Family Office or Index Provider

Family office roles can be hit or miss. I've written about them before and people seem to appreciate the insight, so I'll say some of the same things.

• No two offices are alike. Two family offices in the same city with the exact same asset base and launched in the exact same year probably look really different on the inside. One may follow the allocator model and have the majority of the wealth committed to external fund managers. The other may be a hodgepodge of random direct investments like the ones you described; no real rhyme or reason apparent.
• The air can be thin. There's little room to hide when you're one of just a handful of non-family members working there. You may feel like you've got nothing to do half the time, and the other half, you don't necessarily enjoy what you do spend time on. Without the fog of a larger organization, it's harder to blend in and look like you're throwing yourself at things while actually taking it a bit easier.
• There's often a cult of personality. Whether it's the principal making all the decisions him/herself or the CIO they hired, there's almost invariably one person who calls the shots, decides who gets what title, how everyone spends their time, what the investment focus is, and what the culture is like.
• Recruiting opportunities are wide and diverse. Other family offices love the seal of approval and will hit you up directly. Recruiters will message you with opportunities at other offices in random geographies that surprise you. Fund managers will cold email you because they want to develop a relationship and get a dollar commitment from your office. Those same funds will want you to join their IRBD team under the logic that you probably know several other family offices besides the one you're at. Wealth management arms of big firms will be down your throat routinely trying to get you to move over - you know how to interact with highly sensitive, highly wealthy, highly discreet people.

I could go on.

I recommend that you stay there for two years total. You will have the freedom to punch your ticket at whatever type of role interests you as long as you put the work in to develop the network. The perception is that you are in a highly desirable role. Don't throw away that ticket without milking it for all it's worth.

No one will ever know how disorganized things really are under the hood. Whatever you tell someone about your experience is what they're going to know. It's actually the norm that you be pretty limited in what you're able to disclose when speaking about your experience.

If you want to go back into venture, spend a month making a map of every strong fund you'd feel lucky to work at. (I'd recommend avoiding the massive franchises like A16Z and looking for the leaner places that aren't too top-heavy. Like Acrew, August, or if you're aiming at New York, places like RRE, GC, Spark, Thrive ... )

Then email people there, explain you're at a family office, you have a wide-open mandate and the direct ear of the principal, and that you're interested in whatever-stage deals in whatever-industry. Like Series A and Series B fintech, automation, and the future of work.

Get calls with all these people, start trading the stuff you're reading and seeing with them every couple weeks, and build a relationship. If you do this correctly, you should get to know a couple dozen people at really strong firms who begin showing you their deals. They're doing an $8m check and the total round is $12m, prior investors are doing $3 of pro rata, so there's a $1m slug. You get the deck and show it to your boss, add as much context as you can from your research on the space, brag about the firm and how strong they are in venture, and try to get him to do it.

Hopefully over a year or so you get two to six of these things done. If you were talking regularly to all the people you met (and that should include the founders of the companies you're looking at, anyone they introduce you to, people you hear are great resources for specific functional or sector knowledge, etc.), you should have a huge network in venture.

If you alert them to the fact that you're thinking about a next step, several of those funds you've now got friends at should be asking what your plans are. Be really alert here: these are 'soft' conversations in that very few will flat-out say "Hey, you want a job here?" It will look more like "Oh, congrats, that's a great update, what sort of things are you thinking about pursuing?"

You say "Well, you know I've always focused on early-stage enterprise software in fintech and automation, so my ideal is a firm with a bi-coastal presence, good fund size so there's great ability to do follow-on rounds in the winners in the portfolio, and people whose lens I really respect." You basically feed the description of their own firm to them. You'll eventually hear enough of an opening where you can ask "Do you think it makes sense to talk to anyone else on your team?"

Obviously tailor this to each firm you're speaking with. Also, don't have wildly divergent stories going with different people. It's a tiny industry. You don't want one firm hearing that you want early-stage enterprise and another firm hearing that your destiny is to do growth-stage consumer. When I say tailor, I mean speak about all the soft stuff: intimate partnership, flat culture, bi-coastal reach, portfolio support initiatives, all that jazz.

If you want something other than venture, follow the exact same methodology. Draw up the list of who matters to you. Begin speaking with them. Get them to traffic what they see with you. Cherry-pick the best of it to convince your boss to deploy into it. Down the road, speak to those people about an opportunity to join them. Or if a golden ticket falls in your lap and a better family office wants you to move over, even better.

I'm sorry you found it so disorganized. It's pretty common, unfortunately. The position you've inadvertently found yourself in really works for someone who's a strong self-starter. That may feel really unfamiliar to you, but it's a valuable muscle to begin flexing.

Think about it. You aren't getting fired. Your boss isn't around enough to even know whether you're doing well or not. Business sounds like a hobby for him more than a necessity, so he's looking for excitement, something compelling. Capitalize on that by doing a few months of work to set up a machine that begins delivering you gems that you can polish really well before putting them in front of him to hopefully pick up.

He isn't there to teach you a proper diligence framework, the end-to-end deal management toolkit, scalable sourcing mechanisms, or anything that would be really valuable in an associate role. It isn't ideal. However, if you find a way to level up on one or more of those dimensions (I just gave you a crash course in sourcing), you will stand out head and shoulders above your two colleagues and probably get a few things done during your time there. That makes you highly marketable. If you want to leave the family office space, you can do it from a position of strength. If you want to stay in the space, you just have to find a different place. So many offices have the same problems you're describing here. If you prove you're the man with a plan and can execute on it, you're money-good.

Also sorry your prior role was a shitshow. Sounds like a Binary Capital type of story.

Good luck.