10 Years In Tech

Musings after a decade spent building SaaS startups

3 min read

Exactly 10 years ago today—May 10, 2010—I slinked through office doors that opened to my first day of work at a “real job.” I was plenty nervous as I entered a shared office space with dingy gray carpets tucked away in Boston’s Fort Point Channel. My whole career, quite literally, lay in front of me.

Today I can look back across a full decade that’s been spent building SaaS start-ups. In retrospect, I’m quite surprised how much I’ve come to enjoy and appreciate the career path I’ve chosen. The world of technology start-ups has been good to me—it’s provided for my family, it’s given me a wonderful amount of freedom to live my best life outside of work, and it’s been intellectually engaging and challenging throughout. I feel very lucky to be able to write that sentence.

As I’m now 10 years in, I feel like I can *officially* say that I have significant “experience”—I’ve definitely packed a wide range of experiences into the past decade. It’s a common sentiment that one year of start-up experience is equivalent to two years of experience at a larger company, which I wholeheartedly agree with. My past 10 years have included:

  • Bootstrapping a company to $7M+ in revenue
  • Starting a consulting practice 
  • Deploying millions of dollars of venture capital
  • Making the INC 5000 list of America’s fastest growing private ventures 5 times 
  • Leading marketing teams at four venture back companies 
  • Being fired 
  • Founding my own start-up
  • Presenting to Sequoia
  • Hiring dozens of marketers, designers, and writers 
  • Acquiring a company 
  • Getting acquired, twice 
  • Failing at a turnaround
  • Actually getting paid out on equity
  • Getting laid off

There are plenty of technology veterans who have been around the block far more times than I have, but I think these experiences, taken collectively, put me in a position where I can speak with credibility about the world of technology start-ups. Beyond that, I’ve always felt like a bit of an outsider in tech—I didn’t grow up wanting to be a tech entrepreneur and I don’t have the latest iPhone or a Tesla in the driveway. I’m not predisposed to looking at the tech world through rose colored glasses.

What I’m hoping this post provides is an objective look at the world of technology start-ups—the good, the bad, and the ugly. I hope for outsiders this provides a glimpse of what it’s really like to work “in Silicon Valley”—but perhaps more importantly, I hope it gives those that work in this industry the opportunity to step back and take an honest, macro-level view of a world that’s very easy to get lost in. This post is more filled with observations than lessons.

The Good Stuff

Tech is filled with really smart people

I am still surprised on an almost daily basis how many smart people work in tech. One of the most rewarding aspects of the past 10 years for me, without a doubt, has been getting to know and learn from so many intelligent people. As a US citizen, it’s very clear to me that many of our best and brightest go into this field.

Best of all, the types of smart people that you run into in tech run the gamut from highly technical software engineers, to massively creative designers and marketers, to analytical data wizzes and finance experts. It’s very difficult to work for a successful tech company without being exposed to hugely impressive colleagues with skill sets very different from your own. I find that refreshing. 

Beyond just being smart, I’ve routinely come across people in tech that are tenacious, objective, and have high emotional intelligence—so much so that I often find myself thinking, “It’s too bad so many of these smart people are building email marketing software!”

I can name dozens of people in tech that I genuinely find to be more impressive, smart, and thoughtful than our very best politicians, for example. If only we could get one of them into our elected offices.

There’s a wonderful creative, artisan aspect to building software

The world of technology start-ups—and particularly early stage start-ups—is a great place for artistic and creative people to call home. I wasn’t expecting this, but this observation snuck up on me as my own skills as a marketer matured and as I worked alongside colleagues that were designing and building software.

Before I lived it, I thought of the tech world as being very business oriented—a place owned by analytical types and developers writing rigid blocks of code that looked like gibberish to me. But there’s a very real reason why so many software entrepreneurs now refer to themselves as “makers” or “creators”—even in a role as technically oriented as software engineering, there’s a remarkable amount of artisanship and thought that goes into bringing something new into existence. This bleeds even more heavily into the worlds of marketing and UX design, where the very best teams are often differentiated largely by creativity.

Many people choose work in this field simply because they can’t help but use their skills to bring new digital products into existence, which is a practice and sentiment I can only appreciate. Perhaps best of all, the advent of cloud computing has made the barrier to entry in this field lower than ever before. Creative people with the thirst for working together have the opportunity to come together, create a bit of magic, and take control of their own destiny through their creative endeavors. 

Remote work is the best perk going—but it’s not “the future of work” for everyone

Many people who work in tech live so far in the depths of their own tech oriented bubble that they seem to lose all perspective on what’s going on with the rest of the world—that’s very much the impetus for this post. But nowhere is this more apparent than when it comes to the topic of remote work, which is being trumpeted from all directions as “The Future of Work!” The Coronavirus pandemic certainly poured gasoline on already smoldering embers.

Well, if you run a restaurant, or a hotel, or are a fireman, or work in healthcare I can assure you that the future of work is not remote. While more professions can work remotely than ever before, it still takes a fairly restrictive set of circumstances for remote work to even be possible. Tech is a field that does very much lend itself towards remote work, and that’s something that we can and should celebrate. The freedoms that remote work has afforded me is perhaps the single greatest benefit of working in this field.

People in the tech world who run around talking about remote being the “future of work” for tech employees are flat out late to the game at this point. Remote work is a setup that’s better aligned with deep work and productivity, and also dramatically opens up the talent pool that companies can hire from. While I understand the benefits of a co-located team, I fully believe that you’re knowingly putting yourself at a competitive disadvantage by not offering remote opportunities. 

The business benefits aside, the real benefit of remote work is it’s simply a better lifestyle for most workers. Nobody will miss their commutes and I promise productivity won’t plummet because your team members throw a load of laundry in the washer on their lunch break. 

I’ve been working remotely since 2013, when I walked into the office of the best boss I’ve ever had and asked for permission to work remotely. I was hell-bent on moving to San Diego, and had every intention of leaving a job that I loved if the answer was “no.” I was given the freedom to do so and I can say with 100% certainty that I’ve never worked so hard as a result—even when I could see the Pacific Ocean, sunshine, and my surfboard peaking over my laptop screen. Trust and true consideration for people as people is what drives performance.

The Bad Stuff

Tech has a real problem with hero worship

I’ve long been fascinated by the tech industry’s obsession with a small number of well known, serial entrepreneurs. You know, the Jason Lemkins, David Cancels, and Naval Ravikant’s of the world. This is not commentary on any of them—I mention their names just to bring color to the types of people I’m talking about.

When you become successful it’s only natural that people want to know how you did it, and I totally understand and appreciate how entrepreneurs can have fans. But in tech there is a small number of people that are quite simply worshipped as heroes by thousands of people who have never met them and really have little more than a surface level understanding of their accomplishments. Sure, this is pervasive in our culture at large—especially American culture—but tech has a serious problem with hero worship way beyond what I’ve seen in other industries.

I think this bothers me because I’ve been fortunate to meet many of the people that get put up on the hero pedestal—some of them are absolutely fabulous, but many of them are not. Some of these “heroes” put on a nice public facade, but behind closed doors are downright entitled and unethical—especially when presented with an opportunity to make a buck. 

I wish everyone in tech would think more for themselves and find the unsung heroes among us of which there are plenty—the majority of the best people I’ve come across in tech live happily in silent obscurity.

The tech industry is hugely financially motivated—but all too often puts on a guise of being “mission driven”

People within the technology world, from venture capitalists to founders like myself, are goddamn magicians when it comes to convincing others that they’re not in it for the money. Every venture fund and start-up founder has some lofty ambition to change the world for the better... a vision of the future that they’re working to make a reality... a dream that… 95% of the industry would immediately abandon if you cut them a sizable check.

“Every venture fund and start-up founder has some lofty ambition to change the world for the better... a vision of the future that they’re working to make a reality... a dream that… 95% of the industry would immediately abandon if you cut them a sizable check.”    

When I share this sentiment, people in tech squirm—they resist and push back on this truth. That’s really what’s maddening to me; why can’t you just admit that you’re in this for the (preferably fast) money? We live in a capitalistic society. Much of the reason we work is to make money. So why are so many people in tech hellbent on denying their true motivations?

I’d go so far as to say the tech industry has plenty of parallels to Wall Street—all the way down to a ridiculous amount of “insider trading” that goes almost completely unregulated. It’s happening in private companies as investors and executives share the latest tech gossip in hushed tones, and plenty of people are getting rich off of it. I know this comment will draw the ire of many—I certainly don’t look at the tech industry with the same level of contempt that I do Wall Street. But at least people in the financial world seem to be more transparent and forthcoming with their motivations.

The Silicon Valley formula, distilled, goes as follows:

  1. Get enough initial traction to raise funding. 
  2. Invest millions of dollars into growth while running your business at a loss. 
  3. Hopefully jack up your growth rate enough to be acquired for a massive sum of money.

I can assure you that most people in the tech industry spend countless hours thinking about how to make this happen, investing only a fractional percentage of time thinking about their impact. It’s worth noting that this phenomenon is likely strongly correlated with who the true owners of the business (the financiers) are—the more capital that’s pumped into a company, the stronger the financial motivations become. And in turn, the likelihood of the “mission” getting swept under the rug increases. 

I don’t want to discount that “tech” is quite broad and there are plenty of companies out there working on improving the human condition. Similarly, I don’t want to discount the importance of any job. Even the founder of a marketing technology start-up can take solace in the fact that their product does help other companies and people make a living and provide for their families. There’s absolutely value and honor in doing so.

But let’s not overstate the importance of our work behind some guise so that we don’t have to admit that the tech industry is heavily money motivated. Your email marketing software is important, but we’re not neurosurgeons here. Most people in tech would gladly give up their “mission” for an appropriately sized check—most surgeons would not. 

The tech industry is in a giant hurry

With the emphasis on outsized financial outcomes and the stories of the overnight tech successes that get popularized in the media, the entire tech industry often feels like it’s in a giant hurry. New waves of technology come and go in the blink of an eye, each with its own wave of new founders trying to flip their start-up in a newly hot market segment.

The ultimate irony here is that while this hurry can breed innovation, more often than not it’s actually hurtful to entrepreneurs and their chances of becoming successful. Start-up founders spend their time chasing after investors who are unlikely to see any return on their investments for 5-10 years, all the while deferring making any investments in their own business that don’t show short term ROI. The lack of self awareness is real. 

Worse yet, this hustle culture often results in people getting treated like shit. Founders hire executives looking for them to drive their overnight success, then move on before the person ever had a fleeting chance of meeting their goals. And when faced with an economic downturn, tech companies shudder their doors and layoff workers in alarming numbers because few industries operate with so little regard for profitability. The human level costs of this approach are really pretty ugly—all in the name of making a fast buck.

The more time I’ve spent in tech, the more I’ve come to the realization that a long term mindset is perhaps the greatest competitive advantage a company can have. When I look at the companies that are truly generating outsized returns—the exceptions being the Snapchat’s of the world—the common thread more often than not is a seasoned entrepreneur who invested and executed well in all aspects of their business across the better part of a decade. But you’d be hard pressed to feel that in the vast majority of tech companies. 

Other Observations

Not all “exits” are created equal

One of the most curious and least talked about sentiments in tech is this one—not all “exits” are created equal. The exit—loosely defined as successfully selling a majority ownership stake in your business—is the badge that we associate with successful tech entrepreneurs. We talk about exits in tech like we talk about Super Bowl trophies in football—you’re either an “exited founder” or you’re not and the minute you become one you immediately become tech royalty. 

“We talk about exits in tech like we talk about Super Bowl trophies in football—you’re either an “exited founder” or you’re not and the minute you become one you immediately become tech royalty. ”    

Once you enter this elite club, you no longer have to talk or associate with non-exited founders—they probably don’t know what they’re doing anyways. You’ve got a new clique now and your eyes on the next prize—the serial entrepreneur club! I’m poking fun, sure, but humor me. 

The truth of the matter is exits happen for a wide array or reasons.

  • For some entrepreneurs, exiting is essentially folding their hand—they haven’t been successful in growing their business and are ready to move on to a new project.
  • Other times, exits aren’t financially successful for anybody but a company’s product and employees end up in better hands at a larger company. The exit can be seen as a success from a people perspective, if not a financial perspective.
  • Investors often force an exit as a means of recouping some of their investment, even though the exit isn’t successful for any of the involved parties.
  • And yes, other times companies have built something hugely valuable and the exit is successful in creating a life changing financial windfall for founders, investors, and employees alike.

My personal favorite is when you see “serial” entrepreneurs with 3-4 exits on their resume, but they only have five years of work experience. While they may have *technically* sold something, this is pretty much a tell-tale sign that they didn’t create much of value.

If exits are our measure of successful entrepreneurs—which alone is problematic for many reasons—let’s dig a bit deeper. There’s an awful lot of nuance here and the devil is in the details.

Tech companies are horrible at deploying technology

Tech companies are horrible—HORRIBLE—at deploying technology. And to make matters worse, they again have just about no self awareness when it comes to this issue.

I’m not talking about implementing new software and tools—tech companies are fabulous at that, as they have the internal skill sets and know-how to implement new tools well. But techy people love technology and end up way over-serving themselves, resulting in a mountain of subscription charges, fractionally used tools, and others that simply drive little to no business value.

How many times have you received a Slack message from a co-worker sharing a new tool or piece of software accompanied by a note that says, “This looks pretty interesting. How can we use this?” This is completely ass-backwards! Software should be used as a tool that’s supportive of your strategy, not something that’s opportunistically driving your strategy. A contractor wouldn’t go out and buy a bunch of tools, then decide what to build—rather they’d design a project and then buy the tools that they need to complete the job. 

The world of tech start-ups accepts The Lean Start-up as gospel, but is conveniently out to lunch when it comes to their own use of software. I’ve yet to see a single SaaS company truly assess their use of each of their tools against the actual business value that the tool is creating. For as smart as people in tech are, this omission and lack of self awareness is strange at best. 

Don’t work in tech start-ups if you want to make money

It’s my strongly held belief that you shouldn’t work in tech start-ups if your objective is to make a lot of money. The idea that you’re going to start a company, work on it for 5 years, then exit for millions of dollars is largely a fallacy.

Let me also clarify that I mean this as it relates to early stage, technology start-ups. I am particularly tuned into this world—when I peruse Indie Hackers, attend MicroConf, or generally just talk to other early stage SaaS founders my experience is overwhelmingly, “Shit, here are a lot of really smart founders going broke or just barely eeking out a living.” There are many, many more start-up founders who irrevocably screw up their financial future than those that truly become rich.

It’s become en vogue recently for tech employees to share their incomes, which many folks have done to prove this point wrong. But these surveys are plagued by pornography bias—you don’t show it unless you got it. Beyond that, the common thread behind people earning outsized incomes in tech is that they tend to work at big, latter stage technology companies. You can work at Amazon, Google, Facebook, SAP, Oracle, or Intuit and make boatloads of cash. 

Companies like these often have plenty of mediocre people making lots of money—early stage start-ups are all too often filled with really superlative people going broke. If making money is your objective, choose your path wisely—or another industry altogether.  

SaaS companies need to have more collective accountability

With the aforementioned focus on making huge financial outcomes happen quickly, SaaS companies quickly become pressure cookers that both hire and fire fast. Best of breed SaaS companies are also hugely data driven, relying on metrics, KPIs, OKRs and other measures to manage their businesses—tech is way ahead of many other industries in this regard, which is largely a good thing.

But with the focus on short term outcomes, individual performance is assessed against specific metrics as a means of driving accountability—the VP of Marketing has a target number of leads, just as the VP of Sales has a quota, and the VP of Engineering is assessed against the number of new features they deliver. This makes logical sense, but in my opinion is enormously short sighted—the success of all these roles is inextricably linked in the context of a SaaS business. SaaS is way more of a team sport than most companies realize.

For example, if the product isn’t up to snuff or if the onboarding process is just a bit rough, even perfect execution by the sales and marketing teams will yield lackluster results. Likewise, a company that’s generating 2000 leads per month might be much better off focusing their sales team’s efforts on just 200 of the very best leads—but your VP of Marketing’s performance is being assessed against a lead quota. And ironically enough, it’s typically the developers—often the highest paid of tech employees—that have the least amount of accountability for delivering features that actually matter.

Especially in early stage tech start-ups, I think we need to see more collective accountability for company performance across functions. Your leadership team, collectively, should be on the hook for company performance far more than any individual should be assessed against a given metric. Building a tech company is a team sport and I don’t see most companies doing enough to instill a sense of team where people work collaboratively, and with accountability, to drive business performance. Nobody will lay down a sacrifice bunt—even when it’s needed—if their performance is tied to hitting home runs.

You begin your career focused on who you want to be, before you learn to focus on who you are

A career in tech follows a similar arch to our growth as individuals—what you’re looking for at the outset is most often quite different from what you come to value when you’re in the throws of the journey. This observation may not be specific to SaaS, but I think it’s exacerbated in our industry as a result of the hero worship and the overnight success stories that get glorified by the tech media.

When I started my career in tech I looked up at successful SaaS founders with envy, carefully plotting my course so that one day I could be like them. I needed a disruptive idea. I needed to be on conference stages sharing best practices. I’d need to learn to raise capital and recruit developers.

Over the past 10 years, those motivations have largely dropped by the wayside and my definition of “success” has changed. While I admire many entrepreneurs for their individual skills and talents, I’m no longer focused on how I can become them—instead I’m singularly focused on how I can be the version of myself that I admire most. I think this change will ultimately have bigger repercussions in terms of my future success and general satisfaction than trying to follow anyone else’s lead.

It’s worth noting that this sentiment can also be dangerous if it’s used as a crutch—it’s far too easy to say “That’s just not me,” anytime you’re asked to leave your comfort zone. How and when you choose to navigate that line is tightly correlated with success, however you define it. This is very much a work in progress for me, but learning to focus on who I am and how I can play to my strengths has been one of the most impactful areas of growth for me over my 10 years in tech.

This list is admittedly a bit random, but these items are all observations that stick out in the forefront of my mind as I reflect the tech industry at large. I hope this article helped bring some of the positive, negative, and less obvious aspects of a career in tech to life.

Enjoy this post? Follow me on Twitter for more. I tweet 10x per week about start-ups, SaaS, and building employee owned companies.

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