To Ask is to Seek Denial

Karl Jacob
4 min readJun 9, 2021

Untold Story Zero

I was scared, really scared

and tired since I had been up coding til 4am.

Today was the day I had been working toward for months.

It was my first job and I was about to demo my work to the CEO of the company Scott McNealy, a well known, hard charging, hockey playing guy who wasn’t known for being patient.

It was demo day for Sun Microsystems and I was one of many employees vying for the attention of senior management. Each of us was hoping their product would be chosen to be one the company would put their effort behind.

I had rehearsed, I had coded, I even put on a collared shirt and slacks for the big day.

The product was (at the time) revolutionary. An email client built from the ground up for mobile and wireless environments which had just started to emerge. We called it ROAM. The product was much easier to use (thanks to the ex-Apple team of Bob Glass, Tog and Jakob Nielsen) I had the pleasure of working with on the user interface. To top it all off it was blazing fast thanks to the amazing Bill Yeager co-creator of the IMAP protocol, about 3x faster than the existing product our customers used for email called mailtool.

Yeah, there was already competition and it was in the form of one of the largest product teams at Sun with a product that had been in market and dominated our customer base. Even every employee at Sun used mailtool.

I pitched my product to every manager I could find in the company and even the mailtool team, to no avail. No one wanted to hear about something new or different. Mailtool was “just fine” even though it was brutally slow and would never work in the wireless world that was coming.

There he was Scott McNealy moving slowly, laughing, frowning and giving his shrewd and pointed feedback to people demoing their products.

He was one table away… I gave the demo one last test, straightened my shirt, took a deep breath and braced myself. He strode up and smiled, shook my hand and said “lets see it” My pitch was on, the product worked flawlessly and Scott nodded and smiled at many points. Finally the demo was over and silence hung in the air…

Scott said “Okay when does it ship”

I was shocked Ship? I couldn’t even get anyone to listen to me much less ship my product.

I launched into all the excuses, the frustration with management everything. This was my chance and I was going to lay it all on the line.

“Scott I keep telling people it’s so much better and asking them to help me and no one will lift a finger!”

Scott smiles, puts his hand on my shoulder and squeezes My body tenses ready for the bad news and he says…

“Karl, to ask is to seek denial”

He releases his grip and ambles away.

I was dumbfounded wtf did that mean??? “To ask is to seek denial?!??!”

Later that evening as I tossed and turned it finally hit me Scott had given me exactly what I needed but I didn’t know it.

I redoubled my efforts. I wouldn’t ask anymore I wouldn’t take no for answer and sure enough when the final decision came Scott backed me shipping the product I had labored on for so long.

A couple years later the product we created was shipped on every computer Sun shipped and customers all over the world used it every day.

While I had always considered being an entrepreneur it was that fateful day when Scott uttered the words “To ask is to seek denial” that I started on my journey. 7 companies later and countless battles won, some lost and millions of people helped I reflect back on that moment and realize that when you stop looking for permission to do things from others you take the first step on your entrepreneurial journey

Moral of the story, if you want to be an entrepreneur stop asking for permission just do it!

Hope you will join me for more untold stories from my journey as an entrepreneur and some from others as well

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