How to find the right people.

And how the right people can make all the difference.

By: Sebastian Marshall, Executive Director at GiveGetWin

The GiveGetWin Summer Camp 2016 attendees and team at the Polsky Exchange at UChicago

You can get a lot done by yourself, but nowhere near as much as you’d get done with a great cofounder, a great team, great mentors, and a great ecosystem around you.

The head of YCombinator, Sam Altman has written that things get done through a mix of focus and having great people in your life. We’ll examine his second point —

On the personal relationships part, most people eventually realize it’s hard to do really good things by yourself — most of them just require too much work … It’s easy to not spend enough time on personal relationships — it seems in conflict with focus. But it’s an important exception. It’s also one of the most enjoyable parts of work.

Some people reading this already have a lot of great people in their lives supporting them, and working together in great harmony — but if you don’t yet, how do you make it happen?

Strategy #1: Project Partners

One of the best pieces of advice I got from an older and established mentor —

“Don’t look for a business partner. Look for project partners.”

Starting a business with someone, that you actually want to succeed and commit to, should be done with the same seriousness and deliberation as marrying someone. A company that gets initial traction will take at least a couple years of your life to see if it has legs; if it goes well, it’ll take 7+ years to run the gains out and make a success.

Your cofounder will be one of the most important people in that timeframe; you’ll often spend more time with him or her than with your family or friends. If there’s friction, conflicts, or any unpleasantness between you, you’re at critical risk of failure.

I personally believe it’s impossible to know how well you’ll collaborate with someone from only socializing with them. We all have different styles of working, getting things done, resolving conflicts.

As such, it’s highly recommended you take on project partners— people you do small, intense projects with, to see how well you work together.

This can be as small as hosting a board game night for friends or a small dinner together. It’s really that simple. Just find someone who you like and who you think might work well with you, and ask, “Hey, you want to host a dinner together and each of us invite half the guest list?”

Even something as small as holding a dinner teaches you a lot about working with someone.

Volunteering at a local civic organization, organizing an event, planning a weekend camping trip, getting on a one-month training plan at the gym together, taking a short road trip… any of these can be seen as quite small projects. You learn a lot about how someone relates to punctuality, responsibility, communication, conflict resolution — even from these small things.

If it doesn’t work well, nothing lost. But if it does work well, you’ve got something to build on.

Strategy #2: Trust Cycles

I strongly recommend you start with the smallest possible projects, and work with many people to see how you relate with different people.

A project isn’t and shouldn’t be as complicated as the Normandy Invasion — if you’re at UChicago, you might plan to drive up to the beautiful University of Wisconsin-Madison Campus to see an event there. You’ll learn a lot about someone from it.

There’s no reason you can’t run 20+ very small projects like this in the next three months with people. (If you don’t know anyone at all, see the next point.)

But once these go well, then what?

Gradually do a series of slightly bigger projects. This builds into “trust cycles” — you get to know someone in situations of progressively more responsibility.

If you planned a single-day event, you could go on to plan a series of four events. If you worked on a single science paper together, you could try collaborating on a simple open-source science tool.

The goal is to get into upwards trust cycles with people with whom you have a natural compatibility .

Strategy #3: Luck Surface Area

If you don’t know people with whom you already want to do projects, you will want to increase your luck surface area — the number of random people that you meet who you think have the potential of doing meaningful work with you.

Overwhelmingly, the easiest way for young people to do this is through conferences, hackathons, and similar multi-day events where a lot of people are gathered for a common purpose.

Almost all university campuses now host events like this, and the vast majority are very open to students from other institutions and non-students attending. When it comes to conferences and hackathons, the best way to get involved is to participate as much as possible.

When you’re wearing a “staff” or “volunteer” badge at an event, you’re having a very different experience. You’ve got jobs to do and you’re in work mode — people are seeing you contribute and perform, and you’re meeting others in the same capacity.

Do as good of a job as possible, even if it’s clear the event won’t be a major force in your life going forwards — this drives at the next point, track record. Meanwhile, look to get to know other people and what they’re doing enough that you can stay in contact and propose one of those simple quick projects as project partners to start kicking off the trust cycle.

Strategy #4: Track Record

The best people to work with are those that can get things done cheerfully, elegantly, and are enjoyable to be around.

To work with those types of people, you’ve got to be one of those types of people yourself.

Track record is thus twofold — first, fully commit and take serious every project you take on, from the big to the small.

Second, document your successes in a public way.

Strikingly.com (by UChicago / YCombinator alum David Chen) is a great free tool to make websites quickly and easily. You’ll want to put together a Strikingly or some other sort of portfolio website that can display pictures, accomplishments, and testimonials that say you’re great.

UChicago alum and venture-funded entrepreneur Greg Nance has a great simple Strikingly page: note, Nance iterated his many times — you don’t have to be that “complete” out of the gate. Just get one started, adding accomplishments to it, as well as photos and endorsements.

Your track record is what will convince great people that you’re worth working with, and will encourage established mentors to bet on you. Commit to excellence in all your projects, and start documenting your track record online yesterday.

Strategy #5: Great Mentors

Great mentors will greatly accelerate your success.

Most people don’t realize it, but it’s incredibly easy to get great mentors.

Here is a process that reliably works:

  1. Ask for concrete advice.
  2. Ask clarifying questions to make it concrete, but do not argue their advice. Ever.
  3. Thank them.
  4. Implement their advice promptly.
  5. Follow up and let them know that you implemented their advice, and say thank you without asking for anything else.

That’s it. That’s all you need to do to get great mentors. If you do this regularly with established people you admire, they’ll happily take your emails and eventually your calls reliably.

Most people don’t ask for advice. They often argue or get defensive if they don’t want to do what they’re told or don’t like what the advice was. They don’t say thank you. And, they often don’t take the advice or follow up at all.

If you simply follow those steps, you’ll be ahead of around 99% of people in winning mentors over. After that, it’s similar to project partners and trust cycles — you can reach out for more advice, or propose a (very small) collaboration a few weeks later, and you’ll likely get an enthusiastic response.

To choose the right mentors, pick (1) people who have accomplished what you want to do, that (2) you genuinely admire who (3) ideally understand how you think.

The first two points are essential: you should select someone that’s “been there” since their advice will be hyper-practical, and admiration is critical. For instance, if you’re very punctual and you can’t admire a mentor who is good but often late, you should look for another mentor. Almost all people can sense genuine admiration as well as disdain, and your best mentors will always be someone you admire.

It’s also beneficial but not quite essential that they understand how you think. For instance, if you’re a programmer who wants to be CEO of a tech company, it’s beneficial to have a mentor who can code and has been an executive — it means they understand how you think. A more sales-driven CEO might not relate to your skillset, so definitely seek out mentors who “get” how you think.

So, where do you find these mentors?

Same as before: go to conferences and hackathons, increase luck surface area, and build a track record that makes you look like someone worth remembering. You may know you’re awesome — but you still have to work to convince others.

Also, a lot of top entrepreneurs love to give back and often have “mentor sessions” or office hours. The Polsky Exchange at UChicago has amazing mentors and there’s consistently bandwidth for open mentor slots. As part of the larger Polsky Center, membership to the Polsky Exchange is free for UChicago students, and a bargain at $150/quarter for local entrepreneurs. There’s consistently great people doing mentor hours there — these are people who (literally) would charge $200 to $1000 per hour if doing consulting, that’ll meet with you for free to pay it forwards.

Beyond that, there’s tons of opportunities like this in the world. Sean O’Sullivan, who founded MapInfo, coined the term “Cloud Computing,” and now runs the $250M fund SOS Ventures, offers free 15 minute spots just to talk to entrepreneurs a couple days a week. (Full disclosure: I co-invested in a Shanghai startup and serve on its board with SOSV’s China Managing Director, William Bao Bean. I note that example because very credible people are often willing to meet you for free — if you just look up the times and places they’re happy to mentor.)

A lot of people won’t seek out mentors out of shyness or a sense that “they should be further” ahead, but that’s nonsense. Just do it, a lot. To get three amazing mentors who really want to bet on you, you’ll likely need to meet 10–20 people, ask for advice, thank them, follow the advice, and follow up. It takes a trivial amount of time relative to the huge gain for your life.

To summarize and conclude…

It’s a great time to be an entrepreneur: there’s more resources, proven processes, and ways to de-risk entrepreneurship than ever before. It’s no longer a crazy and illegible bet, but rather a proven path you can walk.

To build a career in entrepreneurship, you need the right people in your life. We discussed five strategies, which you can start applying right now:

1. Look to do small projects with project partners. You can easily do 20 of these in the next 3 months, as small as a simple road trip, hosting a dinner together, or writing a paper together. Even the smallest project lets you see if your natural working styles are in harmony. When you find someone you like and admire, ask them to do a very small project together — the smaller and shorter the project, the better.

2. For the projects that go successfully, get into an upwards trust cycle with those people: do more, slightly bigger projects. This lets you test how well you’d work together on a more permanent basis.

3. To get more people into your life, increase your luck surface area. If you’re just starting out, the fastest way to get there is by going to conferences, hackathons, multi-day events like Startup Weekend. If at all possible, work to be a full participant — don’t just go to a conference as an attendee, work behind the scenes to set it up and make it happen.

4. Build and demonstrate a track record. The best people want to work with people who already succeeding and doing. Take every small project you do very seriously, and document the successes on a simple website builder like Strikingly. This makes it easier to get into projects, increase your luck surface area, and collaborate with more successful and veteran people over time.

5. Find great mentors. It’s shockingly easy: find entrepreneurs who want to give back through a university, accelerator program, or people who just like to help young people. Ask for their advice, don’t argue with them, thank them, take the advice, and follow up saying you took the advice — without asking for anything else. If you follow this process with 10–20 people you admire who have had success in the field you want to succeed in, you’ll easily wind up with three great mentors. This can all be done easily in 3–6 months.


Sebastian Marshall is Executive Director of GiveGetWin, a nonprofit with a focus on innovation in philanthropy and engaging young people in a way where volunteering turns into immediately useful life skills. GiveGetWin team members regularly run events and trainings at the top universities such as UChicago, MIT, and NYU Stern.

Marshall is the author of four books on productivity, history, and applied math, including Gateless, a guide to managing one’s intangibles for young people on the rise. He writes one free long-form essay with actionable lessons from history at TheStrategicReview.net

Sebastian’s background is in enterprise sales, growth, operations, and scaling in high tech and finance. He occasionally angel invests (time permitting!) does what he can to help young people going up in the world.

Feel free to reach out to him at sebastian@givegetwin.com or come to a free event across many top campuses in the USA on the next GiveGetWin Tour — tour.givegetwin.com