I typically don’t share – but I feel compelled to do so today.  I’ve been following a guy Jason Calicanis since 2005. I’ve found his insight to the technology and startup industry helpful and inspiring.  Jason brings a “no Bullcrap” mentality to the table – nothing sugar-coated here.  If he has an opinion, trust me- you’ll get it good or bad. 

Can you remember a time when you were young, talking with your Grandfather, where he was giving you some piece of advice? That’s how I explain “who is Jason Calicanis” to my friends – he’s the great wise “Grandfather-type” for technology startups that you must listen to. (No, i’m not implying Jason is elderly, quite the opposite in fact!)

Jason has recently started the show “This Week in Startups”  where he will have a guest and talk about startups in general (the good, the ugly, how to get started, seriously great advice).

The latest episode of TWiST (#13) has the founder of 99designs.com and Sitepoint.com, Matt Mickiewicz.  I’ll be giving some highlights of the show in a moment — but not before you start your download of this episode so you can listen and amaze yourself right after reading this post. 

• This week’s show spends the first 17 minutes talking about some of Jason’s passions and contests he will be sponsoring.
• You’ll notice Tyler has a working microphone! Sounds like he’s still a little nervous… Hey Tyler: Relax dude! You’re doing fine – and you’ve got Jason right there to watch & learn from.
• Now we get into the guest this week, Matt Mickiewicz. Something to note about Matt – He’s a good speaker, great mind, and does not have a college degree (there is hope for those without a degree!).
• Onto the segment “Ask Jason”, which involves taking a live call. This can be interesting or boring depending on the caller. Both questions AND answers were great (You’ll need to download the podcast if you want the answers – I won’t spoil it here.)
• Jason’s Shark Tank is up next – here’s where it get’s reall intersting. This segment is where you’ll get to watch/hear someone pitch Jason & his guest – and the feedback from the pitch. If you think you have your pitch down, chances are you really don’t and that you’re making the same mistakes as the rest of us. This is totally one of the most important segments of the show.
• Guest Speaker up next. Just one spoiler here – on 99designs.com, Matt says folks are uploading a new design every 10 seconds.
• News segment (last part of the show). Covering what’s happened in the last week or so, with commentary.

Jason does a great job taking a subject and explaining in-depth while not overdoing it.  He also has a great knack for “reeling-in” a topic that’s just going nowhere or boring.  He’s simply a natural – and this really adds for the enjoyment in watching TWiST or any other show he’s a guest on (like This Week in Tech).

The popularity of having show sponsorship embedded into the show makes things flow nicely. However, consider what I’ve explained earlier about Jason’s personally style – he gets so excited about the products who sponsor him that the ad placements become borderline annoying.  

The bombardment of sponsorship throughout the show will not deter me, nor my inner-circle of friends from listening to Jason or watching the show.  Jason’s a very smart guy, who’s saying something interesting I want to hear about.  Jason’s passion for life, technology, and helping others shines brightly in every show.  That alone makes it worth watching over the boring network television or other crappy podcasts out there.

My rating for this episode is still going to get a full 5 stars.  There is so much great insight given here, for free, it’s very deserving to this full rating.

If you are looking for meaningful insight and discussion related to technology & startup companies (perhaps your own startup), you need to watch the show live (or listen as a podcast at a minimum). 

Still reading? You should be clicking over to This Week in STartups and get inspired.  Don’t hesitate. Don’t procrastinate.  Just go do it.

Links:

Read more information about Jason Calicanis and if you’re a real entrepreneur, follow him on Twitter @Jason

Website  This Week in Startups website (TWiST)

Jason’s human-powered search engine company, Mahalo

Related posts:

1. Real-time Search – OneRiot – on TWiST (This Week in Startups)
2. TWiST > This Week in Startups with guest Annie Duke
3. Gary Vaynerchuk – Crush It! Get serious insights in Business Now!