Talk To Enough Successful People And Patterns Emerge

I am truly grateful for what have the opportunity to do each and every week.

We started Founders RAW a few months ago and are almost to our 10th full conversation with entrepreneurs here in Seattle.   For those who aren’t aware, Founders RAW is a new multimedia property where we showcase videos of casual conversations with other startup founders.  When I realized I was having great conversations with my founder friends at local startup events I decided we need to record this stuff and push it out to others.  Maybe you can learn something as well.

Check it out for yourself >  Founders RAW.

I typically sit down with one person each week, grab a beer and dive deep into what it’s like to start a company.  One of the big things I have taken away thus far is how patterns emerge during these conversations.

Founders RAW behind scenes

Sitting with Simon Crosby during our Founders RAW conversation at the WTIA TechNW event in Seattle.

What do I mean by patterns?

By patterns I mean in how these founders identify the challenges they face and how they dealt with and overcame them.  Not to say all entrepreneurs experience the same things, but as I peer deeper into my conversations and read between the lines, certain characteristics or principles seem to be emerging.

The founders also seem to allude to similar experiences of company near-death and despair – yet they continued forward when all seemed lost.  So yes, no one is immune to the inevitable challenges and tough times ahead.

Benind scenes 2

Sitting with Carlos Guestrin during our conversation at the WTIA TechNW event in Seattle.


Each founder I talk with embodies a strong sense of vision – they know where they are going and what they want to accomplish.  Vision is what sets them apart from their competition and allows them to navigate changing waters when their market matures and shifts with the times.  John Cook had a vision of digital media even when he was working  as a reporter for a traditional newspaper.  Amazingly, he pitched them on rolling out a whole new concept involving the web and digital properties, only to be shot down my management.  So he left and started it himself!

We know now who had the vision and who was stuck in the past.


The founders I have spent time with all have the quality of strength, meaning they are able to endure and deal with the challenges ever-present in entrepreneurship.   Whether it be dealing with co-founder issues, standing up to advisors and investors when their business model is challenged, or when push comes to shove they determine to out innovate the competition.  Adam Lieb, founder of gaming social network Duxter, displayed a strong sense of character as he detailed out his experience raising money from angel investors.  It’s not easy for startup founders to raise money, especially here in Seattle vs down in the Valley.   The lesson I took was investors want to invest in strong, vision oriented founders, not weak leaders who will bend at any sense of difficulty.


Lastly, as market forces change the tech landscape founders must be flexible and change with it.  Advancements in technology are only speeding up and drastically influencing how we build our companies.  Just a handful of years ago AWS/Amazon was nowhere to be seen.  Now, because startups can now host in the cloud using services like AWS and Heroku, startup costs have dropped dramatically and thus have allowed a founder to launch a company in under $5K initial investment.   Bob Crimmins made a huge point regarding this as he spoke about what he is seeing with the TechStars companies he mentors.  “They act quickly, test frequently and iterate often.”  That is why the successful ones are growing – the lowered cost to start and grow has allowed for more/quicker iterations of web products and services.

It’s been fun thus far and I can’t wait to see what happens next.  And I think you should do this too!  No, you don’t have to record your conversations like we are but I think Mark Suster was onto something when he says you should take 50 coffee meetings this next year.

John Cook

Chatting with John Cook of GeekWire during our Founders RAW conversation.

Ask The Right Question At The Right Time

There are certain moments, typically in business development conversations, when you sense the entire future of your company is resting on that exact moment in time.  You realize what you say next will either result in an affirmative commitment to your company or a “thanks but no thanks” response.

I just had one of those and boy and I glad I knew it was happening.

The conversation was with a self-identified skeptic for which they were asking why they should consider working with Seconds.  This individual was very cordial and nice, yet opened the conversation with an obvious “you’re behind the 8-ball” tone.  It was up to me to unravel where they were coming from, identify where we fill the gaps and bring them to a point where they wanted to work with us.

I learned (or maybe realized) a few lessons as we were working our way through the conversation towards an agreement.

1.  No is easier than yes

People are naturally programmed to say no.  You must work towards the yes, which requires taking that person on a journey through why they are better off with your solution than not.  Saying yes requires one to actually commit to something.  Saying no requires no commitment, thus it is the easier option.  Remember, most people are commitment phobes and would rather say no than have to stick to a commitment.

2.  Conversations turn with one question

As we worked through our conversation and they received answers to all their questions, it became apparent to me I needed to take control of the conversation if I was going to get a satisfactory outcome.  At one point they mentioned they were already working with a “somewhat similar” company, and asked why they should consider working with Seconds?  My response… “how’s that working out?” and then waited for the answer.  I followed up with “are they rolling out nationwide with your organization being the only organization involved, meaning your organization will be highlighted and singled out?”

At that moment, the conversation changed.  It became clear there was no logical reason for this person to say no and we started down a very positive brainstorm on how to make our partnership even better.

3.  People need to be led

What this really comes down to is the fact that most people just need to be led to a decision.  Since people are programmed to say no – even when yes is the better answer – they need to be led to understand why yes is the better answer.  This takes courage for sure, because going out on a limb and calling someone out can be risky, they might get upset and you might even lose the opportunity.  Yet, it may be the only way you earn a new customer or distribution partnership.

You can learn a lot from one conversation, next time pay attention to how you are handling the questions you are being asked.  You might just help them help you.