This article, by Gumroad founder Sahil Lavingia, should be studied with an open mind by anyone aspiring to scale a startup.

I thought Gumroad would become a billion-dollar company, with hundreds of employees. It would IPO, and I would work on it until I died. Something like that.
Needless to say, that didn’t happen.

Now, it may look like I am in an enviable position, running a profitable, growing, low-maintenance software business serving adoring customers. But for years, I considered myself a failure. At my lowest point, I had to lay off 75 percent of my company, including many of my best friends. I had failed.

Fear is a powerful motivator, and for many of us, fear of not reaching your goals can be outright depressing. It’s so easy to get lost in the ambition of building something so outrageously successful that you overlook the pleasures of what you’ve already created.

While Sahil learned a lot about how to run a business (and how not to) through this journey, I believe his most impactful change was in his own perspective of himself.

I think we’re all guilty of putting too much pressure on ourselves to be something. And while ambition is necessary, decisions should be made with present reality clearly in focus.

Now is the only part of life that matters. Don’t lose sight of how to add the highest value today because you are sweating what the future may hold. It’s easy to lose everything that way.

Listen to my interview this morning on the B2B Growth Show, discussing my latest article The Art of No Deal.

It was a great time, and Logan is a great host. I’ve been a long time listener, and honored to make an appearance.

As salespeople, we train ourselves to pursue and close deals. To be the breadwinner — the rainmaker. We network, we make phone calls, and send emails, all so we can get someone to hear us pitch our product or service, so we can make a deal.

Without the “deal” — the agreement we make with our prospect to trade our product or service for money — our jobs are on the line. After all, there are quotas to hit and competitors to squash. Because of this, in many organizations, the sales team is the first to win, and the first to lose. When we are successful, the company is flush with cash, and everyone breathes a little easier. But when sales are low, all eyes turn on us for being ineffective.

All that puts a lot of pressure on us to deliver.

To make things worse, there’s not enough to go around. Competitors are always out to steal market share. Customers keep looking for better options. There are only so many companies in the marketplace to begin with. Sometimes it can feel like we’re fighting for table scraps.

With such a limited number of opportunities, it’s hard to get our customers to listen to us. Voicemails aren’t returned, and our emails discarded. Despite our best intentions, we’re making noise.

This makes us selfish. We grab whatever deals we can get, and we hold on to them with all our might. We fight to win and keep those customers. Yet, in the end, many prospects still walk away without spending much money.

As a result of these shortfalls, we hustle to make more calls, send more emails and create even more noise.

How’s that working out for you?

Value is immutable. Your prospect cannot ignore it. Even if they didn't ask for it or pay for it, it is still valuable. Value is valuable.

Consider for a moment that our selfish attitudes are the root of the problem. Prospects buy when they perceive value for themselves. We aren’t fooling anyone.

Don’t get me wrong, I’m sure you have a great product and the best of intentions. You’ve no doubt put a great amount of time and effort into your sales presentation. It’s full of metrics, case studies and all the things you learn from sales books. Your prospects hear pitches full of promises all the time. They won’t care what you have to offer unless you actually deliver real value in your conversations. The problem is that we are creating value conditionally. We’re trained to hold back the value our product or service has to offer until after the customer pays.

But value is immutable. Your prospect cannot ignore it. Even if they didn't ask for it or pay for it, it is still valuable. Value is valuable.

If you move your sales approach away from “here’s what you’re going to get if you buy from me” and instead lead by creating actual value, then you’ll cut right through all the noise. Your prospect will call you back, return your emails, and even thank you for reaching out.

For example, if you pitch your prospect the potential cost savings that your product has to offer, they will mull it over in the back of their mind until they forget about it. But, if you bring a line by line plan which demonstrates where the cost savings come from, your customer is more likely to act. After all, it's in their best interest to do so. In that case you delivered value through research, understanding and hard work, rather than talking in front of a pre-canned slideshow.

Don’t make the mistake of thinking that creating value unconditionally is the same as free work. Value is short lived if it’s not sustainable to produce. You cannot afford to deliver anything of value without the resources to do so. As sales people, its up to us to take the first step to demonstrate that value.

This change in attitude positions you as a partner with your prospect. Your successes and failures become aligned. Rather than selling a product or service in exchange for money, you’ve worked together with your prospect to find a sustainable way to create value forever.

Mutually sustainable value between two parties has no limits. When the deal is valuable to all parties, who interact as one, the benefits can compound infinitely over time.

“If you think about it, Airbnb is like a giant ship,” he says, holding up the napkin. “And as CEO I’m the captain of the ship. But I really have two jobs: The first job is, I have to worry about everything below the waterline; anything that can sink the ship.” He points to the scribbled line of waves that cuts the boat in half, and below that, two holes with water rushing in.

“Beyond that,” he continues, “I have to focus on two to three areas that I’m deeply passionate about—that aren’t below the waterline but that I focus on because I can add unique value, I’m truly passionate about them, and they can truly transform the company if they go well.” The three areas he’s picked: product, brand, and culture. “I’m pretty hands-on with those three,” he says. “And with the others I really try to empower leaders and get involved only when there are holes below the waterline.”

Leigh Gallagher

There’s been a lot written about the strategic focus of successful entrepreneurs. Eisenhower’s Matrix, Peter Drucker, and others.

I find Brian’s approach refreshing: follow your unique strengths, empower your team, and fix the problems that might sink you. His distinction of patching holes only below the water line is especially meaningful to me as I often pick the wrong problems to get personally invested in.

8 A7 E6346 4752 4871 96 D8 C1 B60 Bb121 C0

On a scale of 0-10, where 0 is “fired and escorted out of the building by security” and 10 is “left entirely of his own accord on wonderful terms,” my departure is around a 4. That makes today a hard one, cognitively and emotionally. I have a lot of sadness, a heap of regrets, and a smattering of resentment too. But I am, deeply, deeply thankful to all the people who supported me and Moz over the last two decades.

Rand Fishkin

Sad news that feels a little too close to home.

Maybe it’s because Rand and I started our companies around the same time. Maybe it’s because we fought the same roller coaster of growth. Maybe it’s because the idea of being ousted from the company I founded is too difficult to comprehend.

Rand and the company he built has been an inspiration to me for years. I wish him well and great success with SparkToro.

There are times when the world beneath you seems like a treadmill, and you just can't run fast enough to keep up. For every critical project you complete, three new ones show up. Your call-waiting dings twice during a brief call. The stack of "I need your input" memo's is deeper than you'll ever work through in reasonable time.

And while there are plenty of useful techniques for prioritizing, delegating, and staying effective, there are still moments where no system will work. It is, frankly, an impossible situation.

This has been my life for the last few months. My natural inclination is to raise my energy to keep up as best as I can. To push a bit harder, work longer, be more aggressive, and fight. As a result, my coach dubbed me the "crazy person" in the office. I have become so focused on my goals and aspirations, that I don't realize the side effects on the morale of my team and my family. I have become obsessed with keeping up with the promises on my desk, that I've dropped the ball on the implicit responsibilities that are part of having relationships with other people.

In a moment of clarity over the holidays, when the work came to a stop, I realized that it's best to use these moments to do SOMETHING great, rather than EVERYTHING poorly. I realize that decision comes at a cost of discouraging others, for they are also in the impossible situation and just looking for a little help themselves.

Want to get better at a sport? There are clearly documented methods and approaches to practice. Want to get better at playing guitar, the drums, or the sax? Same thing.

But with those, even if you practice poorly, a certain number of reps will get you somewhere. And the reps are easy — you can sit down and practice the drums for hours, if you have the time.

I have written quite a bit over the years about accelerated learning, and practice techniques for learning new skills. Like Jason, I too have found it very challenging to practice management skills.

Managerial trials and reps are much harder to come by. And when you practice being a manager, you’re already on stage. Your flubs have consequences. Fucking up could cost you or someone else their job. It could cost a business money, customers, reputation. But when you practice guitar you can sit in your basement, alone. No one cares, and there’s nothing at risk, if your pinky can’t stretch three frets quite yet.

I don’t know… There are a lot of reasons it’s so easy to be a bad manager.

Another reason is that you feel like you have to contribute when there’s really not a lot you should be doing most of the time. Many managers over-involve themselves. Not even micromanage, but are simply around the work being done too often. They get in the way. It’s an easy mistake to make when you’re trying to prove yourself. Especially early on when you’re job title doesn’t really line up with your experience. You’re still just practicing.

Jason Fried

Last week I attended the Fourth Global Forum for Business as an Agent of World Benefit. One of the key topics was the implementation of Appreciative Inquiry, which really challenged the way I think about how I understand the value systems of my coworkers.

At its heart, AI is about the search for the best in people, their organizations, and the strengths-filled, opportunity-rich world around them. AI is not so much a shift in the methods and models of organizational change, but AI is a fundamental shift in the overall perspective taken throughout the entire change process to ‘see’ the wholeness of the human system and to “inquire” into that system’s strengths, possibilities, and successes.

Appreciative Inquiry: Organization Development and the Strengths Revolution. In Practicing Organization Development: A guide to leading change and transformation, William Rothwell, Roland Sullivan, and Jacqueline Stavros

The passing of my grandmother Joyce last week kicked off one of the worst weeks of my life. Her death was instantaneous, but unexpected. She felt no struggle, fear or pain. She just left. For her, a happy moment with her husband turned into an endless emptiness here on earth.

But for me and the rest of my family, our lives went from our daily routine to a tragedy we could barely contain. It didn’t feel so much like driving your car into a wall — even that gives you a few seconds of preparation — but more like waking up in the hospital not knowing what happened to put you there. My family and I aren’t wrestling with what happened in that moment that she died, we’re trying to figure out what happens next.

After a few days of anxious preparations, we had a funeral, buried her, and people went back to their homes to get back into the routine of their home lives.

For me, this idea is highly discomforting. Life isn’t the same anymore, and pretending it is just stresses me out. So, I left town to do some soul searching.

What I’ve Learned Through Reflection

Bear with me a bit, as I’m still processing all of this. It all happened just a few days ago.

I have one realization that keeps coming to mind as I reflect: “routine” doesn’t mean “comfortable.”

My life doesn’t feel routine while I’m living in it minute by minute. While I’m at work there’s an endless stream of growing pains, client challenges, systems to improve, sales obstacles and the like. I’m not working on a monotonous assembly line. Every day is new and challenging. I guess I thought that a routine would set-in once things were well oiled and smooth running. At that point, I believed I could use that newfound freedom to shake things up to get us to the next level.

Having a week to step back and process things, I realize how routine things actually are. Week after week, I help keep things in the current mode. I support people to do better work, but only within the boundaries of what our work currently is. This is routine, and I am a part of the grind.

Routine is the seed that grows complacency, which creates mediocrity. Perhaps I’ve already fallen back to mediocrity, and I didn’t even recognize it. It’s time for me to force a change in myself.

What To Do Next?

Honestly, I’m not sure exactly sure what happens next. I’m still trying to sort that out. But, I know that I’m not the same person I was a week ago. I know I’m less tolerant of perpetuating my routine. As a natural result, I feel some changes coming on:

  • I need to empower my team even more than I have, by encouraging them to solve their own problems so I have more space to expand the business.
  • I need to be even more vigilant with how I use my time. I must learn to say no to things which seem important, if they hold back larger opportunities.
  • Continue to support the tremendous team we have, with even more vigilance than before. Importantly, I need to stop coddling them as much as I do.

The fact that I was able to walk away in an instant, for over a week, and the company continues to thrive is a testament to the amazing people on my team and the company we have created together.

Right now I’m grieving. But when I come back, I'm going to downshift and punch the accelerator.

I'm an organized person. Actually, that's probably a massive understatement. I've obsessed over personal productivity for 15 years, and created systems to organize my rather chaotic life. Living messy is hard for me, and I constantly need to remind myself that often times, its my job to mess things up.

Here's the thing about valuable people. They always have too much to do. It's a simple case of cause and effect. When you are valuable to others, they want and need more of you. This doesn't scale. The more people learn to depend on you, the less able you are to help them.

As CEO, there's nothing more valuable than your time. Your time is your ability to help. It's why we say "thanks for your time" when someone serves you. Time is everything.

And so, to be valuable to many people, in a finite amount of time, things fall apart. It's physics, there's just no getting around it. You can't fit it all in. And so, we create a huge mess.

  • We are late to meetings, and not in the totally excusable 5 min "sorry for the traffic" late. Seriously late.
  • We drop the ball on promises. Things that really matter to real people you care about.
  • We make silly mistakes by taking shortcuts. Personally, I'm guilty of delegating things to my team without good expectations.

You're probably thinking that I'm a crazy person. With some better GTD coaching, better delegating, and great supporting staff this would be much more controllable, right? Surely executing more effectively would give you more time back, right? Not so. I've been deluding myself with this argument most of my career.

Here's the truth. Better productivity systems, organization and staff are critical tools, but they make you more productive. That means you can serve more people with your time, but it only overload your plate even more. You become more like a stunt car driver than a civilian driver. Barreling at high speeds, fast turns, unknown obstacles, and an occasional crash. When you drive fast, no matter how experienced, you make a mess.

Intentional Mess Making

You don't always get the luxury of executing the projects in front of you. Rather, its your job to decide what initiatives need to happen. You are a strategist.

And so, you can really shake things up in your organization. You come up with a new idea and toss it to the team to catch. They aren't always ready. After all, you didn't have time to comprehensively prepare them for this project, did you?

As long as you pick these moments wisely, the team will grow stronger and the company more valuable with each mess they inherit.

So, what do we do?

There are a few things we can do:

  1. Never give up your pursuit of productivity. This is not a reason to stop trying to organize. Remember, these systems do make you more productive.
  2. Hire and work with a great assistant. Delegate the mess. Empower them to find the most important content for you.
  3. Most importantly, surrender to the mess. Don't let it stress you out. Stress will kill you, literally. We need you, so stay calm.