Author Archive | Teague Hopkins

SJ33 – The Importance of Stepping Away

We’re back from our quasi-planned hiatus, and delving deep inside Jason’s mind as he plans an even bigger break to process existential issues, walk hundreds of miles, and eat lots of food. We also talk external validation and intrinsic motivation.

Jason’s not leaving quite yet, which gives us some time to find a guest host before he does. Submissions welcome.

On the other hand, our producer, Katie, is on break now, and in the absence of her fantastic show notes and quality control, you get some hilariously bad machine transcription. [Help us.]

Robot Transcript

WELCOME TO START OF JAD.  Today we are going to take a trip inside Jason’s mind and figure out what causes him to make these crazy decisions.  With his life.  You know it’s a little messy in there.  I probably should clean up that from some leftover beer bottles from porches past those those those go on there was like that without a doubt you are welcome to start up jab.  Hello ladies and gentlemen welcome to Episode thirty three.  Of start of chat.  I am one of your host Jason Ellis with me as always the.  Well let’s just call it what it is the.  Six o’clock to minute and.  T. got pins.  T..  How I am a trend.  Is that you know old.  Or I have or will definitely more beard.  OK.  Without a doubt.  Yeah.  You know I have a patchy sad beard.  That.  I would wish upon anybody.  Whereas yours is full and normal like a.  And I don’t now.  You know.  And I shaved it when I was in Puerto Rico.  You can’t miss yes.  Well we’re.  We’re back after a brief hiatus between vacations and trips to South by Southwest and all manner of ridiculousness in between.  What’s been an interesting couple of weeks.  All.  Here in the U.S. And this.  You have gotten yourself into some interesting.  Future plans.  Yes and in the I guess we shared which type of thing that absolutely.  Yeah.  What team is alluding to is that after some discussion and.  Some introspection I’ve actually decided that after two.  Two years of overachiever and.  Depending on how you interpret it six months of my.  Merger.  Is brilliant.  I decided to step away.  And do some travel and start to figure out.  I don’t.  I don’t want to call it I guess my next phase.  I think earlier for do it is as.  Applying a.  A punctuation mark on this part.  Feels about right.  I think.  Not so much of it’s a semicolon or a comma are period or what but it’s.  Yeah certainly a question mark.  Yeah.  It’s my favorite touch indeed.  Yeah I so.  I don’t even know where to begin but I guess I’ll start by talking about that.  You know.  I actually like a preface by saying that this has nothing to do with brilliant as a company.  I think it’s actually very important that I take a moment and actually.  Preface the whole thing by saying that this isn’t a reflection of my feelings on the company or where it’s been.  This is entirely selfish.  You’re not just flipping tables and being like yeah.  No I mean even if I did feel that way.  I would probably be limited to more of a well we just decided to go our separate ways or some other coded phrase like that.  No.  I have a tremendous amount of respect for the work they’re doing and I think anybody who’s listening.  Who you know.  Is looking for marketing support or.  Designer technology products help people to go to.  But it was interesting you know we heard.  The company.  The two companies together.  Towards the end of last year.  And in the last couple months it’s been the kind of thing that is just doesn’t quite fit.  So I start to think about why it doesn’t fit and I start to think about why.  I’m not happy.  You know getting up in the morning and having that.  Pin your stomach feeling is not healthy.  And I was having them a lot.  So I started to think about it and started to give it some serious consideration.  You know.  And over time.  I just realized that I wasn’t happy because I wasn’t happy that it was me.  Wasn’t the day to day.  It just was me.  So yeah I don’t know.  It’s an interesting thing to realize that your the problem.  Well.  Or I wouldn’t necessarily say you’re the problem.  Just that you discovered it wasn’t good.  Yeah.  I think that’s the end.  Not necessarily know what is a good fit nap and you’ve got some.  Something’s coming up to give you some space to think you know that some exciting plan.  Absolutely take some time travel I’m very very fortunate that I have saved money and invested well and I have nuff you know.  It’s not to fuck you money by any stretch the imagination but it’s fuck around money.  But yet.  Somebody who is in his early thirty’s.  You know.  Unattached.  No mortgage.  No kids no dog.  I can travel.  I can take time I can reflect.  So yeah I’m going to take some time.  I’ve booked myself a lovely little trip to Italy.  Because I can figure out whether or not I love Italy.  And then sometime in June I’m going to walk the entirety all.  Five hundred miles of the Camino to Santiago.  Starting in France and being in something over there called the Stella and Spain.  Which should be in I think so yeah.  Well you.  You know part or the you.  You.  You hate a small portion of it.  Yeah about one hundred miles last year.  I guess it’s not such a small fortune.  Well now.  It’s a miles but it’s over a week and it’s an average of forty miles a day if it.  It’s a Prius Yeah yeah.  Drink if you want it.  It’s about time at the side it works.  Yeah now.  And then thinking like a drink I think up walking slightly more than that because of its you know church or.  Random Walk.  Yeah.  Truckers walk Drunkard’s Walk.  Yet.  Yeah I think.  I think for me it’s.  It’s an opportunity to do some travel to see some things that will help shake up my viewpoints.  At the same time I’m not you know going to City to.  Aimlessly wander.  I think the fact that I have a purpose every day.  A specific plan.  I don’t think it’s healthy for me to just take five weeks to sit on a beach.  I’m not the kind of person that can do that and get anything out of it other than boredom.  I’m super not good at that.  I do for a week.  Yeah.  I’ll do it Italy for a week.  Can’t do it for longer than that I could.  Well.  And I guess you know.  I can go sit on a beach especially if I had wife by the evenings because now.  Gets ideas you want that trigger.  Being on them and I knew my going to the beach for a few hours total.  Well I’ll be bringing an i Pad with I actually think I want to try recording some of it.  You know.  Here video or even podcast some of it long distance.  Should get the better yet part of the recorder.  And interview people.  You know why I like that idea.  I might do that because it is coming next is Jason spin off show for the start of Jack.  El Camino de has so little be spectacular.  Please call it a community house on.  I will not.  I will not let the in the Peruvian.  Quadrant of my family would cut.  If I did that ask use me.  Yeah I have and I think it’s going to be fun.  I think it’s going to be a good opportunity for introspection.  We talked about this.  Offline but.  One of the challenges that I’ve been facing in.  Thinking about this is that my career.  Has often been dictated by the ebbs and flows of.  Of external forces.  When I moved to L.A. when I was twenty three.  I fell into a job who.  Then I let you know that I lived there long enough to figure out some stuff and then I went to D.C. and I fell into a job at P.B.S. and I fell into consulting which became an agency and for the first time.  The real active choice in my career of merging my company.  Suddenly it doesn’t work it’s challenging it’s more challenging than I anticipated and it’s not the kind of challenging I can outsmart it’s.  It’s internal.  It’s hard.  It’s overwhelming and.  I think for me.  Coming on that coming up upon that challenge.  Really forced me to play consider.  So yeah.  Well.  You’re fortunate to have made smart decisions are the both of the use to be able to take some time to reconsider.  To step away and actually think about what.  You actually want to do instead of.  What is right in front of you.  As not.  You know I think.  Traces.  I think that’s exactly it.  I think it’s being more intentional I think it’s being more honest with myself.  I think that sort of job is a great example I you know this about when we talk for ages about.  Different creative projects that somebody might be interested in I’ve had in the back of my head for ages.  You know.  Doing interviews of people recording them.  Just.  I don’t know putting them to the world and I think this.  In many ways has become that.  But at the same time.  Why did it take me that long to figure that out.  You know.  I mean it’s not like a microphone cost that much and.  There’s tons of free software out there that we’re using right now.  You know.  It’s true.  Yeah I mean that’s up for it but it’s pretty cheap.  You know when my point.  Now I think I don’t know I mean do you feel this way.  Because I sometimes think that.  I look at a creative challenge and I either think it’s not worth the time or not worth the energy and then I realize that what I’m really doing is just.  Resisting myself that I’m just not.  I’m not you know in the War of Art.  Kind of fashion.  That I’m allowing the resistance of a challenge to win out before I even take.  Take it on yet totally.  Well and I and I also.  I get to.  You know wanting to do something but like particularly when it’s not your.  Your main project when you have a career and.  It’s like I went to the side project thing you think.  But.  Do I have the energy to like move that forward all the way towards to completion or structures.  Do you bother starting.  Yeah.  And that is a heart.  Hurdle to overcome and.  I think you know.  I have also thought about.  Pod cast before and it wasn’t really until we kind of stumbled into doing this one that we actually did something with it.  Yeah.  But you know.  We have it sitting at thirty three episodes as.  As this one goes at.  Yeah.  And I think you know there’s also some of that cropped up also in our in our hiatus which was semi planned.  Right we kind of you.  Oakland.  Yeah.  Sudoku intentional.  That was it was.  It was planned after the fact.  Yes.  But we sort of thought we were going to go straight through it and not have a break.  But just.  You know I was I was on vacation and you were at South by and then.  You know.  And just like.  Things sort of who kept.  Kept piling up and.  We we we kept it going for a little bit and then there was kind of a break there and.  During the break I was kind of.  I was thinking well you know.  Do I really want to like.  Push this for her or maybe I’ll maybe I’ll wait for her Jason and Katie to sort of like the next step forward.  And that was a lot like two days before I emailed you was like seven when I lived together because there was a slip.  But you know there’s there’s there’s something.  There’s something to it of of having a team to to share the load so that when you get when you get tired of working on something or somebody else to push unfortunate enough for you to get excited to share the bird.  Yeah it’s you know we could.  We could talk about.  Constructive interference here.  Make some great.  Physics analogies where.  Like you just have to avoid bottoming out if you average out the energy levels of the various people involved.  REGINALD.  To give you a look now for absolute Well you’re giving hand diagrams like anybody listening.  Because I’m trying to figure out what you think you’re conveying because nobody else can see it as somebody who is watching the hand gestures you’re making.  I don’t get it.  But it’s not.  I appreciate it I appreciate the larger metaphorical.  Image that you’re trying to generate physics.  Physics.  Not saying physics.  But physics.  I think I think you have something there.  I think.  I mean like anything else creative projects and.  Whether they’re for businesses or for personal or for.  I don’t know something in between.  I think it’s really hard to do it by yourself.  That is why a lot of writers go slowly insane when they’re stuck with your typewriter for ten hours a day by themselves.  I think that’s why I see them at Starbucks because it’s just the energy of other people around them.  Pushes them.  I don’t I don’t.  I don’t know what this will become.  In the future I don’t think you do either I don’t know that.  I mean I certainly don’t know what my careers will look like either.  But I know that I’m ready to start to actually take some of those questions head on.  I think for a lot of people.  That’s to heart.  The number of people that have come up to me after starting to have this conversation about well I’m stepping away and you know I’m exploring.  You know my.  But this is Partners a brilliant I’ve been nothing but supportive and said When you’re done and you figured out some of your stuff come back and have a conversation with us I mean they’ve been incredibly generous.  But the number of people that I have talked to about my little string of them about to experience like that.  Thank you Rick.  And I sort of walk about but the number of people that the number of people that I have talked to about this who have expressed.  You know how incredulous they feel.  You know how credulous they feel that their experience.  My experience will be.  Let me try that again.  They can’t understand how I can do it and they couldn’t do it themselves.  But their ideas here but they’re envious that I do.  Yeah yeah yeah we get that a good catch.  I think we are.  They were going to take a short break and then we’ll come back.  OK.  I can.  So we kick out about the room but we’re back now we’ve found another place to record this.  In this wonderful co-working space.  Indeed.  So it’s a challenge.  Of course this room is no better on the Echo than the other one but.  We’ll do our best.  You can.  E.Q. it out.  That’s a phrase.  Senators use room.  Fix and post a go at it with a live.  Yeah yeah.  What I was saying.  Before we got cut off in the last segment.  Was the.  I’m been surprised by the number of people who have come to me.  Overwhelmed and impressed at the same time at the prospect of mine leaving to go figure my stuff out.  Is going to be a better way to phrase that by the way figuring out my stuff sounds like.  I’m you know.  I’ve got like a puzzle I need to figure out.  I think in reality it’s more teens and time to just be self centered.  Just thinking through what I want the process to process to do to help.  Yeah I think you’re right that.  They’re describing it as a puzzle.  As something to be solved.  Right is a very different.  Orientation.  Than that.  I’m going to take some time to.  You know just.  Process what’s going on and figure out where my next step is.  I think a lot of people.  I think a lot of people in their own mind.  Phrase these kinds of moments as problems.  And thus they need solutions.  Yeah and I don’t know that I feel that way.  Yeah.  For event that jazz is quite loud and I don’t know if you guys can hear you over the weekend it’s good.  It’s like jazz.  Well you know.  This is.  This is the joys of of colocated recording.  Indeed.  I think.  The one point and.  I was trying to make was that.  I’m bothered by the number of people that look at what I’m doing and it seems special.  Because that.  That depresses me a little bit.  It makes me a little bit sad that we live in a society that is what it looks upon.  As you called a punctuation right these moments that we define the end of things the beginnings of.  Of others or even the state of the spaces in between let’s call it as something that is almost mythic.  Yeah.  You know it’s something that’s the stuff of stories and everybody keeps referring to is my Eat Pray Love.  And I was going say it’s the hero’s journey.  Sure.  Yeah.  Same deal.  For me it’s like a deeper love is just really eating meat.  Because you.  Eat eat eat all that and you know the thing that well I mean you know.  Italy and Spain.  How could you not.  Honestly if I come back from if I don’t come back from the Camino still ten pounds heavier than I started.  I’ll have done something magical.  Because that’s the advantage of doing can you know there’s you walk your five hundred miles an every thing along the way.  You know now.  Yeah.  Yeah.  Well.  My movie to be a little bit more restrained so that I am.  Thinner than when I started but yes absolutely.  You know I don’t know I it.  It bothers me a little bit that people.  I don’t think that what I’m doing is particularly special.  And I think that what I’m doing is particularly unique.  I think that most people just don’t give themselves the permission or.  They don’t give themselves remission when the time is right to take these moments.  Or.  They feel so encountered by their lives and the responsibilities of their lives.  That they don’t recognize that there are ways of doing it within those parameters.  So that next meeting of a couple the things one is you know we.  You did mention already that like you.  You are in a position to do this you’re single your own mortgage your kids your have.  You know obligations and you can sort of just like think of it go.  Right.  And I think what you’re sort of alluding to is that like.  Even if you had some of those things that were there would be a way for you to do part of this right you make sure you might not take you know.  Two months ago.  Five hundred miles in Spain where you can have some kind of punctuation some kind of.  Retreat to step away.  Even if it was just for a weekend or for a week.  You know to give yourself the space to.  Process some of what’s going on and figure out why you’re not happy in your current job and figure out what the next step might look like absolutely.  I think the process of self reflection of.  You know.  Of of self understanding is something that particularly the world of.  You know business.  And just the way that people whether it’s start ups or growth companies or people.  You know.  Planting their.  You know flags somewhere and building their thing on top of that people don’t give themselves enough space.  Yes you know get it so I mean.  I’m done and I’m saying this by the way not like I’m some.  You know.  You know wise man on top of a mountain like I’m dispensing advice like I can.  I’ve done this for ages and I’m I’m just figuring this crap out.  But I you know the fact that I’ve been since I was twenty three.  Working virtually nonstop.  With the exception of moving from L.A. where.  As soon as I got here I started job hunting.  I have some perspective on this.  Yeah I think it’s a.  It’s a process that.  As you said it’s not a problem to be solved it’s.  It’s an ongoing exploration.  Right.  This is the.  The process of self discovery and of living a mindful life.  Is is not one of the few like the phrase.  A mindful life.  You know.  I’m not being sarcastic I’m one hundred percent serious.  It was just you know that’s that’s kind of that’s the orientation I come to you from that’s my.  That’s that’s my grounding and.  Yeah.  Well let me ask you a question because I mean you know and I’m not intending to put you on the spot of course but.  You know you’ve been thinking about the trajectory of your career you’ve been considering some of the options that are available to you.  What is your thought.  In your ability to do this kind of thing do you feel that this is totally off the table because of your responsibilities do you feel there’s a version that if you wanted it you could take.  So if you were putting out spots fine we just added up post.  No I think.  I I feel like I have done stuff like that in the past night.  Actually a lot of ways.  You know.  Business School.  With that person to some it was just sort of stepped out of my career and think about what I wanted to be take some steps towards doing that for a very very.  Degrees of success.  But I I don’t know I think.  I’ve always felt more like I wanted to.  To build a life where that was always an integral part of it.  And so that.  I want to feel like I don’t have to step away from it that I have this space in my day to day life to take time and take reflection.  You know I meditate most days.  And I find that to be really valuable really important to have that built in.  You know.  I think that that as a result sometimes I forget to take a vacation in the way that actually is a different thing and you know like that’s you know.  It was great to get away for a little while and it’s warm warm for a little while and having now.  Having now remember what that’s like and I take a few more vacation than I have in the last five years.  Easier after you take when you go you know if you do that again.  Yeah.  It’s not yeah.  That actually that actually was valuable and not as costly as I thought it was going to be.  Because you come back sort of refreshed and able to make a lot of progress.  On things that you know just kind of.  You know.  Slogging along with before.  Why I’ve often said that we’re.  As human beings we’re often.  You know.  Targeted your eyes off the prize.  And it results that we’re sort of inertia.  You know.  In terms of our energy that unless something external acts upon us to change direction we’re going to keep doing things for doing well and you can use that for.  You can take advantage of that or you can.  You can have to take advantage of you right.  And I think that’s kind of the.  Figuring out which one is which is a great.  You know great thing because you can manage to me you’re married.  OK.  But.  But your hair.  I know so I know.  I know I’ll post a picture sort of you can see how good it looks today.  Good Lord no.  I’m sorry.  I promise to be more modest in the nuts and about and that’s a lie right there.  Good sort of your son is going to you know sort of saying like.  We for instance.  Now it took thirty three Of start of job and kind of figuring out what we want to do with it in what direction we were taken in and we probably would not still be doing it if not for a little bit of inertia.  True.  Right I think we.  There’s there’s a level on which.  Having done it for.  You know every week for half a year or whatever.  It is easier to keep doing it than to stop doing it.  But there’s also been moments when we sort of thought about like you know what this is.  This is kind of a lot of work.  Maybe maybe it’s rough course.  Well.  But I also think that you and I.  In reflecting on this is the example I have right now to realize the times that actually.  The answer is necessarily to stop it’s also to shift gears.  We.  You know.  Find ways of making it simpler.  You know.  Our producer Katie Keenan helped us tremendously.  Times we have saluted.  And not to mention.  Excuse me.  Not to mention the.  You know what we hear from people that tell us it’s valuable that helps mean you know.  I think and in fact I actually think.  External.  You know.  External validation.  Is just as important as.  Internal desire.  When it comes at least not always but at least when it comes to.  You know.  Refreshing yourself.  To knowing that the things you do have impact on somebody other than yourself.  Has taught you in times.  So.  I think that.  External validation is an interesting what right does.  It is a powerful part of the questions maybe should it be I think to some degree what you’re getting out there is is.  You know there’s the internal.  Intrinsic motivation.  And then.  You know.  Extra factors do have an impact on what people want to continue doing things whether we want to continue doing things but.  But I think also there’s a thing you’re alluding to around.  The opportunity to serve.  Young.  Feeling like you’re actually helping people.  Is a reward in its self you know those people don’t give you anything for that help.  Right you and just being able to help people and feel like you’re contributing.  Value in some ways.  Is.  You know I think that boosts the intrinsic motivation.  Sure.  Well I think also that there’s.  I think that part of it may also be the.  Whether we want.  You know.  Back to the subject specifically of external validation.  Whether we want to be important to us or not is kind of not the issue for many people.  It is still important.  You know.  I think that we often.  I think we have to make decisions.  And the need somebody else to tell us that we’re on the right path.  Another That’s important for me.  Whether we should write.  Well and you can do me.  Should is a.  Is a more high level concept.  But there is a basic need for validation that many people experience.  Not everybody.  Some people are not enough where they actually don’t need somebody else to tell them it’s good enough or whatever but for the most part.  You make a decision like this.  You don’t want to rock the boat you don’t want to be seen is abnormal.  And you know.  It helps to get somebody to tell you know.  It’s good take the time.  I will absolutely confess that I talk to family I talk to friends I talk to my business partners.  I didn’t make a decision without making a decision with them.  So.  And I’ve no idea what that sound is sorry guys.  You’re going somewhere recording something you know.  Anyway.  For me.  I just really.  You know.  It’s important to me that in a moment like this.  I know that the decisions that I’m making.  You know other people’s experience are so off the beaten path.  So strange that I’m not setting myself up for failure sometimes because for me I look for the pitfalls.  There’s a lot going on in the background.  I go.  Yeah it’s like buildings coming down around us what was that.  To make that joke because we’ve had like three fire alarms in the last four business days it’s been a nightmare.  And I think that was just the garage door.  The might be it.  Anyway.  Roland through the floor will be sort of playing that game way too much.  Oh yeah yeah yeah.  Yeah.  Yeah.  Anyway whether you agree with that or not and I’m certainly happy to admit that that’s my.  My opinion probably flip flops back and forth about.  You know.  Validation internal or external The reality is too that.  Sometimes things just don’t work out.  And for me it wasn’t because I had business partners I didn’t like or because the business itself was failing or.  That we tried to do something and failed magnificently.  Sometimes it’s also that you just lose your taste for it.  And I think for me I lost my taste for it and found or maybe even found that it wasn’t my taste in the first place.  And just didn’t know it.  Yeah.  I can conceive.  Yes it’s.  Entrepreneurship is hard and if you’re not one hundred percent in love with what you’re doing it’s even harder when it’s maybe not worth continuing to do it if you know.  Actually let you know it because it’s.  Well.  I would clarify that.  Entrepreneurship is a concept.  You should absolutely and.  There’s always ways to find.  Oh yeah I know I’m so nice if you’re going to specifically if your business that you’re working on is not something that you’re still excited about and still like.  There’s you know.  I mean it’s not going to talk about the debt.  Right right push good debt but you push through the temporary right you have come up with the times I think you have a successful business that.  You verge with another business and then.  Now you’ve got through the deep you kind of decided.  Actually that’s not the gap I want to go through.  Right you’re going to go back to back to Dr Martin.  And I defer to if we do.  Yeah.  That’s a song you look at up some time.  But you.  You went to the same middle of high school this is a ninety day supply so you have to block it out.  Yeah you did.  Yeah you did.  I didn’t have your hair.  You know you keep saying that.  But you know.  If you just try to larger.  Soames that you just smile.  More but I really appreciate that there are a number of people that every time a pundit tells a we’re all a tissue I was smile more.  You know that four thousand people just down their gullets And I think it rightfully so yeah.  That’s exactly where I was going when you’re.  That up to the same thing.  Yes.  You know that’s totally why I probably don’t get some don’t want to see both their kids were there.  So you know I do it some point when I have a conversation about I want to find somebody in the politics realm.  I want to do a show about the craziness that has been this election.  I thought you were going to say you want to do a show about.  I’d like to do that too.  But they don’t have to be related.  Yeah.  Politics on a boat.  The sort of Jefferson.  Yeah.  Well.  This is been a fairly introspective episode.  Indeed.  And one full of.  Weird audio pops.  Yeah.  Maybe that’s maybe that’s a sign.  You know I think.  To wrap things up.  I’m excited.  I’m nervous.  I’m terribly nervous but I like the healthy kind of nervous you know like I really don’t know what’s coming and I’m I’m OK with that.  But it’s not keeping me up at night.  Or I go.  You know.  Since making this decision.  Deep in my stomach is disappear.  So that’s not a good sign I don’t know what it is.  Yeah.  Well we’re glad we’ve still got you for a few months before you disappear.  To the trail.  When you guest host.  Yeah.  Maybe Frank.  Maybe rial and Riley will be a great guest host.  Well hopefully we’ll be back on a regular schedule shortly.  And in the meantime team anybody wants to reach out to you should they reach out to you for this idea.  You should find me at start Job dot com or type in Stockholm.  Seventy S some you know just jump right on my calendar there’s a link on my website.  To grab some time to chat with me.  Sounds good.  And what about you Jason.  Well now.  Just hit me up at Twitter.  At Jason Ellis J S O and yell at us because really.  Now that I still own brilliant without the vowels doco thank you T.V..  You know I got a bunch of your L’s I’m probably going to be selling them.  Yeah.  Please.  Reach out to us I make sure sign up for our mailing list.  As our website and just say hello.  We love hearing from people and.  Your thoughts on Today show or others and what directions we should go in the future we’re always happy to hear.  Yeah if you want to stop doing the introspective thing just get back to answer questions will do that if you want to hear more about our deep thoughts and Jason from spring I will do that to you.  All righty.  See you next week.  Thanks for listening to us be a terror.  Very loud and very funny.  And he would have no concept of actually meeting conversation it would just be wisecracked after wisecracking maybe we won’t put that in the actual show.  OK.  Anyway.

SJ32 – How to Break Into the World of Startups

Time to take it back to the beginning! In the latest episode of Startup Jab, we answer some questions on how to get started in the world of start-ups, from soup to nuts, and what you need to know about this quickly-evolving industry. Start your engines.

Links and Highlights:

“I’ve won business plan competitions. What kind of jobs can I get?” (02:03)

  • “If you win business plan competitions and this stuff is embedded in your DNA, should you just dive right in?”
  • “If what you really enjoy is that early-stage stuff of doing customer validation and the early interviews and experiments, you may not be that excited about the company once you get to product-market fit.”
  • “Yeah, but Teague. THE MONEY.”
  • “It’s the myth of overnight success: Have idea. Build company. Sell to Facebook for $100M.”
  • “There are jobs where being able to move something forward when no one else believes in it is a valuable skill, and there are jobs where not being able to get other people to believe in it in the beginning is just doing to doom you to failure from the start.” Know yourself well enough to figure out which job is for you.

“Can parents be angel investors?” (11:25)

  • “Technically, sure… your friends, your other family, your professors, if they have the money. It’s not so much ‘can they be,’ but SHOULD they be?”
  • “Typically we talk about that as a friends and family round, as opposed to an angel round. With startup money being easier to come by in the last fives years, people have been raising larger rounds up front, but as we start to see a bit of price correction and startup funding becomes a little more scarce, we might see people going back to doing a friends and family round first, to prove the idea before you put it in front of an angel investor.”
  • “It can be really stressful if your business isn’t going well and you go home for Thanksgiving, and your uncle says, “SO. How are sales?”
  • “There’s an obligation to make sure friends and family know what they’re getting into.”

“How should I prepare for a Skype interview at a startup?” (19:35)

  • Have good lighting, check your sound, and DEFINITELY check your Internet connection.
  • “There’s nothing that will take you out of an interview more than technical glitches while you’re trying to have a conversation with someone who wants to hire you.”
  • “Get dressed up for the interview not necessarily because of how you will appear, but how it will make you feel… When you’re sitting at the desk, wearing your interview outfit, feeling confident and professional, you sound different and people pick up on that.”

“What are some options to work for myself, with low startup costs, as a college student?” (27:10)

  • In college, Jason and Teague both made beer money by fixing peoples’ internet at home and setting up VPNs for them and taking care of email problems and that kind of stuff. Air high five!
  • “Take a skill you already have and try to sell it. It will teach you about what people are willing to pay for.”
  • “The cost associated with a service business can be almost nothing, and you can start very small and decide how quickly and how much you want to grow it.”
  • “This is a great time in life when you have the least responsibility with the most freedom, and the risk is pretty low in terms of things that you start.”
  • Great resource for anyone wanting to start and keep their costs low: The $100 Startup by Chris Guillebeau
  • “Pick a business that will set you on a path to the things you want to do later in your career.”
  • “Failure is not actually good, but learning from it is good. Failing is NOT the goal.”

SJ29 – Sex, Innovation, and Morality for Startups

We’re living on the edge today: Jason and Teague are recording from the same location at WeWork Wonder Bread Factory.

Links and Highlights:

Let’s get ready to DROOOOOOONE.

Can drone racing become as big as eSports?

The Drone Racing League Wants to Be to Drones What the WWE Is to Wrestling

  • “Explosions and money are the center of any good venn diagram.”
  • “Like any other sport, there’s already a push to sensationalize it and ‘sexy’ it up… The sport is not even out of the hospital bassinet.”

Jason and Teague toss out a FREE BUSINESS IDEA for our listeners. If you steal it and launch it, please make us VIP customers, #kthx.

Renaissance Florence Was a Better Model for Innovation than Silicon Valley Is

  • “Today, folks are often thrown to the wolves in a lot of ways: sink or swim. It’s a lot harder to find the kind of support you once got, where someone said, ‘I’m going to pay your bills so you can go build things.'”
  • “There’s a reason we keep doing Shakespeare, and a reason we keep bringing up penicillin.”
  • “When you give a mind an opportunity to just be told, ‘go try something and don’t worry about failure,’ there’s real opportunity there… I don’t think potential trumps experience, but potential and experience should balance each other.”
  • “One of the great ways startups can get a leg up is by hiring people who punch above their weight; finding people who have enormous people who haven’t been given their shot yet.”

Zenefits Founder Resigns

  • “Is what you’re doing actually harming consumers or harming competition? Is there a problem with pushing those boundaries, whether that problem is purely legal or whether there’s a moral issue at stake?”
  • “In a lot of ways we have a culture that advocates for screwing up, sometimes intentionally breaking laws and regulations, and then just apologize for it, mea culpa, pay a fine, and move on.”
  • “The moral question is, who’s being hurt by the laws that you’re breaking?”
  • “Zenefits is the latest in a series of very public companies that have skirted laws and done things that they know are immoral, and as a culture, how okay are we with that?”

New startup aims to transfer people’s consciousness into artificial bodies so they can live forever – TechSpot

  • “This is the beginning of every schlocky sci-fi novel I’ve ever read. Every single one.” (Here’s the definition of schlocky, btw.)
  • “We’re talking about condemning ourselves to a ones and zeroes existence because we’re afraid of dying.”

Questions from Quora:

As a non-technical co-founder, what should I be looking for in my Tech Co-Founder in terms of traits, skills, etc?” – (40:55)

  • “I like having a drinking buddy.”
  • “You as the non-technical co-founder have to ask yourself what you’re really looking for. There are some non-tech co-founders who think they’re hiring a general contractor, the same way I’d hire someone renovate my kitchen, fix my bathroom, and paint my house… They have the perception that they’re bringing in a one-size-fits-all ‘tech’ person, and that’s a perception problem you have to get past first.”
  • “When you’re bringing in a co-founder, you’re not actually hiring them… It’s finding a technical co-founder to partner with, so can you partner with them?”
  • Finding someone who’s willing to work with you at all is actually a good start.

My prototype is done. I aim to take on clients from another country. Can I do this without actually being based there?” – (49:12)

  • “The answer is almost always, ‘yes it can.’ The question is, ‘should it be?’”
  • “What’s the value of building a product you can’t sell outside your door right now, unless you intend to move there eventually and go sell it, or you have a ground game you’re really confident in?”
  • The more layers between you and your customers, the slower the feedback loop will be.
  • “Getting someone to use a product is hard. Building it is comparatively easy.”

This episode previously aired on 2/10

SJ20 – Data & Digital Nomads with Andrew Conklin

We are joined by Andrew Conklin, founder of DC Nightowls, now DC2 Digital Nomads, a part of Data Community DC. We’ll also talk about ‘being a people person’, radical candor, and mindfulness in the workplace.

Originally aired December 15 at 3pm ET/12pm PT.


  • Andrew Conklin, Founder of Routeam and DC Nightowls



SJ19 – Man, It’s Cold Outside

Join us for a weekly roundup episode, and bring your questions for our open office hours format. Got a question you want answered, but can’t make it to the live show, or want to remain anonymous? Send us a letter for the mailbag.

A few topics covered in this episode: updates from our hosts, Apple’s design evolution, a new way to create addresses for anywhere in the world, employee engagement archetypes, and a deep dive into customer interviews thanks to a great user question.

Originally aired on December 8 at 3pm ET/12pm PT.


Apple is giving good design a bad name

3-word addresses for anywhere in the world

The Two Sides of Employee Engagement



SJ16 – Loving What You Do

We talk about National Entrepreneur’s Day, how to find that perfect co-founding team, and why no one cares how hard you work. We also took questions from the audience.

November 17 at 3pm ET/12am PT.


The Entrepreneurial Power of Embarrassment

National Entrepreneur’s Day

Nobody Cares How Hard You Work

Dunbar’s number

Ego Risk: Why Innovation Fails

Screw Finding Your Passion

Doctors Without Borders – Right Now

Doctors Without Borders – Donate



SJ15 – What Matters in the Beginning

We answered some questions from the mailbag and the chat and talked about motivation, organizational design, where to focus before you raise capital, resumes, and a few other topics.

Live on November 9 at 1pm EST/10am PST.


Reddit Startups:

The Reasons We Work:

12 reasons this is a terrible résumé for a mid-level employee:

How Funding Rounds Differ:

Where to Focus Before Raising Capital:

Can You Predict a Startup’s Success Based on the Concept Alone?:

Why You Should Not Have a President and COO:

How to Design Your Organization the Right Way:

College Students Aren’t The Only Ones Abusing Adderall:

And finally, Kiki’s lovely monologue:

To launch, or not to launch: that is the question. Whether tis nobler in the startup ecosystem to suffer the slings and arrows of outrageous employment or to take arms against that sea of troubles, and by opposing, startup?

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SJ14 – The Business of Comic Books with Steve Sunu

We talked about the business of comic books, and hundreds of you tuned in to listen. We talked about comics, movies, streaming, and nostalgia. There was a threat of an entire future show about Cowboys & Aliens, and a promise of an entire show about board games. Steve gave us the inside scoop on the comic books business, where the opportunities are for new innovations, and how you can make sure your favorite comics stick around.

Originally aired on November 3 at 3pm EDT/12pm PDT.


  • Steve Sunu, Formerly PR at Dark Horse Comics & Editor at Comic Book Resources


Why Homejoy Failed:

New Star Trek Series Premieres January 2017:

Image Comics:

Zodiac Startforce:

Scary Go Round:

Panel Syndicate:

Least I Could Do:

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SJ13 – Unicorns, Motivation, and Why We Work

Join us for lucky episode 13. We’ll talk a little about raising money, a little about motivation and why we work, and maybe a little Xbox and Barbie thrown in for good measure. We’ll also take questions from the audience and the mailbag.

Live on October 26 at 3pm EDT/12pm PDT.


  • Sol Weinreich, Co-Founder at MINR
  • Mike LaRosa, Co-Founder at Wayfarer Advisory Group


WeWork Used These Documents To Convince Investors It’s Worth Billions:

WeWork CEO: The best advice I ever got came from my wife:

After 59 years, Mattel gets it right: the new Barbie ad is awesome:

The paradoxical, pressure-filled quest to build a “personal brand”:

Xbox Elite Controller:

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SJ12 – The Business of Comedy with Brock Wilbur

We’ll be joined by award-winning comedian and writer Brock Wilbur of the Brock Party podcast. We’ll talk about the business of being funny, making a living as a comedian, why beards are the best, and maybe also chainsaws. His podcast has 10 times as many episodes as ours so he must know what he’s doing. We dare you not to laugh.

Join us live on October 21 at 1pm EDT/10am PDT.


  • Brock Wilbur, Host of Brock Party

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