As a startup, one of the most important decisions you can make is ensuring you have access to experienced technical leadership. While hiring a full-time CTO can be expensive, there’s a better alternative than going it alone: the fractional CTO.
Five Years of Giving Dangerously
Five years ago, I began a radical experiment that would change my life: I started a for-profit company built on generosity. I did it because, despite everything I’d been taught from my first days in business school onward, I really wanted to believe that you could be generous and successful in business at the same time.
Note that I didn’t say that I believed this. I wanted it to be true, but I had little proof. In my experience, the takers, liars, and assholes seemed to be the ones who shot ahead at work while the givers overworked themselves into middle management obscurity. “Charity’s for home,” one boss advised me, “At work you take care of yourself because no one else will.” I hated that advice even while acknowledging what seemed to be a hard truth. So that’s why this started out as an experiment: I had a hypothesis that things didn’t have to be that way, but I desperately needed proof.
As I shared here, the first year was both difficult and rewarding, but I was ready to call my experiment at least a partial success. I determined that, at a minimum, I could “give first” in my business relationships and make a living as a consultant. I had also managed to build a small but steady business without doing any “selling” in the traditional sense. I wasn’t hustling for prospects: clients were coming to me, sent by people who had already benefitted from my help. So the answer, at least for me, was, “Yes, you can make a living by giving.”
The answer, at least for me, was, “Yes, you can make a living by giving.”
That’s great, but in the words of every startup investor ever: does it scale? After five years, I think so. Today, Da Primus employs 15-20 people, depending upon our project load, including four fractional CTOs who are helping startups build their products, teams, and companies into (hopefully) successful and growing businesses. We’ve worked with more than 30 clients, usually for at least 6 months apiece, and we’ve advised over 100 more companies for free.
It seems like we’ve gone through every version of the startup story in the past five years: massive growth, steady expansion, acquisition, slow extinction, and fiery collisions with the end of the funding runway. Whether they were growing like weeds or shutting down, we’ve guided our clients to find the path that was best for them, their product, their employees, and their customers. We’ve lived a hundred startup lives, with many more to come.
So what’s the point? Is this a humblebrag “look how we’re growing!” marketing post? Definitely not.
So what’s the point? Is this a humblebrag “look how we’re growing!” marketing post? Definitely not. You see, most people are still surprised by a business plan with two words: Give first. They look at a consulting model that doesn’t squeeze dollars out of every interaction and ask, “How do you make money?” So in a world full of “How I made my first million” and “How I turned my side hustle into $10K/mo” articles, I thought I’d share my tips for how to build a sustainable, healthy business by giving before you get, then giving some more.
And if you leave with nothing else, I hope you remember this:
It absolutely works
It’s a lot of fun
There are two psychological principles at work here.
First, being generous implies that you have resources to spare. Or, as one author put it: “When I behave generously, I feel rich.” Even if your budget was feeling cramped before, when you genuinely give to help another person you open up a source of bounty that you didn’t know you had, so you feel better. From a business perspective, giving freely says, “We have time and money to spare,” which equates to success. Combined that with generosity in your business practices and you have a powerful attractant. Given the choice between two partners, wouldn’t you choose to work with the one that’s successful and is going to treat you well?
The second principle is our innate sense of fairness. Most people naturally want to balance the scales in their relationships and expect others to do the same. When they see someone give genuinely and unstintingly, they feel a sort of karmic debt and want to do something kind in return. This leads them to either “pay it back” or “pay it forward” to settle the debt, which often means trying to help a business that operates with generosity. How many times have you felt compelled to share a moment of exceptional customer service or given your loyalty to a company that treated you well? In a transactional world, generosity stands out.
In a transactional world, generosity stands out.
So how do we do it?
We start with the same ground rules that I established in Da Primus’ first year:
If you have the time, say yes. To requests for advice, for help, to “pick your brain” over coffee. This is our first avenue for helping others, but it’s also a powerful pathway for opportunities.
Our advice and experience are free, period. Taking an hour to point someone in the right direction costs us little, and no one should ever stop getting help because they’re afraid the meter will start running.
It’s all about the to-do list. If we meet with someone and they leave with all of the to-dos, then it’s free. If someone asks us to start owning things, then it’s time to talk about our consulting services.
No selling. All of our business is inbound, solution-driven, and relationship-based. We might hire a business development person someday, but if we do their motto will probably be “Never Be Closing.”
“Hang on, I think I got one of these wrong...”
Beyond that, we’ve developed a few practices that guide our decision-making and make room for generosity in our regular course of business.
Start by helping
Like most technologists, we’re problem-solvers at heart, so framing the correct problem space is essential. Rather than focusing on making a sale or adding people to an engagement, we ask, “How can we help?” Because we like elegant solutions to problems, this leads us to ways that our presence can have an outsized impact on every person we talk to and company we work with. In other words, by focusing on the best way to help, we create leverage for our roles.
We follow this with another question: “If this were my company/budget/idea, what would I do?” By putting ourselves in someone else’s shoes, we create a sense of ownership that helps us make better decisions with them. This often means that we find more capital-efficient ways for them to reach their goals, which builds trust. It has also helped us to build a network of trusted, “startup-friendly” partners who understand that their job is to build companies, not billings. We may not maximize our profit from each project, but we build lasting relationships that lead to repeat business.
Ask “what’s the generous response?” Then do it.
When we aren’t sure what to do, we seek the generous response. Sometimes, this means reducing the amount we charge a client that’s having trouble getting funding or working extra hours to bring a client through an important company milestone. Sometimes it means helping someone see that there’s no new feature that will save their company, so it’s better to spend those last dollars on giving their employees a soft landing when they shut down. Whatever it is, we work toward the best interests of our clients, mentees, and even each other.
When we aren’t sure what to do, we seek the generous response.
Why not just try to be fair? For one thing, fair is subjective and we all consciously or unconsciously try to slant circumstances in our favor, as every contract negotiation illustrates. Also, fair is boring. We want clients to remember and recommend us, so we go further. In the words of Linus Pauling:
“Do unto others 20% better than you would expect them to do unto you, to correct for subjective error.”
Make a Generosity Budget
Being generous might make you feel rich, but if you’re already feeling pinched then it can feel impossible to even take that first step. There’s an easy solution, though: budget resources to give away. At Da Primus, we reserve 10% of our time for free coaching and mentoring (I also put 10% of our gross profits into a Blessing Fund, but that’s another story). This makes it easy to say yes to those requests for coffee and advice without feeling like we’re forgoing profit. Of course we have time to help: it’s right there in the budget!
Budget resources to give away
Being this intentional with our time not only removes pressure when we see an opportunity to help; it also shows everyone in the company that we value their experience. Coaching isn’t just something that senior people do: everyone’s an expert in their chosen field and can use their hard-won expertise to smooth someone else’s path. We want everyone to feel that satisfaction and, hopefully, get hooked on it.
A couple of years ago, I was at a dinner with someone who’s famous for skipping the small talk at work events and asking penetrating questions instead. After warming everyone up, he asked, “What advice would you give your 25-year-old self that would have changed your life for the better?”
I only had to think about it for a moment. Swallowing the lump in my throat, I said, “You can afford to be so much more generous than you think you can.”
And trust me, it’s worth it.
Who Cares if it Scales?
The Poisonous Myth of Hustle
We’ve all heard the story: two brilliant founders have an idea that will change the world. They gather a dedicated group of early employees/stock option holders around them and, through sheer grit, determination, and HUSTLE, they disrupt an industry and become billionaires in the process. The moral of the story: anyone with a good idea and the willingness to sacrifice everything on the altar of Hustle can become a success and the envy of their graduating class at the next reunion.
Except… that isn’t really true, is it? Every year, hundreds of thousands of technology startups fail, and of those that survive only a tiny percentage ever reach unicorn status. And those hustle-filled origin stories? Well, they’re not 100% factual, either: multiple studies and books have shown that luck plays a significant role in every company’s success, and while some founders are willing to acknowledge that fact, our cognitive biases push us toward crafting a narrative where our success was wholly due to our own hard work and perseverance in the face of adversity. So those founding myths skip the part where the brilliant youngsters met the right people or were born to the right parents and they focus instead on how they did it all themselves. “Luck is what happens when preparation meets opportunity!” they crow. But when that opportunity for the big pitch came, were they sharper for having averaged four hours of sleep a night for the past six months? Of course not.
According to myth, Sergey Brin and Larry Page started out manually answering search queries until they could automate the process (photo credit: William Mercer McLeod)
There’s no question that hard work plays a role in every success story. Otherwise, it would just be boring: “He was born rich, he took over the family business, and he coasted along until he grew bored and went sailing.” The Great Gatsby that isn’t. Entrepreneurs start companies because they’re passionate about their idea and they’re willing to do whatever it takes to bring it to life. We should rightly celebrate that and reward it when the idea is successful. This is the American Dream, that anyone can become a success if they work hard enough.
The problem with the Hustle Myth, though, is that it glorifies one element of the story and ignores the rest. Through the hero-making machines of Silicon Valley and social media, the Hustle Myth has weaponized deeply ingrained elements of American culture — the ideal of rugged individualism and the Protestant work ethic — to the point that the only measure of a human is how hard they work. The results are both insidious and poisonous.
The Hustle Myth has weaponized deeply ingrained elements of American culture… to the point that the only measure of a human is how hard they work.
We want to believe that our efforts matter, so it’s tempting to accept the lie that the harder we work the more our success is assured. The problem for a startup team is that the idea that they can win by hustling harder than the big guys is mathematically false. 100 Amazon employees, even giving a half-assed effort, are going to put out more work than the 20 “hustlers” at TinyCo. If competition heats up and both teams work 20% harder, the startup team burns out and Amazon still coasts to victory. Startup success doesn’t come from bulk effort.
It’s bad enough when founders fall prey to the Hustle Myth and work themselves into the ground. It’s worse, though, when unscrupulous leaders use it to exploit their employees. “Welcome to startup life” becomes the answer to long hours, 24/7 availability, and low salaries, all in service to a massive expected payout when the company becomes a unicorn. Anyone who resists these demands or, worse, tries to meet them until they burn out, “isn’t cut out for a startup” and should go back to a safe corporate job. The tech world is filled with stories of leadership teams churning through staff on an annual basis, pumping up each new hire with tales of the exciting opportunity before them while conveniently ignoring why their predecessor left. I’ve seen it in action and it’s sickening.
Leaders: if you’ve normalized weekend work or your team is fighting fires 24/7, that’s not “life in a startup.” That’s a leadership failure.
Don’t get me wrong: there are times when startup life means working some strange hours. That’s the nature of being on a small team and the price we pay in exchange for the outsized impact on a company that makes working for a startup so appealing. If you’re the only engineer who knows how to fix a production problem, then you’re going to need to work the occasional weekend to keep your product running. But that should be incentive to share your knowledge — and therefore the support load — not a weekly expectation. Leaders: if you’ve normalized weekend work or your team is fighting fires 24/7, that’s not “life in a startup.” That’s a leadership failure.
Perhaps worst of all, buying into the Hustle Myth leads to lazy thinking and, for most startups, failure. Here’s how that works:
In HustleLand, time is an infinite resource fueled by the twin magical essences of Passion and Desire. The more we want to succeed, the harder we hustle and the more time we have. Not getting things done in time? Hustle harder!
Since time is infinite in this magical place, false starts and wasted effort don’t matter. Planning is for the old-school competition: we’re nimble disruptors! We respond to the market! Hustle overcomes all errors!
… Profit?
Companies who buy into this mindset get stuck in a Hustle Loop, where they’re too busy to make good decisions so they just try something because Hustle values activity over outcome. When that doesn’t work, they try something else, then something else, and so on, each effort more desperate than the last. When a leadership team is committed to hustling over thinking, this compounds across the organization as every department and person bceomes so frantic to prove their hustle that they start working at cross-purposes, pulling the company in so many directions that it loses all forward progress.
And then the money runs out.
Here’s the problem: hustle can’t cure dumb, and dumb hustling just accelerates a startup’s death spiral.
In reality, every startup brings extremely limited resources into a market already occupied by well-funded competitors. Even if you have an idea that no one has ever seen before — and therefore no competition — I guarantee that the moment you show any success you’ll see five copycats pop up carrying bags of VC money. Every moment is a precious resource in a startup.
Hustle can’t cure dumb, and dumb hustling just accelerates a startup’s death spiral.
A startup team is like an action hero with only a few bullets. If our hero “sprays and prays” when he faces off against the villains with their magically infinite ammo clips, he’ll be slaughtered. End of movie. Fin. He has to be smarter than his opponents, not louder.
(photo credit: Ilya Varlamov)
To survive, a startup must be efficient above all. Every decision must be treated as though the survival of the company depends upon it, because in some ways it does. Rather than asking, “am I hustling enough?” every team member should be asking, “Is this the best thing that I can be doing right now?” They have to make each shot count, because they might not get any more.
So what can we do?
First, don’t buy into the Hustle Myth and don’t peddle that poison to your team.
Stop saying, “We’ll win because we want it more than they do!” and start saying, “We’ll win because we understand our market better than anyone else and we know where the pressure points are.”
Stop glamorizing late nights and 24-hour Slack debates and start making room for rest and refreshment. Value outcomes over effort and quality over quantity.
If you’re a leader and you just love work and don’t know how to turn it off, it’s time for you to recognize that that’s your problem, not your team’s. Schedule those emails and Slack messages for tomorrow morning and give everyone else a break.
Value outcomes over effort and quality over quantity.
Next, stop hustling and start thinking.
What’s the highest and best use of your company’s time today? Every company has things that it must do, things it should do, and things it could do. Do you know the difference? If you look at the opportunities in front of you and only see “must dos,” then you aren’t thinking hard enough.
Where is your company going? It’s almost childishly easy to get lost when you’re only thinking about the next turn. You had an idea once for the company you wanted to build. Is that dream still alive, and is it the right one?
How do you respond when things go wrong? Even a brilliant plan can be overturned by changing circumstances, so do you keep trying harder or do you pause to reconsider your course? What metrics will you use to validate or invalidate a decision, and do you actually check them? The longer you’re on a false trail, the more precious resources you waste, so check your business map regularly.
Finally, we all need to recognize that we work better when work isn’t the only thing we do. We make better decisions when we’re refreshed and able to think clearly. When we stop living an adrenaline-soaked, lizard-brained, Hustle-bound existence, we’ll build better companies. And survive the process.
Being Silly for a Good Cause
Our friends at Name.com recently learned that Community Ministry of Southwest Denver, a community food and clothing bank, is about to lose its building and needs to find a new one. They leapt into action, launching a campaign to raise $800,000 through their #GiveABuck program. Their idea: a lot of people giving even a small amount can accomplish amazing things.
To raise awareness, company videographer Jared Ewy is creating a series of silly videos mimicking some of the top viral trends to tell people about the campaign and send them to the fundraising site CMSWD Rocks to make a donation. In his most recent effort, Jared invited a number of Denver tech community members, including our CEO, Jason, to join him in a carpool karaoke version of “I Will Survive.”
As Jason says, never let your pride get in the way of serving a good cause. And he didn’t.