Entrepreneurs Answer: What’s the Best Startup Lesson You Learned?

What did I learn from that?

This question is a powerful follow-up to every major action you take building a new product or business. But it’s not often that we slow down enough to ask this of ourselves.

We recently asked a handful of entrepreneurs in the Verge community what was the most important lesson they learned in the last year. Luckily, they were able to slow their roll enough to share some thoughtful responses:

It’s a tough question to answer because it often requires humbling introspection. It means giving ourselves a good hard look in the mirror and taking ownership of where we are with our business. And we may not always like what we see.

The lessons are there, but they’re often shrouded by emotion and ego. So, here’s strategy for cutting through the head trash and getting to the good stuff:

1.) List your wins.

What did your business do that you are really proud of? It’s OK to brag here. This exercise is just for you. Make a list. (pro tip: caffeine, moderate alcohol, or even physical activity can be a productive catalyst here).

2.) List what’s wounded.

What did your business do that you are ashamed of or embarrassed by? Oh, c’mon… humble yourself here. You know your business screwed some things up this past year. Find your battle scars and business wounds, and make a nice long list. (pro tip: if you are prone to depression, maybe don’t drink alcohol while you do this). Get through it, and then move on to the next step . . .

Why Start a Business

3.) Ask yourself a simple question.

What was the main decision that led to this outcome? This question works for both wounds and wins. What you’re searching for here is the immediate action that led to the wound or win outcome.

Depending on how large your business is, this may not have been your direct action. Trace it back to the exact who and what of the action that produced your specific outcome.

4.) Keep asking that question.

Now that you’ve identified the direct action that produced your outcome, trace that momentum back a step further. What action or thought process was made by your business that produced your final outcome-producing action? When you find the answer, ask the question again:

What was the main decision that led to this outcome? Boil it down until you trace your steps back to your original entrepreneurial decision.

5.) Write down your answers.

You can map this thought process in a mind map. Or you can write it down as a short story, narrative, or whatever really brings this to life for you. But write the full sequence or strategy down for each big outcome. This ensures that you soak up and synthesize the knowledge that’s been lurking beneath the hustle and bustle of running your business.

When you get all of this out of your head and onto paper, it’s easier to remove the ego and emotion from your business wins and wounds. That’s an important step because emotion and ego have a tendency to distort your perception and prevent you from understanding the larger forces at play.

Once you have your winning strategies and wounding sequences identified, you can take action on your new insight. Develop new habits and business systems that based on these strategies and sequences. Like the entrepreneurs who shared their big wins and wounds from the past year, you can leverage your experiences to build a stronger business.

Make this next year the best one yet!

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About Matt Hunckler
Matt Hunckler
Matt's a founder and organizer at Verge. He's a connecter, writer, and habitual start-upper.
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  • Dante Cook

    Matt – I really appreciate you posting this video! This is the kind of stuff that the Indy startup scene needs to hear.

    Two comments that were made that really stood out to me were:

    The first comment was from Todd Saxton when he “You never de-risk yourself, you just move from uncertainty to more uncertainty”.
    Ok I’m probably paraphrasing there but that is a profound statement to me for two reasons:
    1) It implies that you are advancing from your current challenge to an unforeseen challenge.
    2) It highlights the importance of risk.

    Growth never happens in a comfortable state and it certainly never happens in the absence of risk. There’s always room to grow and there’s always opportunity for improvement. This comment is a great one to hold onto in the moment when you’re feeling afraid to take that leap forward. Loved it.

    The second comment I really loved was from Lawrence at GetSayDo. Dude’s stage presence is amazing and I’m always super excited to see minority representation in our tech community, something I think this community needs more of.

    His comment was “When they (potential client) asks you that million dollar question, what’s (Your company)?, do not answer with descriptors & features”

    I love this statement because coming from the B2B marketing world, this is so prevalent. Nobody cares about features and functions! They care about about how your product makes them feel. It’s the classic case of Apple vs Microsoft and why Microsoft’s new Ad campaign is absolutely horrible IMO. They’re talking about features.

    If you’ve ever met an Apple fan, there’s no feature that will get them to relinquish their loyalty to Apple because there are clearly superior features on Android phones and Microsoft tablets… That’s not the point.

    What about your product or service will make them fall in love. One of the best quotes I’ve read on this is from Bernadette Jiwa in her book difference when she says, “Marketing is not a department, it’s story of how we create difference for our customers.”

    Matt – thanks again for sharing this. This was awesome and it was a bright spot for me here on my morning break!


    • Appreciate your thoughtful response, Dante. I completely agree with the importance of risk. I also think it’s important to really FEEL that risk. Get real with what life will look like if you don’t pull it off. Then get inspired by the potential of how life will be when you DO pull it off. Hugely motivating.

      Awesome comment on minority representation. This has always been important to me, and I’d love to collaboration to expose more of the stories that go untold and encourage less represented groups to join the community and launch their businesses. I’ll shoot you an email!

      P.S. Love that quote. Checking out Jiwa’s book now…