Posts Tagged ‘Podcast’

220: Jason DeFillippo Grumpy Old Geeks & The Jordan Harbinger Show Podcast CoHost

Jason DeFillippo Grumpy Old Geeks & The Jordan Harbinger Show Podcast Co-Host Legends and Losers

What exactly is AI and why does everyone insist on using the term to cover a multitude of basic software? Jason DeFillippo of the Grumpy Old Geeks and The Jordan Harbinger Show joins us for today’s episode. He talks about tech trends and why the blockchain is the second coming of push.

“It’s an Excel spreadsheet that has track changes turned on that everybody has access to.” –  Jason DeFillippo on the blockchain

Three Things We Learned

Grumpy Old Geeks vs The Jordan Harbinger Show

Jason is having the time of his life being part of two shows that infinitely differ but also share similarities. Grumpy Old Geeks is the show for tech veterans who have seen it all and want to get a few kicks by making fun of new tech. The Jordan Harbinger Show is a cerebral podcast that challenges its listeners and guests to think.

Marimba, PointCast, and Blockchain

Jason has seen a lot of things over his twenty-something years in the tech sphere. Among these is the quick rise and even quicker downfall of the enterprise and consumer versions of the push software: Marimba and PointCast. According to Jason, this trend is visible in today’s second coming of push: the blockchain.

AI: Fancy name for basic software

Blockchain is right on the heels of AI, the ambiguous term everyone uses to call a bunch of software that run through basic machine learning and algorithms that make it pretty difficult to enjoy the Internet. This term was coined long before actual software deserving of the moniker began to exist. And even then, the programs are pretty far off what the sci-fi novels had planted in our brains.

New tech turn up fast. But the trends are there, and they’re almost always bound to be true. If Jason’s informed guesses are correct, then it’s not too much of a stretch to claim that sooner or later, AI and blockchain will meet the same fate as their predecessors.


Jason is a full-time podcast producer and editor for The Jordan Harbinger Show. He is also  the Creator and Co-host of the Grumpy Old Geeks Podcast.

Jason has been building websites since the early days in 1994 for clients that range from small businesses to million dollar websites for blockbuster films to his own start-ups.

In 1994, he created the groundbreaking website Spewww which was nominated for a Webby in the first year the awards were held in 1998.

In 1995, a new media company in Santa Monica moved him out to Los Angeles to build the first website for Epson America.

Since then, Jason has launched over 250 websites for major corporations like Paramount Pictures, Sony, Warner Brothers, and Disney.

He also created the two time SXSW Weblog Award winning Blogrolling service as well as co-founded the global blog network Metroblogging.

He has worked at several startups in San Francisco including Technorati and 8020 Media, the publishers of, and statistical aggregator Metricly.






Grumpy Old Geeks – Website

The Jordan Harbinger Show – Website

We hope you enjoyed Jason DeFillippo on this episode of Legends and Losers! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe on iTunes!

202: Legends and Losers Unlocked Go Ugly Early

Legends and Losers Unlocked Go Ugly Early

On Episode 183, multi-time Silicon Valley CEO Jay Larson joined Christopher Lochhead in a dialogue that left many impressions. An executive admired by a lot of people in the marketing sphere, he said some amazing tidbits that until now Christopher looks back on. Today, the host mulls over some of the most resounding words left by the CEO of red-hot company Optimizely—to go ugly early.

In the sage words of Jay Larson, when you have bad news, go ugly early.” – Christopher Lochhead

Jay Larson – Getting to the Ugly Early

This advice is exactly the opposite of what most people would think when they have bad news waiting to be unveiled. Anyone can be guilty of delaying the inevitable, be it a CEO or a politician.

When there’s bad news and they have to go on TV, they would most probably go on about things that may not be relevant to the real issue. They meander around and try to remind people about how great they are before dropping the bomb.

Undermining Yourself

When you fall prey to the bad news and don’t put it right on the table, you communicate to everybody that you’re not on top of it. You fail to be professional, unable to show that you have a grasp of the facts.

It doesn’t matter whether you are an entrepreneur, a CEO of a company or a leader of any kind. Not dealing with and resolving a bad news upfront mean undercutting your power.

Facing the Ugly Head-on

Dishing out the good news before the bad is a disservice to both you and your constituents. This doesn’t help address the problem at all, and it reflects badly on your leadership skills and ability to manage a business situation.

By being honest with the status of your business, you will be braver in fixing the problem, and so will everyone around you. So go ugly early.

Listen and download to the episode now!

Bio / Links:

Jay Larson started in sales in Oracle and Siebel. He became Head of WW Field ops at Mercury Interactive, Head of Sales at SuccessFactors, President of Jive, CEO of Birst. And now, the CEO of red-hot Optimizely.

We hope you enjoyed this episode of  Legends and Losers Unlocked Go Ugly Early! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe on iTunes!

200: Jaime Jay Trading Legendary Stories

Jaime Jay Trading Legendary Stories Legends and Losers

Legends and Losers has always aspired to capture lightning in a bottle and be a podcast unlike any other while adding value to people’s lives. But this show is as silly as it is plentiful of knowledge. On this 200th episode, Christopher Lochhead and Jaime Jay trade stories both ridiculous and legendary.

“Get out and experience life a little bit.” – Jaime Jay

Jaime Jay – Crazy Airplane Tales

Some airline has finally come up with an addition to their business class seats that passengers wouldn’t want to miss—pillow menus. This successfully reinvents the word, “chillax”. People can now pick their preferred travel companion from a wide array of pillows and cases.

In the true spirit of airplane anecdotes, Jaime also shares an oily plane story involving a woman with a bouffant do and the greasy spot unfortunately branded on a plane seat.

Befriending Your UNI

When it gets lonely, people can turn to UNI. A magic AI friend, UNI can be your companion one tap away. UNI can do anything from chatting to dancing, and while it’s terrible, the UNI phenomenon is something we can all learn from.

Business Buzzwords to Kill

Some business buzzwords deserve to die in 2018. While they have revolutionized the sphere, some have become obsolete. This not only springs from a creative standpoint, but also from the fact that language constantly evolves.

Solution, for example, is a word everybody uses but is hardly ever meaningful anymore.

“Solution—I hate that word… Whenever I think to say ‘solution’, I check myself and I try to think about another word that I can use that’s more meaningful and identifies whatever it is I’m talking about rather than just vague, old ‘solution’.” – Jaime Jay

To hear more incredulous stories and why words like ‘disrupt’ and ‘solution’ should be considered throwaways from Jaime Jay and Christopher Lochhead, download and listen to the episode!


Jaime Jay (twitter: @heyjaimejay)

Jaime Jay is the Managing Director of Bottleneck Virtual Assistants, a Life & Business Coach, host of the popular Stop Riding The Pine Podcast, and co-producer of “dialogue podcast” “Legends & Losers”.

199 Questions and Cocktails #1

Questions and Cocktails with Christopher Lochhead 1
In this first episode of Questions and Cocktails 1, Christopher Lochhead answers questions from his legendary listeners. People from different walks of life send in their emails, and Christopher dishes out some unfiltered pieces of advice.

“Like in anything, most people quit. And if you wanna be successful, you gotta stick to it.” – Christopher Lochhead on staying true to your podcast’s brand

Young Professionals in an Aging World

Aaron, a Doctorate of Pharmacy and MBA student shares how listening to a tech industry podcast has offered him a different perspective of his own niche. Bloated with inefficiencies, his industry has seen zero progress in innovations. In a field where earning tenure means respect, he and other young professionals struggle to be taken seriously.
How can young professionals with an entrepreneurial spirit gather the respect to have the real conversations and cause change in an industry run by older people?
“Don’t let anyone stop you from bringing your ideas forward. There are some older people in business who do stay curious. They are open, they will be your allies.” – Christopher Lochhead

Starting a Podcast

An anonymous listener who once heard Christopher guest in Jordan Harbinger’s show seeks advice on how to start their own podcast. After years of being a chef and handling different food establishments and services, they are now ready to express themselves in some other way. They hope to bring more light to what they do beyond glorified social media posts on success.
Christopher gives a couple of tips on how to launch a successful podcast. He suggests getting a producer and editor to deal with the technical aspect of podcasting and building a brand that reflects both the personality of the host and their vision.
To learn more from Christopher in this edition of Questions and Cocktails 1, listen to the episode now!


We hope you enjoyed Questions and Cocktails 1.  Remember, Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe to Legends and Losers on iTunes!