Five Signs You’ve Become a Complacent Founder

We just hired our 30th employee. The days of co-working are long behind us. Our brick-walled SoHo office has consistent WiFi coverage; we’ve had a working product for the last 300+ demos. Finally, respected international brands are excitedly using our platform to scale experimentation and drive their agile transformations.

Life is -- comfortable -- for a minute. That’s not a bad thing by any means, so long as we don’t stagnate or become complacent.

“Success breeds complacency. Complacency breeds failure.”
Andy Grove, Founder of Intel

The growing company.

As a company grows, understandably it will shift from "figuring shit out" to executing. The company will transition from general roles where everyone wears multiple hats to an emphasis on specialization. There will be the embracing of a layer of management and delegation.

But reflecting back to the initial months, and think about what an average work day used to be. I don’t miss the endless grunt work, but I can appreciate the value in continuing to do some of that difficult work no matter what other priorities are in front of me.

That’s because I think it’s critical for founders to remain vigilant. The "that’s-below-my-pay-grade" attitude can set any founder and startup on a wayward path. Getting our hands dirty keeps us grounded, literally and figuratively.

To that end, I consider five activities in particular to be critical. Beware, if you stop doing any of them, it could be symptomatic of creeping complacency. Here are the warning signs (along with some more fluffy quotes):

#1 – You stop sending cold emails to broaden your network.

Don’t fall into the trap of thinking you know everyone there is to know, otherwise you’ll get blindsided by competition and miss out on big opportunities.

Some of the most important people to our business today are people with whom we connected within the last six months alone. And this is ongoing – I’m sure the next year will depend on people we’ve yet to meet.

At Alpha, we maintain a list of targets we want to connect with. The list includes possible customers, partners, journalists, authors, investors, advisors, and even potential future employees. I know this is crazy –but make sure to respond to cold emails.

In fact, I respond to every single non-newsletter email I receive, even if it’s with a simple ‘no thanks’. You’d be surprised, but sometimes cold emails can contain truly valuable information.

Don’t offload outbound cold emails to SDRs, PR consultants, recruiters, and assistants. As a founder, you have the best shot of anyone at getting a reply, while the connection you make will be much stronger afterward.

“If your business comes from relationships, relationships should be your business.”
Doug Ales, Sales Leader at WESCO

#2 – You stop being a part of and learning from the community.

Don’t fall into the trap of thinking you know everything there is to know, because great companies aren’t built from ivory towers.

Of course it wouldn’t be productive to attend every Meetup, but one of the early signs I see for startups on the verge of plateauing is an insulated founding team. They’re 'hard at work' and don’t have time to "get out of the office" or "shake hands."

While it’s fine to be busy and focused, I question productivity levels late in the evening, when time is better spent meeting and learning from people face-to-face. It’s a tired cliché at this point, but the world is moving incredibly fast. You can’t even remotely keep up if you don’t leave the office. Beyond that, attending community events as a speaker is an opportunity to listen, give back, and build a stronger brand in your area.

"I see life almost like one long University education that I never had – everyday I’m learning something new."
Sir Richard Branson, Founder of Virgin Group

#3 – You stop trying new tools to solve problems.

Don’t fall into the trap of thinking your way of doing things is the best, because you’re probably wrong (and even if you’re right you won’t necessarily always be).

There’s a wide spectrum in between refreshing Product Hunt all day and saying no to demoing any new tool that hits the market. Falling behind and being hampered by legacy tools is one of the costliest problems for big organizations, and it takes a proactive mentality to avoid a similar fate.

To put it into context, think about how difficult it would be for your company to operate without Slack. Aren’t you happy you tried it?

Our company continuously evaluates adopting new technologies, with the explicit rule that we probably won’t make a switch to anything that hasn’t been properly vetted by the market. Every single employee at our company has access to a credit card and budget to try anything they deem defensible.

In the last few weeks alone, we’ve tested a new ad channel (EverThere), switched contact management systems (from Contactually to ProsperWorks), and switched swag manufacturers (from CustomInk to Printful).

No tool or process here is sacrosanct. This mindset has enabled us to be incredibly efficient in areas long abandoned by companies of our size. For example, we’ve hired almost every member of the team using free recruiting platforms like rather than a recruiter or agency. We’ve built stunning slide decks and collateral without a single designer on staff by instead maintaining a $30 monthly subscription to Iconfinder. And, as we documented in a previous post on Startup Grind, we spend just $50 to produce new episodes of our industry-leading podcast, This is Product Management. Those savings add up and free up resources to invest in other opportunities.

“The most dangerous poison is the feeling of achievement. The antidote is to every evening think what can be done better tomorrow.”
Ingvar Kamprad, Founder of IKEA

#4 – You stop testing things that you don't think will work.

Don’t fall into the trap of thinking that opportunities are always blatantly self-evident, because the opposite is true.

You got here by doing something non-obvious – by pursuing a direction others before you said wouldn’t work. Remember that as you consider ways to continue innovating. Successfully being experiment-driven means testing and committing to unpopular and implausible ideas. It’s not easy and you only look like a genius after it works out.

We often get asked how a relatively new startup like ours managed to build some of the industry’s most popular content channels and resources, including our Medium publication and aforementioned podcast. The truth is we’re not hitting home runs every at bat. For every popular channel we’ve launched, there’s a half dozen that no one has ever heard about because we struggled to gain traction. At the time, many of those actually sounded like much better ideas than anything that’s actually worked out.

“Failure is an option here. If things are not failing, you are not innovating enough.”
​Elon Musk, Founder of PayPal, Tesla Motors, and SpaceX (a company literally dedicated to exploding and just recently successfully launching rockets)

#5 – You stop doing things that don't quickly scale.

Don’t fall into the trap of thinking that every investment has to pay off immediately or you’ll never achieve exponential growth.

One of the most common phrases I hear from other founder is “that won’t scale.” Everyone seems to be looking for a growth hack or a big PR win. Well, guess what, The Wall Street Journal isn’t handing out front page real estate. In the meantime, don’t scoff at a channel that could help you grind out five qualified leads per month. You can’t get to 100 without first getting to five.

Anyone can pick low hanging fruit, so defaulting to it is typically a fruitless and soon-to-be commoditized endeavor (see: Uber clones). Generating truly differentiated value takes hard work and a ton of time. In pop culture, innovation of this sort is described as revolutionary and instantaneous. Some breakthroughs may indeed be, but most begin as modest evolutions that add up to something impressive over time.

Don’t disregard playing the long game where a lot of grunt work up front is required for the chance of an eventual payoff. If scaling is easy or quick, then you’re probably not doing something of value. Only ‘thinking big’ is a recipe for complacence and failure. Start small, like you did when forming the company, and work iteratively toward a vision.

“It's not enough just to do something extraordinary initially. You have to make an extraordinary effort initially. Any strategy that omits the effort—whether it's expecting a big launch to get you users, or a big partner—is ipso facto suspect.”
Paul Graham, Cofounder of Y Combinator

It’s difficult as a founder to take a step back and ensure that you haven’t become complacent (it’s often unnoticeable from a first person perspective).

My list is by no means all-encompassing, and I encourage other founders to identify activities they personally deem indicative of ongoing vigilance.

After that, dedicate time to periodically reflect on your priorities and mindset. You may not always like what you learn but how you respond will make all the difference.

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