Two of the Dumbest Business Mistakes I’ve Ever Made

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//Read about more mistakes in the newest Startup Edition

“Do not fear mistakes. There are none.”
-Miles Davis.

We all make mistakes.

I’ve made a few mistakes in my time. I’m not talking about the garden-variety mistakes you might make in the course of the day. I’m talking about product development whoppers, or the kind you look back on several years later and wonder, “What was I thinking!?”

You make the best decision you can based on the information you know at the time and your framework for making decisions. There are a few decisions I wish I could take back, because if I could change them now, they would be great companies (or at least, I could feel like I made the right decision 10 years later). They were ideas for products that I still want now, that still solve a concrete problem, and that people are still willing to pay money to solve. (These ideas also work because they enable the businesses that use them to make more money and get more yield out of their current investment.)

What was my biggest mistake?

My Biggest Mistake was not trusting myself to make the right decision with the information I knew at the time. I didn’t have all of the answers – how to execute, how to find the money, how to deal with the ups and downs of being an entrepreneur – and I let that feeling of being out of my comfort zone make my decision for me. The lesson for next time? Be comfortable with being uncomfortable. Trust my gut more, and be in the moment when struck by a big idea that wants to be real.

Now, you decide whether I should have gone forward.

Here are the ideas that I had and decided not to do. Read them with the knowledge that you have in 2013, and decide whether you would pursue them today: I would.

Big Idea: Make the Grocery Store Easier.

Idea #1: Imagine if the next time you went into your local grocery store, there was a way for your phone to tell you the location of every product in the store, to remember your past preferences for shopping, and even to direct you in an optimal aisle-by-aisle route to minimize the time in store? And what if you received loyalty rewards and marketing offers that pertained to you? And what if you could check out of the store simply by scanning each item with your phone as you placed into the cart. That idea sounds promising and real in 2013, and quite similar to the idea my friends are pursuing at qThru.

When I thought of a very similar idea in 1999, even though the hardware and software was off the shelf and readily available, I didn’t go and build it. I made the decision that “I wasn’t the type to do that,” and “I’m not an idea guy” and let self-doubt make my decision for me. I can’t have that decision back, and I know that what I was really feeling in the moment was, “oh crap. I have no idea how to even begin thinking about that much less how to build and monetize it.” And, it happened again.

Big Idea #2: Make Waiting at a Restaurant Better.

Idea #2: Imagine you arrive at a popular restaurant. Because they are very busy, they ask you for your phone number so that they can text message you when your table is available. At the same time, they ask you to join their loyalty program so that you can participate in drink specials, learn about special events, and play games or trivia while you are waiting in line. It exists today – it’s called TurnStar – and I’ve used it. It’s pretty slick.

Why didn’t I build my version? It was called TextMyTable, and I was ready to go with the vision, the business plan, and the execution play. It was September 2008. Then all of a sudden the economy did a flip-flop and all of our assumptions about what was a normal business turned on their head. Or did they? I was stuck because I didn’t know how to raise the money to start the business or to grow the business in such a way that it generated operating capital.

What’s the Commonality?

In both of these ideas (and in others it’s not important to share here), I had an idea for a product or a service that was innovative. The ideas capitalized on a consumer need, solved an actual problem and had a reasonable chance at being successful. We could argue about the size of the market and the relative degree of success, and the fact remains that they were good ideas. And I made a mistake in not pursuing them.

What did I learn and what would I do next time?

The first thing I learned is that you can’t find out whether you’ll succeed with an idea until you try it. (Duh.) The ideas I think that would have been successful might have been abject failures, wild successes, or more likely somewhere in between. And I don’t know because I didn’t try them.

The second thing I learned from these mistakes is that collaboration is everything. I needed to do more to ask people to tear apart the idea instead of trying to build the whole business from start to finish inside my head. Groups like Startup Edition are a great place to get feedback, learn from other perspectives, and to reframe your questions.

And finally, I learned from my mistakes that it’s impossible to know what you don’t know until you do it. (Sounds like a Zen koan, doesn’t it.) What can you do about that? Admit that you’re going to make mistakes. Try to make different ones the next time you approach a problem, and learn from the results. Trust your gut.

The circle of startup life

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It’s a sad day in a way – today marks the end of Gist, a company I had the pleasure of working for through its evolution from a scrappy startup pioneering new ways to manage social contacts through its acquisition by Research in Motion – the BlackBerry folks. And it’s a happy (albeit bittersweet) day as well. The end of Gist is a great time to reflect on the nature and purpose of startups – how fickle they are, how fragile, and how magical.

I love startups because they strip away the unnecessary parts of corporate america and focus on putting together a team to address a market and (hopefully) to solve a problem that people (and customers) want solved. Asking customers to hire your startup for the job they want solved – and hearing feedback from them that you solved that job well – is a great rush.

The purpose of a startup is – I think – very simple. The goal is to either build a grand, successful business, attract acquisition potential (and culminate in an acquisition), or to fail – as quickly as possible. That sounds a bit harsh when you put it that way but consider it as an efficient use of capital to make more capital. Along the way there are great relationships built, features created, and features (and products thrown away or pivoted because … sometimes … customers don’t think the way that you do.)

Working in a startup can be quite tiring (even if it’s also amazing.) It’s hard because the impetus to get things done is almost certainly self-driven. Customers will ask you to build features and functionality, and the team is the only driver to actually make that happen. There are always constraints, be they money, time, or people. And the reward for working in that startup is most often the reward of a challenge met, a job (sometimes well) done, and the knowledge that “hey, we did that.” is quite cool.

And surviving and thriving in a startup (or in a small, entreprenuerial business unit after that startup has been successfully acquired) is an ongoing process. There are some days when it’s hard to listen to customers ask you about a feature that’s not done yet; or when you’re not sure what to do next; or when you’d just like more sleep. And there are more days when you look at what’s possible to get done in a brief amount of time with small amounts of resources and the result is nothing short of amazing.

Understanding the Startup of You

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Are you still doing the things you thought were going to be hard when you envisioned your role? Can you imagine someone else doing that job and explaining how it works to them? Are you learning new things and meeting new people?

Because you really need to be working yourself out of your current job (not in a bad way – don’t take the implication that you should sit around all day not doing things that people ask you to do while eating bonbons – but rather in a creatively destructive way, like what happens in a forest after a cleansing fire clears the undergrowth.) The current responsibility that you do is becoming more familiar every day, and unless you relentlessly chase newness (both in terms of the information you take in and in the way that you do it) you run the risk of becoming stuck.

What are some ways of creating your next opportunity within your current role (or adjacent to it?) Reid Hoffman and Ben Casnocha have some great ideas in their book The Startup of You that might point you in some interesting directions.Reed and Ben advocate expanding your current interests and making an aggressive effort to meet new people; trying new things that have potentially high value and low(er) risk; and understanding your true risk tolerance so that you can decide whether to make a new role out of a current one or create a new one overall.

One of the best ways to reinvigorate your existing role and to “level up” for the next phase of this opportunity is to challenge yourself by making a practice of meeting successful people. You might choose to seek out people in your own field; find someone in a different field entirely, or to build new bridges to new fields by meeting new people. Begin by offering, “how can I help?” and really listen to the answer. You may find that you can help the other person directly, or that you may know of someone else in your network who may be able to help them.

This is also a great opportunity to run a personal a/b test of your unique abilities. You have something to offer – your thoughts, experiences, and perspective, and meeting someone new is also a great way to practice your pitch and to see whether the ideas you think you’re sharing are the one’s you actually are sharing. Then, ask a single question of your new acquaintance: “what’s one thing that I could be doing to improve this idea?” and really listen to the answer. Keep doing this at least a few times a month and you will improve your ability to communicate (and learn important insights about your pitch or idea at the same time.)

Say Thank You – It’s the Best Advice I’ve Received

Thank you for reading this post – really!

When I started at Gist I had been on the job for only a few weeks when I answered a question from Brad Feld, one of our key investors. It must have been late at night and I was a little curt in my reply, and Brad shared a piece of advice with me that has improved every email and customer contact I’ve had since that evening.

Whenever you write an email, Brad wrote, “start by thanking the person who sent it.”

I was mortified. Not only had I screwed up by replying without thinking, but I had also said the wrong thing to a really important customer. As it turns out, this piece of advice was the single most important takeaway that I had from my 18 months at Gist and helped me to be much more successful in building a strong Customer Experience for anyone who encountered me or the company’s brand online.

There are 3 key points about thanking a person who sends you a question (even and especially if they are mad) that I’ve gleaned from Brad’s advice – I’m sharing them here to prevent other people from making the same mistake I did (you can feel free to make a different one):

  1. Thank the Person for Writing. As Brad pointed out, the first thing anyone wants to know when they send in a question is that you read their email. And thanking them can go a long way towards building a positive relationship with this person. Even if you need to give them news they don’t want to hear.
  2. Restate the problem to demonstrate to the customer that you did more than just thank them. In writing out your paraphrase of the problem, you can either help to lower the emotional charge of the situation and/or start to think about how to solve it (even if you don’t know how you’re going to do it just yet.
  3. And finally, let the customer know what’s next. If you know what’s going to happen, state it; and if you don’t know, make a plan that will give the customer some idea of when she will hear from you next.

I think about Brad’s advice often (thanks, Brad), and it’s helped me to be more responsive with all kinds of customers, and especially those who email me.

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Have you found the career trail?

Which Trail Do You Want To Take?

If you’re looking for direction on the next stop in your career, try going to a wilderness area or national forest for some tips (really!) Wandering around in nature will give you good perspective on finding your trail, staying on it, and being tolerant of ambiguity.

Your career “trail” makes much more sense when you look back at it than when you look ahead, as certain decisions just don’t have enough information available to be more than a guess – I think I want to go that way – rather than a guarantee – I know what I’ll get when I go there.

And you’re going to make some incorrect decisions: that is a guarantee. (Probably also some good ones, too.)

Finding Your Career Trail

It’s easy to find your trail – don’t you see the marker that says “TRAIL”? – and less easy to know at this point in time whether that one’s good for you. Choosing a well-trodden path guarantees that you won’t get stinging nettles or poison ivy or a cactus thorn by staying in the middle, and it also virtually guarantees that you won’t find any hidden surprises. It also ensures you’ll get back to where you started, and that you can tell people where you’ve been.

Did You Follow the Map? (Staying on the Trail, and if you should.)

Staying on the trail is a lot easier if people have been on it before and have left markers (they’ll usually remove or flag the obvious hazards. If it’s an unmarked trail, however, there’s lots of opportunity to go somewhere new without being reprimanded (but make sure not to find the rattlesnakes.)

What’s Next?

How comfortable with knowing exactly where you are on the career trail? Understanding the difference between what one person calls a “trail” and another person calls wandering through the wilderness can sometimes be unsettling (and hard to figure out which one you’re following.) If you do a better job preparing yourself for the type of trail you’re on, you’ll be more comfortable even if the going gets rocky. If you’re in Arizona, you should bring plenty of water, adequate provisions, a map, sunglasses, and sunscreen. On your career trail, you’ll need friendly guides, sturdy shoes, and a sense of adventure.

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