My Year of Giving Dangerously

Just over a year ago, I embarked on a crazy experiment: I wanted to see if I could make a living by giving. Not investing in startups, not donating a portion of my time and money to a cause, just giving. After reading Adam Grant’s book, Give and Take, last summer, I decided to take the “Give First” idea espoused by Adam, Brad Feld, David Cohen, and others to its logical extreme. I would give first, second, and third, then give a little more, without requiring any equal trades in return, and see what happened. I wanted to see if Adam was right, that people respond to generosity with generosity, that the majority of “matchers” in humanity want to lift givers up while bringing takers down. I’d already seen what takers could do and I was not impressed. Now I wanted to see what a giver could accomplish.

Spoiler: it’s a lot.

As I’ve done with similar activities, I established some ground rules to make this easier to both explain and carry out:

  1. As long as I could make the time, I would say “yes” to anyone who asked for my help or advice. I expected that this would mostly be related to building a tech startup, but if someone wanted help packing boxes and I had time, I’d do that too.
  2. My advice and experience were free, period. As long as the other person left with the to-do list, then I would never charge them for my time and advice. I didn’t want anyone to stop asking for help because they were afraid the meter was going to start running.
  3. If someone asked me to own something, then we could talk about payment. Consulting was now my livelihood, so at some point someone was going to have to pay me. If I took on the to-do list, then I would charge for my time or — if I ever built one — my team’s time.
  4. If I had to “sell,” I was out. I have great respect for those people who can make cold calls, work the room at a networking event, and somehow get permission to show up at someone’s office and pitch goods and services, but I simply can’t do it. Before I took the first step on this journey, God and I made a deal: no “selling” to people who weren’t interested. If doing this meant that I had to become a hustler, then I would rather work at Starbucks. I hear they have a great health plan.

I started in mid-August serving one small paying client and helping nine companies for free. By mid-September, the paying client had canceled their engagement, but I was meeting with twelve people at least every other week: advising them on their business ideas, helping them figure out how to build their first minimum viable product with little money, or counseling them as they tried to manage people for the first time. I heard some great ideas and some terrible ones, met some really smart people and had coffee with some “very stable geniuses” who definitely shouldn’t have quit their day jobs. In each case I tried to find a way to help, even if it was to gently suggest that someone should consider addressing a few of the gaping holes in their business plan before asking friends to invest in it. In each conversation, I tried to listen as much as I talked and to learn as much as I taught.

In each conversation, I tried to listen as much as I talked and to learn as much as I taught.

September and October were hard, both financially and emotionally. I found one or two small engagements of a day or so, but no other money was coming in. After each coffee meeting, that Starbucks application beckoned from the counter. The stress of helping others when I had no income of my own took a toll, and I lost sleep wondering how I was going to pick up a second college tuition bill in the coming fall. From that perspective, the experiment was not going well.

On the other hand, the non-financial rewards were growing. People I had already helped were starting to send others my way, and I was now advising companies in New York and Silicon Valley. I joined Michael Lopp’s rands Leadership Slack group and found a whole community of technologists trying to lead people for the first time. With my abundant free time, I was able to offer help and advice both online and off, and I continued writing articles about the patterns I was seeing in technical leadership struggles. I was up to meeting 15–20 people on a regular basis, with some one-time online question-and-answer threads on the side.

Another interesting thing was happening: the mentoring conversations were going deeper. Where we started out talking about product/market fit, financial models, and the cost of hiring engineering talent, we were now talking about the emotional strains of running a startup. We swapped stories of sleepless nights and awkward phone calls asking family for money. They talked about impostor syndrome, their worries that they would never figure out how to lead people, their fear of failing and letting down the people who had entrusted them with their money. I shared my own experiences with those fears and assured them that it could get better. I offered advice on dealing with difficult employees and ordered people to take a couple of days off and sleep.

Where we started out talking about product/market fit, financial models, and the cost of hiring engineering talent, we were now talking about the emotional strains of running a startup.

We went beyond simple conversations in coffee shops, too. I joined a “packing party” for a book subscription company and helped fill over 250 boxes with gifts, tea, and personalized book selections. Then I went home and redesigned the assembly line because the inefficiencies were killing me. The next time, we did 325 boxes in 2/3 of the time, although I’m not sure we had as much fun. I helped a pair of founders split amicably one week and listened to the tale of woe from a CEO who fired his CTO and saw his whole engineering team walk out the next. I helped someone avoid getting fired while telling someone else that it was time for him to leave his company before it crushed him. In each conversation, I coached and I learned. What I didn’t do was profit.

Then came November. As Thanksgiving approached, I was grateful to know that I had made a small dent in the perpetual misery machine that is the startup world, but I was wondering exactly how long I could keep it up. I’d received plenty of encouragement and bewildered looks from the people around Boulder and Denver who were watching my experiment, but not a lot of revenue. Two big engagements that would have funded a small team apiece were perpetually on the horizon, but like a mirage in the desert they receded as quickly as I pursued them. Experience told me that the holiday season was a dead time for sales and starting new projects, but if I didn’t start making some money by the end of the year I was going to have to give this up. Starbucks beckoned.

“You’ve gotta talk to Jason. He’ll help.”

That’s when a phrase started repeating around me: “You’ve gotta talk to Jason. He’ll help.” It started with a longtime friend in Boulder who came across a small company that needed a product built. They only had a couple of people, but more importantly, they had a budget. The project started small, but since I’d spent the last several months helping early-stage companies figure out how to build on a tight budget, I was ready to beat all comers on price and quality. Then a CTO who’d watched me wandering around the area helping everyone I came across did some wandering of her own, right into the office of a new arrival in her co-working space. As they talked, the other woman, who was CEO of a seed-stage tech company, mentioned that she was about to lose her product lead and needed someone to rebuild her engineering team and her product. Here came that phrase: “You’ve gotta talk to Jason.” A couple of weeks later, I had my first fractional CTO gig.

As the year renewed, so did my hopes for this experiment. My cobbled-together team of contractors was building one product, then two. As part-time CTO I was building another team and defining a new product, and I was able to use my new contacts to find good engineers when I needed them while helping quality development shops grow. I found other people who shared my mindset about going above and beyond to help startups grow, and I saw an ecosystem of giving start to develop around the work we were doing together. I also saw people who I had helped decide to “pay it forward” and share their experiences and skills with others who needed them.

Of course, startups are still startups. Several companies that I was mentoring shut down, occasionally with my help. I offered support, advice, and job-hunting referrals for those founders, and I attended the last packing party for the book box company right before Christmas. We drank a toast to the end of a dream while hipster Christmas carols played on the Bluetooth speaker, then we hugged with tears in our eyes before loading up the last shipment to go to the post office. Their customers would get one last gift before Christmas, but they were on their own in the new year.

We drank a toast to the end of a dream while hipster Christmas carols played on the Bluetooth speaker, then we hugged with tears in our eyes before loading up the last shipment to go to the post office.

Things picked up quickly after that. Requests came from further and further away, while the phrase echoed through an expanding network, “You’ve gotta talk to Jason….” I got the opportunity to work with a wide variety of companies, from doctors using AI to improve emergency room screening procedures to crypto enthusiasts trying to help Belgians pay their bills with Bitcoin. Over and over, I talked with young CTOs who realized that, even on the bleeding edge of technology, the technical problems are the easy part. It’s the people who make things complicated. With each conversation, I saw the power of complementary expertise: I learned from these people who were experts in machine learning, medicine, cryptography, and smart devices, and in return I taught them how to leverage technology for competitive advantage, to build a business, and to lead a growing team without self-destructing. Because the Venn diagrams of our respective expertises barely touched, we each sounded like a genius to the other and grew smarter from every exchange.

Because the Venn diagrams of our respective expertises barely touched, we each sounded like a genius to the other and grew smarter from every exchange.

I was helping people from all over the country, from Austin to Atlanta, New York to California. And some of them were even paying. After coaching one CEO for nearly a year, she finally hired me to find her an engineering team, saying, “I’m so glad that I can finally pay you somethign after all the help you’ve given me!” I became fractional CTO for another company and started another small-team project. I started building a network of other senior leaders who could also take on part-time work leading startups while maintaining the “give first” mentality. And I watched as others took up the mantle, offering guidance in exchange for coffee and lending years of hard-won experience to newly minted CTOs, customer relations managers, and product managers, all in the name of making the startup life better.

It’s been about 15 months since I started this experiment, and I’m extraordinarily pleased with the results. After a couple of lean months, the business side took off more rapidly than anyone could expect, especially considering what you might call the “negative sales” effort on my part, telling people to keep their money if all they wanted was coaching and advice. I don’t know if I’ll ever fully know the impact of the non-revenue-generating side of my efforts, but I do know that I’ve at least made work life a little bit better for more than 75 different startups (and counting), and I’m having a great time doing it.

I had lunch with some friends from a former company last week, and when we were done eating one of them said, “You’re so much… lighter than I remember. You just seem like a huge weight was lifted from your shoulders.” Considering that I’m busier than I ever was when she knew me, with responsibility for several companies on my shoulders, it seems like a strange observation. But she’s right: I feel lighter even while doing more, because I finally feel like I’m doing what I was made to do. It’s counterintuitive, but the more I give the more I have to give. The more expertise I share, the more I gain, and the more people I help the more patterns emerge that can help others. And the more people I infect with this idea of giving to succeed, the more success I see around me. It’s actually working. Empirically, the experiment is a success.

It’s counterintuitive, but the more I give the more I have to give. The more expertise I share, the more I gain, and the more people I help the more patterns emerge that can help others. And the more people I infect with this idea of giving to succeed, the more success I see around me. It’s actually working. Empirically, the experiment is a success.

Here are a few things I learned over this year of giving dangerously:

Generosity is contagious

When I told people what I was setting out to do, I got a lot of puzzled looks. I still do when I sit down with someone for the first time and they ask, “What do you charge?” But once they see it, whether it’s getting help themselves or seeing someone else get it, they want to go do it. For some, it’s a sense of obligation, a debt they have to discharge, so they go find a way to “pay it forward.” For others, giving is a new experience and when they see someone else doing it they think, “Hey, that looks like fun. I want to try it.” They find that they like it, so they do it again. Others see them in action and the cycle continues.

Sometimes, we just need a reminder that it’s safe to give without asking for something in return.

The best conversation opener is “How can I help?”

I am not a fan of conversations with strangers. Drop me into a networking event and, like Bob Seger at a disco, in ten minutes I’ll be late for the door. Hell for me would be a roomful of people with business cards, and I have to get every one before I can find salvation. So how do I keep finding myself standing at the door to a coffee shop waiting to make awkward eye contact with someone and ask, “Hi, are you Bob?”

It’s because now it’s not about me.

The hard part of every conversation is trying to figure out how to bring it back around to you. When you’re listening to someone while simultaneously trying to nudge the conversation back to your issues, your product, your sale, you’re having at least two conversations at once, and (at least for me) it’s exhausting. But when you sit down and ask, “How can I help?” and then you spend the rest of the time actually trying to help, well, that’s only one conversation, and it’s fully engaging. You bring the best of yourself to the experience and put it at the disposal of the other person, working to solve their problems and make their future better than their present. That’s energizing, and I can’t get enough of it. And so despite my best introverted tendencies, I keep meeting strangers and asking, “How can I help?” And I love it. I strongly recommend that everyone try it.

You bring the best of yourself to the experience and put it at the disposal of the other person, working to solve their problems and make their future better than their present.

Everyone has time and genius to give

As I’ve gone on this journey I’ve taken every opportunity to bring others along with me, and along the way I realized something amazing: no one ever says no when you ask them to share their expertise with someone else. In fact, they love it! Several people, when I asked them to mentor someone I’d met, said, “That’s the first time anyone has ever called me an expert. Thank you.” Recognizing someone else’s genius, then asking them to share it, is a validation of all the time and energy they’ve put into their work, and it shows them that they have something valuable to share with others. We’re often afraid someone will be too busy to help, so we don’t ask. Meanwhile, they’d be honored by the request and glad to find an hour every week or two to mentor a new member of their field. So the next time you meet someone who’s struggling with their job, think about someone you know who does it well, then introduce them. They’ll both thank you.

Several people, when I asked them to mentor someone I’d met, said, “That’s the first time anyone has ever called me an expert. Thank you.”

Everything comes back around

This whole experiment was built on the idea that people respond to generosity with generosity, lifting givers up even when they aren’t the direct recipients of their giving. I will firmly attest to the truth of this theory. Almost without exception, my paid work in the last year came, not through someone who had benefitted from my coaching and mentoring, but from someone who’d seen what I was doing and wanted to help me. In some cases, they didn’t even think they were sending business my way; they just saw someone who could benefit from talking to me. They said, “You’ve gotta talk to Jason,” and the next thing I knew I had a new client.

God and I kept our agreement: I’ve never had to hustle to get business this year. I’ve just gone out and helped people, and one way or another, people have helped me in return. Now when someone asks me, “How can you afford to do all this for free?” I shrug and say, “I just do. Somehow, it all works out.” Generosity is not only contagious: it’s reflective.

Generosity is not only contagious: it’s reflective.

This Thanksgiving, my family went around the table saying what we were thankful for. When my turn came, I said, “I’m thankful that my giving experiment turned out so well. We have truly been blessed this year.”