “We’re a year and two months into our deployment period, we should be at X percent deployed in our core checks, and whoa, we’re twenty percent higher than that.” Alert alert alert. We either need to slow down, or get ready to fundraise a little bit sooner, or consider writing smaller checks. What are the ways to rectify outpacing our model?
Over time I’ve been able to automate some of that, and now I have a beautiful pacing website that any of the partners can access at any point. Thanks to Claude, of course.
Portfolio Construction Is a Tool, Not a Bible
Venture5: Given your legal and tax background, does that cause you to go deeper in certain areas, or less far into the weeds than someone without that background might?
Dani Tustin: I don’t know that there’s anything tax or law-specific. With portfolio construction models, it’s all about the assumptions you’re putting in there. Meaning, yes, this portfolio construction that we’re presenting could play out as a 5x net fund, and here’s a way to get there. Most likely that’s not the way that we’re going to get there. It’s going to be another way. There’s going to be something hopefully great that happens, or three great things that happen along the way.
But the model of how you’re going to get to whatever returns is all based on historical assumptions. What percentage of companies raise Series A’s, and what’s the dilution they take. And who knows. The AI world is so crazy right now. The prices of rounds are insane. There’s no way you could have modeled that accurately three years ago.
So I like to use the portfolio construction as a source of truth for what we want our portfolio to look like. But then you have to take it with a huge grain of salt, because all of these assumptions are just that. Assumptions, based on things that are one hundred percent going to change. For me it’s getting out of the weeds of the numbers, making sure things tick and tie, and using it as a tool as opposed to a bible.
Venture5: So guidelines, not rules.
Dani Tustin: Exactly. And there are going to be exceptions. The lawyer in me sometimes struggles with that. This is what we said we were going to do, why are we doing something different? And Long Journey has really taught me to roll with those exceptions. Some of those exceptions have been our best performing companies.
Venture5: Does the portfolio construction go down to the partner level, or do you look at it at the fund level?
Dani Tustin: We definitely have to take that into account. There are certain partners who deploy at faster paces than others, and it’s something we have to continue to re-evaluate every six months or so, because it also depends on the areas they’re interested in. There are just a bunch of different factors. But it mostly is fund level, with a few people in particular who are higher volume, I’ll say.
Venture5: So the model respects the unique preferences of the individual investors.
Dani Tustin: Yes. At least for us, because partners can act on their conviction to an extent, it’s important to build that in.
What the Voting Data Said About Their Best Companies
Venture5: I know firms do this differently. Is there voting? Can one person just put something through if they have conviction?
Dani Tustin: We kind of have two different types of checks. We have our core checks, which require three votes from the investment team. And then we have solo conviction checks, and those are smaller, anywhere from $100,000 to $400,000. We call that our Wayfinder program. We watch those companies, and hopefully at some point there’s an opportunity to increase that position to a core check, assuming the company is doing well. But our core bets do have more consensus.
Venture5: How did you land on three votes?
Dani Tustin: One of the big projects I did, three years ago now, was to come in and review all the historical voting data. And we found that our best companies had more consensus internally. They may have been very non-consensus among other venture firms and other investors, but internally, a lot of them had three or four votes. So we implemented this voting system where in order to get a core check done, you need multiple votes.
“Our best companies had more consensus internally. They may have been very non-consensus among other venture firms and other investors, but internally, a lot of them had three or four votes.”
Venture5: That’s super interesting, because a lot of what you read when a firm talks about their big winners is that those companies were very divisive internally. It sounds like the opposite.
Dani Tustin: Well, they still may be divisive. As long as you can get three votes. It’s funny that you say that, because on some of those deals, they got the three yes votes, but there also were no votes. We don’t make everybody vote on every deal, but if you really don’t like something, then you’ll put in a no vote, and we track that.
CFO as Voice of the LP
Venture5: You just closed the fourth fund somewhat recently. Where do you see the opportunities to strategically help the firm over the next few years from your seat?
Dani Tustin: A couple of different areas. The biggest one is definitely along the portfolio construction line, sizing. Really helping the partners figure out what size check we should be putting in at a given point, what fits within our model, what’s right for the stage of the company, and creating a longer-term game plan of what building out ownership in a particular position might look like. Getting more strategic on those follow-on decisions.
There are also areas I hope to grow out around tracking and data, and always improving our methodologies for valuations. We have a really big portfolio, and we’re trying to uphold our fiduciary responsibilities to our LPs. So I’m always trying to find that balance between getting the real information and the investor updates, so that we’re marking companies at the right place.
Venture5: One last question, and it comes from your values page. I love the values page. You have this concept that you’re all Chaotic Good Dungeons and Dragons characters. So what does a Chaotic Good venture fund CFO look like?
Dani Tustin: It’s something I probably would have had a hard time answering back when I first started: what that really means. Independent thinking. But also, I really am the voice of the LPs in the room, and really forcing the GPs to think through that lens, which sometimes means throwing a curveball at the decisions they’re making.
So for me it’s bringing the transparency and bringing the facts, but also being open to things not going along with what is logical, and having to roll with the chaos. It’s super important, being at Long Journey.
About Dani Tustin
Dani Tustin is the CFO of Long Journey Ventures, where she was employee number one. Before joining the firm, she worked in tax at Andersen, in the alternative investment fund group, with venture capital firms, private equity funds, and funds of funds, with a particular focus on the Bay Area emerging manager scene. She holds a law degree from UC Hastings in San Francisco.
