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You can’t go further…

“I’ve been in business for about a year and I’ve done well in revenue, but I’m killing myself to get to this point. If I go another year doing this, I can’t consider myself successful. It’s just not healthy.”

This is a story as old as time and one I hear all the time. When thinking of startups, we usually picture the VC-backed, tech juggernauts stampeding across the world fueled by vision and force of will. Yet, there’s a massive number of startups that are clawing their way to measurable success. Every day brings new challenges.

If I had to take a poll, I’d wager that there are many more in the latter category than the former. Entrepreneurs with a vision who are trying to build a company and grinding every day with limited resources. Dedicated dreamers who look around and sigh while staring at their next obstacle to get over. It’s a much more common scenario than most of the media or the business writers likes to let on. We know that anything less than trying to become Google or Twitter or Uber isn’t sexy! Having a sustainable, revenue-positive business that keeping tight control over unit economics doesn’t make for good stories. But, it is what drives the economy. …


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Several years ago, I was interviewing for an assistant professor position at the college I had been teaching at as an adjunct. Part of the process involved sitting with the provost and having a face-to-face interview. During this portion, he asked me what I would change about the current program. My response, which likely cost me the position, was simply that we needed to provide more classes before we gave our stamp of approval on graduates. As I saw him recoil in horror at the thought, I realized that was the wrong answer.

Since that time, I’ve had a lot of opportunity to think about this concept. First as that same adjunct teaching undergrads as well as eventually moving on back into the private sector leading teams of techs and engineers in various consulting roles and in C-level positions at startups. The one thing I’ve found almost universally is that no one truly does this critical function well. …


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Choosing to go down the path of founding a startup is often a pretty lonely and frustrating experience. It’s not all upward momentum and explosive growth. Sometimes it’s a tidal wave of disappointment and feelings of utter failure. It’s not uncommon for the well of optimism to run dry.

It’s in those darkest times that test who we really are. That is where experience is built and makes the wins that much sweeter. But, finding that strength to get up, wash our face, and point ourselves toward the world with enthusiasm can feel next to impossible.

This is compounded by the circumstances we find ourselves in at any given moment. Sadly, the world does not stop while we build our business. We are not only faced with the pressure of performing at our peak by our partners, investors, employees, and customers but also by those around us in our lives. …


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Everyone, deep in their heart, wants to see their startup become wildly successful; however, it’s amazing how many founders doom them to failure. Having worked with a lot of startups and companies at various stages including doing a fair number of postmortems, there are a few lessons to be learned.

So, let’s do our countdown of the three best ways to kill your startup…

Number Three: Pursuing Perfection over “Working”

We all want our dreams to be realized in a perfect embodiment of quality and execution. No one dreams of releasing a new product into the world held together by duct tape and bailing wire. No one longs to see their entrepreneurial baby come out only to need a lot of support and quick fixes to keep things running well enough to service demand. …


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As I write this, I’m sitting here in a hotel in New York City wrapping up a whirlwind tour of fundraising. Let me first say that I am tired. The kind of tired where you feel as though your entire energy has been siphoned away during the course of your activities. But, it’s been productive.

If you have a startup, you most likely are used to the fundraising exercise. You want to get a certain amount of cash from someone willing to give it to you. This is really a similar exercise, but like it’s been enhanced by some wonder drug or a kale smoothie or something. …


“We love your company and what you’re doing, but you’re still a bit early stage for us.”

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“This is great. Keep in touch because we really want to get in for your ‘A’ round.”

“We’re usually used to writing much larger checks. Let’s regroup in a while and see how things are progressing so we can jump into a later round.”

“We definitely want to come in on this round, but we need to wait for a strong lead to put it together.”

Welcome to the world of the private equity (PE), “It’s not you, it’s me,” brush off. If you’re new to the fundraising side of the startup game, you will hear these and variations on this theme a lot. Get used to it, especially if you are planning for PE-backed growth over multiple rounds. You are going to deal with a lot of rejection and take a lot of meetings where the only tangible result is a full bladder from the coffee you drank while giving your pitch. …


You’re sitting at a blackjack table. You have a 17 in your hand and your dealer has 18, what do you do? The fact is, if you do nothing, you’ve lost. If you take another card, you have a chance of losing or a chance of winning. The actual probability will be determined by the other cards on the table and what’s next in the shoe.

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This is risk. You’re in a tough spot and really have to take that next card. In a few seconds, the truth will be facing you, but that moment of decision is yours. Is your stomach tightening at the thought of what may come? Are you getting clammy hands at the prospect of winning the hand? …


I am a startup junkie. There, I said it. And what a weight off my shoulders finally admitting it.

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When I left college way back when, about the time I realized I actually didn’t want to be a history teacher in the public schools, I did what most wayward GenX-ers with no degree and no prospects did — I fell into a series of jobs in the bowels of corporate America. I served a tour of duty flipping burgers in a Wendy’s and I worked a bunch of positions at a grocery store. Neither of those roles held my attention or satiated my desire for more career satisfaction. But, these were very acceptable paths in my mother’s eyes for finding a starting place in life. …

About

Brad Bartram

I am a technical strategist and thinker who enjoys writing on the finer aspects of technology, business, compliance, and finance.

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