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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.”

SJ31 – Tech and Entrepreneurship in Africa with Mannie T’Chawi and Jason Israel

We were honored to have two very special guests on Startup Jab this week: Mannie T’Chawi and Jason Israel joined us to talk about tech, entrepreneurship, and Africa.

Mannie T’Chawi is the co-founder & CEO of LayerCake; a social enterprise that promotes financial inclusivity and security in Tanzania. He also serves as the Director of International Outreach and Business Development for CULTIVA Solutions, a DC-area education consultancy and brokerage. In addition, Mannie consults on international development efforts helping to strategize, execute, and build partnerships between US and Sub-saharan Africa based organizations.

Jason Israel is a dedicated public servant, naval officer, and educator with over 15 years of experience in military and civilian leadership positions at the federal, state, and local levels. Currently a Commander in the Navy Reserve, he recently deployed to the Combined Joint Task Force Horn of Africa where worked in Somalia toward a more stable and secure future for the east Africa region. Jason is passionate about educating and empowering youth to rise to their full potential and has spent his free time teaching and mentoring students in each community he’s lived. A native Marylander and resident of Baltimore, Jason served as Director for African Affairs for the National Security Council at the White House until earlier this year.


  • Mannie: “Thanks to the success of mobile banking platforms in Kenya, for example, Africa has started moving towards mobile banking, which is really mobile transfer. It’s the equivalent of having your money in Verizon or AT&T rather than a a bank… Mobile transfer works for people fairly well, but you can’t exclude banks from the process. There needs to be unity, and less friction, and [my company LayerCake] hopes to provide that… You’re allowing them an opportunity, in a predominantly cash-based economy, to actually grow their wealth and savings rather than it literally being cash under their mattress.”
  • Jason: “What Mannie’s doing is really the driving force behind the change that we want to see in Africa. It’s a great example of looking at the institutions, the strengths and weaknesses that are in the country, and trying to build the capacity of the local banks in order to confront a challenge that is uniquely Tanzanian.”
  • J: “One of the greatest parts of my jobs [at the National Security Council] was hearing all of these stories about what entrepreneurs are doing to solve these unique problems.”
  • M: “People don’t realize that there is a lot of entrepreneurial expertise already in the market… Africa is a market that has always been wrought with necessity and is full of inventors.”
  • M: “The strategy for winning in Africa, no matter the vertical or industry, is being the connective tissue.”
  • J: Regarding “brain drain,” “I think it’s a myth that it’s just, ‘I can make more money in New York or London, so I’m going to head there.’ There are a ton of talented people leaving [Africa], and either a nation lacks the capacity or desire [to keep them in the country], or there’s a corrupt reason where somebody’s getting some money to allow people to leave.”
  • M: “We don’t just need big, bold moves, but we need a lot of big, bold moves all at the same time.”


Some of the cool efforts going on in Africa:

And check out: Somali Entrepreneur Raises $100 Million For Money Transfer Startup WorldRemit

SJ30 – The Business of Narrative Podcasting with Wolf 359

This week, we’re pleased to welcome Gabriel Urbina and Zach Valenti from Wolf 359, a podcast about the advantages of floating, tiny and alone, in the middle of nowhere. A drama in the tradition of the Golden Age of Radio, Wolf 359’s bi-monthly episodes tell the story of Doug Eiffel, the communications officer for the U.S.S. Hephaestus Research Station, currently on Day 448 of its orbit around red dwarf star Wolf 359.

Join hosts Teague Hopkins and Jason Nellis to talk about how Gabriel and Zach bootstrapped a successful radio show, the art and science of narrative podcasting, and life in isolated, zero gravity conditions.

Links and Highlights

EPISODE 30. This podcast is no longer a spring chicken, folks.

Gabriel dreamed up a character who was monitoring a radio on a space station, and made the “fatal error” of sharing his idea on Facebook. Zach (a voice-over actor) saw on Facebook that a voice-over actor was needed for a one-man radio show. The rest is destiny.

Listen to the first three seasons of Wolf 359 here.

  • “We were both attracted to the idea of doing something together and getting it out there quickly.
  • “What’s great about the first season, when it was basically our moms listening, it gave us a lot of freedom… It took us about 10 episodes to figure out what worked and what the show wanted to be.”
  • “Our philosophy was, let’s put things out there, let’s see if it works, and then let’s polish… [but] it needs to be a certain level of quality.”
  • “A lot of the first few episodes were built on, ‘Hey, I did this guy a solid once.'”
  • “From day one, we wanted to put something out in the universe that people could look at, and so we could really establish ourselves [in our respective careers].”

Zach does “sensual voice-overs” for, which, according to Gabriel, is “exceedingly mature and tasteful and well thought-out.” We say, go try it and find out for yourself (and happy belated Valentine’s Day!).

  • “The biggest technical challenge is making it work when people are recording in different spaces and different rooms with different sound qualities… We eventually solved that by deciding that the people who are remote will always be heard through a kind of filter, an ‘in-universe’ reason for their voices to sound noticeably different than everyone else’s. It was a moment of, ‘we’re going to try to turn this bug into a feature.'”
  • “We are fearless about the weird things that we do… but we rarely, if ever, have the next move planned.”
  • “There are critical times where it’s like, ‘Zach, it is now time to turn the “make shit up” button on’ (or off).”
  • “There have been times when it’s been a choice between having a 13-episode second season and get our merchandise together, and it’s always felt better to focus on making more and better shows.”
  • “Focus on making something that YOU love. The one thing we found in our nerdy, off-center taste is that we’re not alone, so in making something that we love, we inadvertently made something that other people love. Focus on that, because you can control that.”
  • In the beginning, “we tried all kinds of guerrilla marketing tactics when it was just our best friends and their cat listening to us… We tried to do the stereotypical ‘growth hacking’ to create our online presence, and the effect that had was… nil.”

View replay on

This episode previously aired on Wednesday, 4/17/16, at 3:30pm ET

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

SJ28 – Aspire with Lily Cua and Marcy Humphrey

This week’s episode will introduce you to, software that helps companies make smart investments in their workplace perks so that they can recruit, engage and retain the best talent. Lily Cua, founder and COO of, and Marcy Humphrey, Head of Perk Operations, join Startup Jab to share how they are building Aspire, fill us in on the hippest, hottest HR trends, and tell us if office beer pong really is a good idea.

Lily focuses on Aspire’s client acquisition and expansion efforts. She is always keeping an eye out for unique and engaging workplace experiences to build into the Aspire platform, and loves the fact that her job allows her to work with some of the most innovative and creative businesses in the country. Lily is a graduate of Georgetown University and in a previous life was a consultant at PwC. Most importantly, she is a gifted arcade basketball player and brunch enthusiast.

Marcy is a graduate of Georgetown University, and has been in the DC area ever since. Marcy keeps the gears turning at Aspire by working in partner strategy & operations and managing client relationships. She also develops marketing content and is constantly looking for the coolest new HR trends to chat about. She counts among her many talents solving world hunger with Excel shortcuts and running faster than your average snail.

SJ27 – We Survived Snowzilla!

In this week’s episode, we tackled some big problems for brand-new startups, including how to get the right team to be in your corner, and figuring out what’s the real MVP.


After 27 episodes, it’s time to grow up a little bit. We’ve started adding special content for our podcast listeners, so if you’re not subscribed, it’s your time to shine. Do it!

Links and Highlights:

Quick hit: Are live sports and esports getting closer together? When will the cars be replaced with holograms?

Formula E announces 300kph ‘RoboRace’ championship

  • “It will be a testament to the cars’ software teams and hardware teams to create these vehicles that will compete at 300kph and have the computer driving the car.”
  • (First-person drone racing is a separate league, folks.)
  • “Eventually there will be the ‘you must have a human driver’ league and the unlimited league.”
  • “First, computers are driving, and then they’re taking over our basketball teams. Where does it end, Teague?”
  • “When driver-less cars become a thing, and none of us ever have to pay attention, the irony will be that we spend our time watching driver-less racing.”

It’s Quora Day!

How do you teach early-stage startups to use the Lean Startup methodology? (09:48)

  • “It’s pretty obvious that they haven’t solved customer-problem fit yet, but they believe they have.”
  • Unless you’ve done the proper research, you may created a solution and now you have to back it in to a problem. That’s not how Lean works.
  • “Almost anyone who’s been an entrepreneur has had this exact experience, where you’re like, omg, this is amazing, we built a cool tool, we’ve launched it, and… nothing, because you don’t know who you’re solving a problem for, you haven’t articulated the problem in a way that makes sense to them.”
  • The bigger challenge may be when people have something that sounds logical, but they haven’t actually validated anything by talking to people who would actually buy it.
  • Mike Tyson said, “Everyone has a plan until they get punched in the fact.” The way to really help a start-up in this situation is to have them get punched in the face as quickly as possible.

Is there such a thing as an MVP for a luxury fashion startup? (22:15)

  • “I hate the term MVP, because it gets mis-used so often. What are we actually saying? Are we talking about a small run of a physical product, designing a website that can sell this stuff… What’s the actual experiment we’re running?”
  • “Branding is something that is more difficult to experiment with because there are fewer signals and it’s harder to separate out cause and effect. You can do five different things to try to build your brand, but you can’t necessarily separate out the effect of each of those things on building the brand.”
  • “A ‘minimally-loved product’ might be a better thing to try to reach. What is the thing you’re going to build that people will actually really enjoy? And then build the brand around that.”
  • The problem you’re solving might be an emotional problem. Do customers what to be seen as youthful, as adventurous? What’s the emotional need that this luxury brand is trying to fulfill? You can’t invent a brand that’s a luxury brand overnight, you have to grow it, like a tree.

What is the best way to organize technology startup company in terms of projects? (32:35)

Teague gives a broad overview of organizational design in 10 minutes, which is SUPER impressive.

  • “From a design perspective, you want to make sure you have separation of certain characteristics. You don’t want to have any function that is tasked with efficiency reporting to any function that is tasked with effectiveness or vice versa, because you’ll end up having them lead together.”
  • “You don’t want to have short-term focused groups reporting to the same folks as long-term strategic initiatives, because almost always the long-term will be in service to the short-term.”
  • “In any good growing culture, you’re going to hit walls and snags. That’s not the problem. It’s addressing them and fixing them, and if you don’t, that’s the problem.”

As an entrepreneur how do you know when you have the right team in your corner? (40:02)

  • “I know I have the right team when I stop worrying about the team.”
  • “You run into a lot of problems where you have a team where everyone thinks the same thing. Diversity leads to better decisions, and you want those decisions to surface to the manager level. and discussions are happening in a way that you get involved in them and can see both sides of it… Hiring for diversity is a great way to make sure you have people with ‘strong beliefs, loosely held.’”
  • In companies where the benchmark for cultural fit is “We know it when we see it,” it can be damaging because people end up hiring people who look like them.
  • “We talk about how culture is top-down, it’s in-out… You are as responsible to your team as they are to you, and you may have the right team in place and not know it because you were so wrapped up in your own crap that you missed the signs. When you’re a founder of a startup, it’s incumbent on you to recognize these things in advance.”

Live question from Mr. Wonderful: Who is your dream client?

Jason’s dream client is anyone who wants to give him “a lot of money and very little work to do for it.” (Just kidding. We think.)

Time to work together: Let’s get Gary Vaynerchuk on the show!



This episode previously aired on 1/28 at 3 pm ET/12 pm PT

SJ26 – The Healthy Uncomfortable and Scaling Your Startup

a.k.a. “We Promise It Won’t Be Boring”

Don’t miss our latest round-up episode, answering your questions, expounding on your conversation starters, and delivering David Bowie tributes. We may also have snuck in some Alan Rickman references.

Still want to join in? Send us your thoughts on how this quote applies to you:

“All my big mistakes are when I try to second-guess or please an audience. My work is always stronger when I get very selfish about it.” – David Bowie, The Word, 2003

Previously aired on 1/19 at 3 pm ET/12 pm PT

Links and Highlights:

Teague as a blonde? The end of the world? There’s a lot going on this week.

The Healthy Uncomfortable

  • “There’s somewhere in between the comfort zone and the terror zone, where you have to have some courage to try the new thing.”
  • New t-shirt idea: “No matter the question, time-boxing is the answer.”
  • “The question to ask oneself is, ‘What are the ways in which I’m intentionally making myself uncomfortable?'”
  • “Being vulnerable over being polished holds people back the most…. If you don’t feel safe in vulnerability, you’re never going to make any changes or push in any uncomfortable directions.” Also known as: “I get knocked down, I get up again. You’re never going to keep me down.”

Advice for early-stage entrepreneurs and start-ups in the scaling phase:

  • “In addressing an entrepreneur’s most important early-stage question – customer acquisition – it’s easy to waste a lot of money in the wrong channels, especially if you’re not taking a measured approach… How do you know if a channel is working for you or not?”
  • “You can Lean Startup your way through that question by being methodical about it and keeping the costs low by doing it on a pragmatic level. If someone’s selling clothes, for example, I’d go out with 25 t-shirts and see if 25 people will buy them.”
  • “We’re not getting scientific proof; we’re getting down to, ‘Is moving forward on this product or business a reasonable bet to make?'”
  • “Do you have the kind of business that can be advertised, or does it have to be pounding the pavement? Customer acquisitions costs are different depending on the industry.”
  • “Customer acquisition costs will change in different channels all the time, and you have to know when there are diminishing returns in those channels.”

Jason is sharing the story of Mostafa Hassoun, a 23-year-old Syrian refugee now in Annapolis who is hoping to enroll in community college. Take a moment to learn more about him and consider donating to help him rebuild his life after experiencing great tragedy:


SJ25 – Bonus: The Future of Esports

For our favorite subscribers ONLY. (That’s you!) Check out our mini-episode (mepisode?) on a future renaissance for esports. And don’t forget to send us your comments and questions in the mailbag.

Links and Highlights:

  • Teague is officially the Droid to Jason’s iPhone. (We all knew that already, though, right?)

EA sets up Competitive Gaming Division

  • “We’re always going to be dependent on the developers to support esports, because you have to add features like the ability to spectate and make it an experience for the viewers.”

MLG sells “substantially all” assets to Activision Blizzard for $46 million, DiGiovanni replaced – eSports Observer

  • “There is some concern from players that when developers hold so much control over the entire vertical stack of an esport, there’s concern that they will try to milk it for as much money as it’s worth.”

Jason spends at least five minutes comparing esports to competitive hot dog eating. Send your letters to him here.

  • “It’s not that there’s a lack of skill in esports, but there’s a lack of athleticism.”
  • “Is marijuana a performance-enhancing drug when it comes to Halo?”

Facebook Just Held A Business Focused eSports Summit

  • “Facebook recognized that serving esports teams and developers and leagues is actually a lucrative enough business that they want to dedicate some resources to targeting that industry.”


SJ24 – Online Dating with Erika Gayle Ettin from A Little Nudge

Erika Gayle Ettin, founder of the dating service A Little Nudge, joined us to jab about the challenges of starting her business, advice for fellow entrepreneurs, and the economics & challenges of online dating.

A Little Nudge has been profiled on NPR, the Washington Post, WUSA9, and Erika is also JDate’s leading expert, has been a featured columnist on, and her weekly column is syndicated through the Chicago Tribune.

We had some technical issues, and the audio quality was not what we wanted, but the interview was great. Special thanks to Erika for her work making it happen!

Previously aired on January 12 at 1pm ET/10am PT