Top Lessons Learned as an Entrepreneur by Neil Senturia



“Let your hopes, not your hurts, shape your future.” — Robert H. Schuller

Editor’s note:  This is a guest post from Neil Senturia on his lessons learned as an entrepreneur.

Neil is the current CEO of Blackbird Ventures and the author of I’m There For You, Baby; The Entrepreneur’s Guide to the Galaxy.

As an entrepreneur with more than 25 years of diverse entrepreneurial experience, Neil has re-invented himself several times in his relentless pursuit of entrepreneurial success. 

Without further ado, here’s Neil …

Entrepreneurs Need to Get the First 10 Things Right

To be successful at your start-up, you need to get the first 10 things right. In other words, you need to bat .1000 on the first 10 decisions. After that, you can bat .400, and in the aggregate, you can still make a strong company and a lot of money.

So, when I teach this concept to students at UC San Diego and San Diego State, they always raise their hands and ask politely, “OK, so what are they?”

My answer infuriates them: “They are different every time. But you still need to bat .1000. The first 10 are the most important, they cannot be finessed or nuanced, they need to be dead on, rock solid, concrete and correct.”

Embrace Ambiguity

So here is one rule that is constant. The entrepreneur must not only tolerate ambiguity but in fact they should embrace it. The willingness to not know what you need to know informs the decision- making effort—for example, the effort to define the business model and the product.

You would think that product and business model are what you have before you start the company but in fact, what you have is a quarter-baked idea, based on some half-baked assumptions that rely on some raw opinions.

Step One is Taking the Effort to Find Out What You Don’t Know

The concept of ambiguity implies that you are not sure what the business really looks like. Only 20% of companies actually end up doing what they think they set out to do on day one– the day they finished writing the business plan or the infamous 13 slide power point with its attendant hockey stick and the verb “we will.”

“Will” is a powerful word. You think the venture capitalist wants you to make a presentation with answers, and what I now strongly believe is that presentation should mostly have questions.

I am not being cute.

What I am suggesting is that step one of the start-up is the effort to find out what you don’t know.

This is the embrace of ambiguity. This is the willingness to change your mind, your plan, and yes, your underwear.

Changing Your Mind and Your Plan is a Good Thing

Currently, I am the CEO of a start-up in the alternative energy space (, and I recently was speaking with one of our key investors. I told him that we were going to make DME instead of gasoline. The various twists and spins and reasons are not relevant.

What is interesting is that one of our key investors was happy with the switch. Another one said, “You have changed your plan. You told us one thing, and now you are telling us another.”

Now I viewed changing my mind and our plan as a good thing. It might save you guys $25 million while some of our investors thought that changing your mind indicated weakness, vacillation, uncertainty, confusion.

The entrepreneurial spirit demands that you be willing to tack and jibe and then tack back (I race sailboats) because things change, and you are always looking for the right wind on the right side of the course with the right pressure. If you fear reprisal when you change your mind or your course, then you will not get one of the first 10 things right and you will not bat .1000.

When You Make a Big Mistake, Fix It

Here is another example. Recently I built a new house, and the day before they were going to pour the footings for the house, I realized that I had made a mistake– a big one. I had miscalculated the dimensions. I had two choices– pour anyway since the concrete trucks were in front of the house or stop the presses and send everyone home and fix it.

I picked the second option. It cost me seven months and some serious money. But I have been living in this house for five years, and immodestly I would say it is quite lovely. The proportions are now correct.

Wade Through the Ambiguity

It is mandatory to seek the correct answer and to be willing to wade through the ambiguity of indecision and the fog of revenue calculations and the mist of customer adoption.

Because once the footings are poured, the damn thing is cast in concrete.

Ambiguity is your friend. Love it and embrace it.


  1. What’s up Neil,

    Ambiguity is definitely my best friend. I plan on shooting a video promo video for one of my stories. And I’ve never done this before. But my attitude is greatness. My attitude is something creating worth remembering in the hearts of millions. My mind is, lets step into the darkness and become the light. This is just the way I’m programmed to think. And as an Entrepreneur, it took me years to create this mentality. But like they say, it’s better late than never. So i don’t mind missing a few

    But congrats on being a CEO….what a title…i see myself as this as well. Peace brother. Nice too meet you!

  2. I like your take on ambiguity – from what I witness right now it is the enemy #1 of so many and the gold opportunity of so few…

  3. Neil!

    I love this: “They are different every time. But you still need to bat .1000. The first 10 are the most important, they cannot be finessed or nuanced, they need to be dead on, rock solid, concrete and correct.”

    When I read the preceding sentence, I had the same reaction as your students and your response made me laugh because I didn’t expect it…and it’s dead on. I’ve experienced this dance with ambiguity and it is something to find comfort in, rather than resist.

    In fact, I’d venture to say that some of your most genius decision arise out of allowing yourself to wrestle with ambiguity, and when those decisions are repeated they result in success.

    I’m all about changing the plan if need be. Sometimes people fall in love with their own idea too much. But if ain’t working…you have to fix it, even at your ego’s expense. Otherwise, you can kiss it (your idea and you biz) bye-bye!

  4. Interesting ideas and concepts shared – thank you – made me think.

    My partner is a very sustainable, green architect who has done amazing work for 30 years. He never gets the big jobs first or the big design jobs first either….He does lots of little jobs and he gets to show off his design skills….but the point is that on all the huge jobs the big guys almost always have to call him in at some point to fix the mistakes they made because they just studied LEED work and passed the exams – they have not experienced the work first hand – My partner is the whistle blower on a huge project for the state which because the engineers did not correct the mistake at the time has cost millions of dollars in repairs and law suits.

    I think arrogance and greed can interfere with what one is looking at and testing.

  5. Thanks Neil (and JD).

    How I wish there were more people talking about how it really is to start something. All that guff about being able to plan and implement. If it were that easy we’d all be millionaire entrepreneurs. If you think I find the standard advice annoying and frustrating, you are not wrong.

    Steve Blank writes a blog that emphasises that the start up is not a small big company but is looking for the right business model rather than implementing an existing one and such. Readers who resonate with this piece may find it interesting. It is currently about trying to teach a class in entrepreneurship.

  6. Hi Neil and JD,

    Very nice post! We all have to learn from our mistakes whether they are big or small. This is one of the major keys to success. Changing ones mind is crucial when it comes to life, especially in business. If we are not flexible, then this can harm us very much and will limit our growth. Thanks for sharing 🙂

  7. Neil, I must admit, your first admonition to “Embrace Ambiguity” caught me off guard. I hear so many business geniuses and TED-Talk gurus talk about how important it is to KNOW YOUR OUTCOME, and yet it makes perfect sense that you should never think you have your expectations figured out. Give yourself room to learn and be surprised. This was a mind-blowing concept for me. Thanks for bringing it out. It is clear I have probably hindered myself in thinking I had to have everything planned out and NEVER stray from the plan. I love it!

  8. Hi Neil,

    The thing I loved about this that it challenges what the status quo teaches. I love that. Because I don’t believe that there’s only one black and white answer, there are others. And this proved it.

    Embrace Ambiguity! It will exist, there’s no way around it. IT MAKES SENSE. It’s just so foreign that seeing it, before reading it raises our intellect flag – as it did for Bryan above (and myself initially).

    Thank you the treat Neil.

    Hello J.D.!

  9. Hi JD and Neil .. thanks for the post – really interesting and your story telling around ‘ambiguity’. It’s so important to be open-minded and ready for whatever comes … evaluating and then needing to change your mind makes life easier sometimes and in the long-term gives more flexibility.

    Like it .. I was told early on in my working – make a decision – if necessary it can always be added to, changed later on .. but doing nothing is not an option .. moving forward is the thing & learning from those lessons as we go – too true.

    Thanks – JD – you always bring us stimulating guests .. cheers Hilary

  10. Nice tips! I will take note of the one about correcting the BIG mistakes we make. Mistakes are often unavoidable, what matters is that we are able to correct them. It doesn’t mean we quit, but it means we have to learn something and then carry on!

  11. I love the sound, pragmatic wisdom here. There are no straight lines in the universe. Flexibility is an important quality if you intend to aim and hit the bullseye. When we take our ideas from our head into the real world ambiguity comes with. Anticipating that the School of Hard Knocks is waiting to teach us lesson will have us flexible and open to the best possible solution. So many are tricked by hardened thoughts that are unbending and demanding.

  12. Like your style Neil

    Your final line…

    “Because once the footings are poured, the damn thing is cast in concrete”

    is so true for many things including blogging.

    Make sure that you have the right domain name – the domain name represent the footings of your blog.
    Start with good foundations and the rest will follow.

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