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Podcast Ep. 5: Building the Entrepreneur with Andrew Hutton


Show Notes:

00:09 - Welcome to the DesignerUp podcast

00:24 - Guest intro

01:13 - Andrew introduces himself

01:35 - What does the word entrepreneur mean to you?

05:18 - How Andrew got into the design world and teaching at Parsons school of Design

06:23- Brief stint at a pig farm in Uganda and introduction into social entrepreneurship

08:10 - Andrew's time at Accenture

09:11 - Teaching at Parsons School of Design

15:46 - Controlling inputs and outcomes

21:44 - Who is Day One for?

26:56 - Bootstrap vs VC path for entrepreneurs

30:00 - Learning by doing

34:50 - The importance of mindset and community

39:47 - Niching down and focusing

44:48 - The power of story as an entrepreneur

54:18 - What does balance look like to you?


Intro: Welcome to the designer up podcast helping you level up your product design skills and become a more mindful designer I'm your host Elizabeth Alli and this is Episode 5: Building the Entrepreneur with Andrew Hutton

Elizabeth: I'm very excited to have Andrew Hutton on the show with me today Andrew was a former adjunct professor at Parsons school of design in New York, he was a principal design strategist Accenture and the head of business design at Human Ventures he is currently the founder and CEO of Day One which is a cohort based program for entrepreneurs and idea stage startups. What I really resonate with about Day One is that it's not just focused on helping entrepreneurs that have their sites set on vc funding, it's really about starting businesses and creating livelihoods and about getting into the right mindsets that are really tantamount to success and longevity as a business owner or running a business and those are some of the things I'm really eager and excited to dive into with you today Andrew so thank you for being my guest

Andrew: Elizabeth thank you for having me um that was very well said my work is done no i'm really excited to dive into that and and yeah talk about all things where design meets business meets startups it's been a wild ride excited to to dig to it

Elizabeth: That's excellent so my first question is a very serious one how does it feel to say the word entrepreneur that many times a day.

Andrew: What's crazy is that i'm very good at typing it i know where the eu is ii i and all my keyboards know how to present it um it's a mouthful entrepreneurial um I don't know it stops meeting what it it starts just sounding like like noise um no it's it's fun to be able to just like live a day job where entrepreneurs and founders and every permutation thereof are the people i get to rub shoulders with and serve  and you know we get you know we're get past being like customers and they're just you know people that i'm working with and it's really a pleasure

Elizabeth: Yeah i mean entrepreneur it's an interesting word um the etymology comes from an old French word 'Entreprande' meaning to 'begin something' or to 'undertake' right and then it was adopted in English language and defined as one 'who organizes manages and assumes the risk of a business or enterprise' and then it also is related to the Sanskrit word 'anthraprena' which means self motivation so i think that's really interesting and really telling of what an entrepreneur is so what does that kind of mean to you and how did you find yourself as an entrepreneur

Andrew: Yeah i love that i love all three of those and really i love the two non-english translations right the undertaking is exactly right and i think there's that's much more pure and pure's maybe too strong of a word but it's much more the essence of what i think entrepreneurship really has always been and what it's really becoming so much more today i think you know we live on like micro time scales um but what's been happening in you know the world in 2020 now in 2021 um but also in the last five to ten years the you know rise of entrepreneurship the makers the creators the passion economies you know people just undertaking new things whether it's side hustles or whatever they might be um passion projects  these are all becoming much much much more legitimate entrepreneurial endeavors right so in many ways the word founder looks like put that to the side and yeah i i've been working with entrepreneurs for for a few years now um you know the transition for me was very much you know from a consultant coming from design school into consulting where um you know i was always doing both business consulting management consulting as well as design and  innovation work and it started to you know through that career journey dawn on me that entrepreneurs were always a little bit over there right because when you're consultants especially i where i was inside of a big agency big consultancy um doesn't quite feel entrepreneurial even though we're being innovative even though we're creating new things but entrepreneurs are always the ones doing the most down to earth at the bottom like it's pure is kind of the right word for it right there's there's no other you know things to get in the way you don't have to like please the the bosses or like play to the stakeholders you're just like i'm making a thing and if i'm selling it i'm i'm in the game right and if i'm not i'm going to make a new thing and oh it was so aspirational to be like entrepreneurs are the real innovators right entrepreneurs are and that's not to say anything  to the designers out there who are you know making and creating but um that was at least sort of a dawning on me and i can maybe go into that sort of like intellectual plus career journey of seeing entrepreneurship as this kind of force this power where innovation was being made and happening on the ground and yeah i love it in its most micro sense right i think entrepreneurship at the smallest form is the most like fun and the most like exciting yeah so how did you end up in like the design world and teaching at persons like where did you really kind of start getting into this innovation space yeah i'll even take it all the way back so okay out of undergrad um out of undergrad i got a economics and political science degree i was gonna go to law school i was all set i had taken the ls at twice i was accepted scholarships i got very lucky that i had interned as well at a law firm because you know i just go all in and it was the internship where i saw the sausage get made that turned me off and i had enough time togo through this whole cycle of like like a hype cycle of like i must be a lawyer to man i can't this is obviously not it i don't know what the answer is but it's not lawyering um and so if you've gone through your own quarter life crisis i'm with you it happens um sometimes it's for the best and most the time is for the best so um went through this very quick intellectual journey um i felt very proud of myself for making a big career decision at 22 in hindsight i was you know i don't know just putting my finger in the air i happen to take a stint this is again like i won't we won't spend much time at all deviating into this little story but i spent six months building a business in Uganda it was a farm it was an agricultural business i just basically went off the map with a friend to go build this business it was a social business and when i came back i'm literally that's how fast i'm going to talk about my pig farming in Uganda but when i came back i was like i have to have a career who makes stuff who makes stuff and i answered designers designers make sucks so i you know born and raised in Connecticut so i was like i'm going togo to New York so i'm either going to goto school in Pratt, i'm going to go go find the the school that will take me out of Pratt or  Parsons and i'm going to go find the design program that's closest to what i am which is a business guy and it just happened to be the Parsons strategic design program was probably the best fit for me but there was a great program at SVA around social entrepreneurship i'm sure there's other programs now at um SVA and Pratt and you know really all the other schools um have added business and design from what whichever side they came from yeah so i i lucked into it and parsons's amazing experience really introduced me to design thinking right that was the whole program so i really don't i mean designer is too much is a stretch for a title because design thinking strategic design i mean it's really problem solving and so me moving into consulting was very natural because that's kind of what i was leading myself towards what i was what i'm probably really was meant to do and i'm good at but being able to pull on these design you know what design thinking is these design capabilities these design mindsets of living through ambiguity thinking in divergent forms um creatively playing with many things before making decisions and um yeah it was an amazing journey within a big consulting firm Accenture to kind of find my own practice of where design design thinking met with you know one big business serving many other big businesses and and yeah there's so much to be said about that because my time at Accenture overlapped with a time when Accenture was buying all these design firms they acquired Fjord in my when i was there at the end of my time they acquired a bunch of smaller firms later bigger firms like Droga5 and it was very much parts of a evolution towards yeah we're gonna make design thinking part of our like consulting strategy and i felt like i lived through it so yeah it was uh i mean that takes me to my days at Human Ventures and consulting um consulting and startups and um in that big switch again from okay if designers make things innovators or rather entrepreneurs are like launching things i don't know it's like the next level right and uh and there was sort of like a push to get out there

Elizabeth: Yeah so how did you end up as a professor over at Parsons?

Andrew: I mean the very simple story is i got good enough grades in a class that they needed professors in after i graduated graduating you know from a grad degree in this not again new is the wrong word but in this kind of burgeoning field of strategic design design thinking i was as well suited as anybody to comeback and and teach it i was i went back and taught sort of the entry level class even in my master's program and yeah it was just an opportunity I couldn't say no to which was to put on my teaching hat again something that i think again that was fortuitous took the opportunity and have developed sort of that part of me and those skills because it has certainly played out in my throat through the rest of my career i love imparting knowledge and just asking that amazing question that just gets somebody thinking in a new way or just showing a something you know a data some piece of some piece of something that's inspirational and just kind of pushing people forward giving them assignments that push them out of their comfort zone so very fortuitous but found you know a groove there loved teaching basically always did that while i was at Accenture i was not going to give up that teaching post because i needed to keep my foot in the design worlds and just have some form of creativity while i was you know on sometimes pretty boring project

Elizabeth: So what year was that around that you were kind of teaching design thinking?

Andrew: That was graduated in 2014 so it's about 2014 through teaching design thinking working Accenture, doing all sorts of different things

Elizabeth: Well that was really early days for design thinking especially like applied to um digital product design and the stuff that we're doing now what kind of responses were you getting from students when you were teaching this kind of stuff like what was that experience of teaching this stuff like because it was it's kind of abstract and it's kind of weird and like empathy is something that's talked about so much now it's it's a really different conversation around it now but i would think that it was really different in those early days of

Andrew: Yeah any so the experience we had at Parsons was so Parsons is a design school teaching design thinking which i think is very different than you know Stanford teaching design thinking which is maybe Stanford's like business school perhaps right or all the programs that came up like when Toronto was doing it with um um Roger Martin or you know the way catalog has a you know a program now um being in design school people kind of came in knowing that like i actually taught a lot of designers i taught a lot of fashion designers and graphic artists people who were like good with their hands and needed to learn the other side of things the business side and so and so the idea of applying empathy towards a problem that wasn't like solved with your hand it was facilitated with these design mindsets and practices but it was a problem of you know applied to urban design or applied to business design or applied to yeah just entrepreneurship and i mean that was really where we had a lot of the rub right where people were mostly were more uncomfortable than not was applying was was yeah was just getting into the business world frankly right and and one of the things that we the parsons program did really well was basically say we're going to bite off these like big challenges you know half the students would bite off these like social challenges which is sort of the first thing that most people think of when they want to go like let's change the world you know wicked problems or solve climate change or poverty or something um but also just you know you know we'd bring in organizations that would bring their business challenges and um and they were very like holistic right okay we're gonna try to drive a business outcome we're gonna try to change this massive system now how do we go about it right how do we get how do we do the you know the kind of standard steps let's do research let's do sense making let's do some prototyping let's figure out where we're going right right um but yeah when it was applied to like we just had all these constraints of like so that sounds really great and maybe that could have been made great in design school but when you're when the real world of like a business proposition is in play it um you start to realize like oh that's actually a bad idea right and you just have all these different constraints i guess maybe that's one way to think about it right so designers design thinking is all about creativity within constraints yeah design thinking also just says our constraints involve technology they involve business viability right they involve users desirability right um yeah so i was really teaching those other two legs of the stool that were that were most uncomfortable and interesting for folks

Elizabeth: that's so interesting though our newsletter last week was titled what you want is control what you need is constraint because that's kind of something that a lot of new designers coming into our program have um struggled with they they often think of problem solving really from a visual perspective and kind of the elements that they're putting on the page and layouts and visual hierarchy and color and those types of problems visual problems but and they get into a space where they're often like presented with this blank canvas and they're just like i don't know what to dot here's endless possibilities i could put any color any button style any layout on this page and i really want control over what the users are going to do with this and how they're going to look at it and where the sight lines are going to be and then they forget or they don't know yet that they need to start defining their constraints right they're not going to have control over what the users think of their apps or their ideas or you know what they do with them even until they start going through these processes and you know understanding mental models and you know getting in the mindset of you know going through these iterative processes and then of course the business acumen that you have to have to be able to know what are the business constraints and then the technological acumen of what can the tech support just because you can make this amazing website with all of these you know parallax effects and the coolest fonts in the world if it can't load on someone's browser you know you're gonna have a big problem so defining those constraints more than feeling like you have control over this whole design thinking process is difficult for them

Andrew: Yes and what i was thinking along that whole train of thought was that why i think it's so important to bring entrepreneurship as a concept as a discipline into this dialogue is that entrepreneurship one way to define entrepreneurship is you basically so in the rest of the world whether it's designer the job you might have had in a big business or a consultant you control the inputs you control where things go on the page and that's what you're judged on you're judged on how beautiful that page looks or if you did all your you know reports right or if your financial model is perfect and you let the business take care of the outputs you know you've been given a job and you've nailed it that's like the world that's most people's world entrepreneurship flips the script yes you control the inputs but you are only judged on the outcomes you're only judged on if it does the job it needs to do and it has to load fast it has to be pleasing to the customer it has to make a buck you have to have someone buy it and you don't get to choose what your constraints are the market puts on you so the markets the customers expectations the competition whether your thing is cheap or expensive is not your decision right and so in some ways it's freeing because you actually don't get to choose where your constraints are but you better go find them you better understand what people are bringing to the table when they judge your thing and it's only in the eye of the be holder right success beauty whatever and it's it's it's a real mental shift because obviously you control the input so you're the entrepreneur you're the designer you get to decide if that button is blue or red or whatever but it kind of doesn't matter what you think it matters about the outcomes yea hand so when you get that mindset you get you obviously keep all your tools but the way you put them together changes you have to go find those constraints you have to go take your thing and get it into market you have to collide you have to ship and and then you have to iterate right because and you probably shouldn't even think that much about the first thing you do because it's probably wrong and regardless of and it literally doesn't matter what you think so this is like the Steve Blank school of thought and it's really true there's no information worth listening to inside of the building and that means your own opinion right so just get something built and ship it and and this is something that I've learned i did not quite you know you learn get out of the building in design school at Parsons wherever because you you learn research you learn empathy but you don't learn the necessity of your own opinions don't matter i mean you do because you learn empathy you learn like hey listen to that person treat thier experiences you know valid again don't they you do learn not to bring your bias but not in the way that like but what you are taught is to listen understand what the user is telling you and doing read between the lines you know don't don't do what they want don't build just what they want build what they need so you're taught that Steve Jobs kind of taught us that but then they're also taught sort of in Steve Jobs manner of like kick people out of the room and go build a beautiful thing right and i think most entrepreneurs Steve Jobs is an exception shouldn't really abide by that they should do all the listening and then just get the thing built and put it out there anyway i'm going on here but it's uh yeah it's very much a switching mentality from most jobs and most kind of design processes to go be an entrepreneur and say i'm just gonna get it out there and see what happens

Elizabeth: yeah i totally agree and it's that um especially when you're designing new products there's always this tendency to um focus on features rather than outcomes right um it's just kind of like what are we building what's the task flow what is this going to do when how is it going to dissolve result in that task in the end being completed but there's so much more to it because there's so many different ways to go about a feature or whatever it is an MVP and arrive at an outcome even if it doesn't have a great feature or you know even if it's not the perfect ideal vision of the product for you yet so i think that's so important as a north star when you're just starting your products when you're making your prototypes your MVP scan you have something that's so small that still results in some sort of a meaningful outcome even if it doesn't have all the features yet even if it doesn't have all the tech yet or whatever it is.

Andrew: so yeah no i mean this point is like we should just talk about this all night because it's the most important thing it's the hardest thing um it's all you know we or we could stop here and just say like just go do this right because it's it's it's easy enough to talk about it it's extremely hard to do in practice because you do want to perfect your thing or at least take it a little bit further you will be scared to ship your thing but you know you know again the adage of like if you're not embarrassed by the first thing you ship or the thing you ship you're waiting too long it's super true it's very very true and sometimes you won't know why you're embarrassed but this is what i tell folks who come through day one um entrepreneurs who don't want to pitch their ideas i'm like the more embarrassed you are the least polished your ideas is literally indicative of the growth you're about to have like you are the one who's getting the most out of day one right the person who pitches a perfectly polished thing why are they here just go do it right but like to the extent that you are uncomfortable and don't like what you pitched and somebody tells you how to make it better that's in infinitely valuable like that's the stuff and so again nothing is one inside and that's why there's this whole movement to build in public that's why there's this you know not related but very related but like the whole creator economy just people putting their own stuff out there and you know micro entrepreneurship side projects both in public like these are all manifestations of people who have now the tools and the abilities to make stuff just not doing it for their companies for the perfect thing but just like i don't know being entrepreneurial.

Elizabeth: I want to dive into a lot more of that a little later on but tell me a little bit more about day one like who ideally is it for you you know like if you're coming into this and you've got it sorted out and you're confident about your pitch and then you're not maybe going to get as much out of it so who ideally is coming into the program

Andrew: yeah yeah it's uh so so day one is you know there's two core premises so day one is built for early stage entrepreneurs right meaning that idea of entrepreneur that just get it started right just just launch something the earliest stages right when it's forming as an idea when even you as an entrepreneur might not call yourself an entrepreneur you haven't even said it out loud yet right but you're exploring am i an entrepreneur what is the thing what is the problem that i'm solving all the way down to i have the thing i'm building it i'm launching the thing i'm selling it but i'm working through the problems so we define early stages anything pre product market fit which again is is an extremely nebulous line in the sands you know it when you feel it when when you've got something and it's working but there's plenty of folks in day one who have raised money who are you know they've passed that milestone but they still haven't nailed it right they plenty of folks who have products out there in market making thousands of dollars a month iterating but they still haven't nailed it right all the way back to people who are exploring so that early stage and the reason why you can actually have a lot of diversity in that stage well it looks diverse like i just said there's all these different um use cases perhaps right different different people who are coming into day one but they actually have the same problems right they actually need to do the very similar steps and have the same coaching guidance the same camaraderie and collaboration um the same support and shoulders to cry on right it's you know the same yeah so so you actually have a lot more in common to anybody in this early stage than anyone one step afterwards if you take half if you take the microwas step afterwards life looks very different and you need a different thing but if you're here um so it's all about the early stage and and it's uh i mean that's kind of the main thing right it's all about the early stage it's it's also for folks who really want to level up right so growth-minded people people who have um again kind of like me wanted to be entrepreneurial and sort of maybe inched their career along and are looking to take that jump um you can definitely keep your day job and join day one and work either on side projects or even work on on kind of uh academic projects like you want to try out entrepreneurship right but you want to keep your day job you want to see it that's very much a fit right but it's growth-minded people who know that learning in the 21st century and learning entrepreneurship is is really not done anywhere i'm not gonna say anywhere else because i'm not that much of a you know like there's places to like be entrepreneurial like yc is an okay thing i've heard about them they're good right um but teaching entrepreneurship is is a unique animal right it's highly it has to be learning by doing it has to be learning through association um and i do think it's sort of my pedigree as a professor into a consultant into what i did at human ventures which was a player and a coach that sort of the sum of all those pieces is what day one is right it's a little bit of teaching it's a little bit of consulting it's a little bit of player a little bit of coach and it's unique animal frankly um i've lived in this ecosystem not too too long but long enough to kind of know we're just picking and choosing some of the best of all the things oh the other thing i was going to mention that defines that really differentiates day one in terms of where we sit in the world is we're not a venture capital firm at all right so we're entrepreneurially focused we're innovation focused we're here to you know launch a million new entrepreneurs help people get into the game and accelerate them all the nouns and verbs that you see spread around venture capital but we're not a venture capitalist we don't have funds we're not investors we are connected to tons of investors we help you find those ones after you kind of as you go through day one and you're launching it but because of that we're here to serve you and we have a fee so we're like school in that sense back to a different model i'd say up until now ish right the keys of the of the innovation entrepreneurial world were held by investors and they would only give out the means of production the guidance and support if you were investable and investible was a very very very very narrow definition right and the creator economy is not generally investable because you're building small things you're building passion projects the first time founder is often not that investable because you're about you're going to make all the mistakes promise you right but most investors basically look at first-time founders and say let's let them make the mistakes once they'll probably come back and then we'll invest in them right right um so yeah there's a little bit of we're trying to unbundle venture capital as well right and so and so we're friends with venture capitalists but also in bundling them and trying to create a whole new launch pad stepping stone for entrepreneurs to then get somewhere and then decide do i need venture do i bootstrap do i do something else?

Elizabeth: that's awesome so designer app is bootstrapped and um you know wondering what kinds of ratios are you sort of seeing of people that are more focused on going down that path of vc versus bootstrapping versus?

Andrew: you know just yeah honestly i was just talking to someone today who came you know we used to work together at human ventures she's from the adventure world um she's building a really cool product consumer consumer software products that could easily become a venture-backed business and ask her do you want to go down this route and she had the right answer she's it's literally i don't know right and so the way i'm going to answer your question is that yes there i could probably tell you a little bit of a ratio but there's actually a phase and it's close to the day one phase where you really don't have to and shouldn't choose right now some people will choose and i'll be like i'm going to get money because i can get it and they're going to go right always going to be that but the but the idea of you being an entrepreneur and being like well i'm you know i don't have a ton of money so i can't fund myself i'm not you know from that background or have that you know privilege or luxury so i have to do venture right that is no longer the only way so it's so it's definitely not a bifurcation that happens at the beginning what we're trying to do is it's push the decision way down the road and it's better for everybody because the decision to bootstrap is a basically a decision to pick your growth trajectory pick who you want to work with and um yeah pick basically you don't people don't realize it sounds sexy to build a big business it will change your life in various crazy ways right people don't and if you're if you actually have that decision in front of you you really should think about it you really want to do that um most folks would rather go build a five to ten million dollar business and go we live on a beach that's me right let's go do that um that sounds really nice and the um yeah and so i think we are creating and i think people are it's not even worth creating we're playing and people are recognizing there's a new phase and you see this all the time actually you start to that's the thing you can you see people doing this so it's not that we're creating it it's that yeah more people have done it and blaze a trail and it's beginning to happen so even just today whatever today is january 27th countley everyone uses calendar knows of it raised money triple unicorn three billion dollar valuation they're like a decade old company and they've only raised money one other time they're essentially bootstrapped right and on their way to massive growth right so there's um we in our first cohort at day one we had the founder of bubble which is a no code platform come speak to us they also were bootstrapped for seven years before they raised money so yeah it's it's very much becoming a different equation of like a or b and very much a okay we're just gonna be this and then we're gonna decide on where we take our capital from and what our growth trajectory should become and i'm here for it

Elizabeth: I love Tope from Calendly we did a spotlight on him on our blog and his story is absolutely incredible too it's amazing so um you know when talking about like this learning by doing learning by building i think that's also so important because going through this whole process doing it it makes you really learn whether or not you're cut out for this because it's a whole thing it's a whole lifestyle and it is stress in a in a whole other way it really is you know and i'd love to ask you a little bit about that too what what's your personal experience of like starting this up how is it yeah because you're kind of like it's a meta thing you're like an entrepreneur becoming an entrepreneur teaching entrepreneurs about entrepreneurship.

Andrew: it's very yeah i've lived at all the layers it's super true and yeah even where i was at human ventures you know player coach right i was as close as you could be an entrepreneur i had a paycheck i had you know i i was going to move on to the next project after we shipped one of these businesses and i said sayonara to the entrepreneur and they got to go live that life so no i definitely never lived the the emotional and the the the the pieces of what happens when you're in that messy middle um like after that first honeymoon phase like man before it's working in after you've started and maybe you've like kind of set sail uh yeah it's been a ride it's been a real ride um especially just in this year you know it's i would say there's a little i'm not going to try to call it a silver lining that i've basically been working on on a remote business during a pandemic which required nothing else of me because i did nothing else but build a business for the last eight months um which i won't say is like a healthy or positive thing but um but it was just it's just the reality and so and so yeah very here's it's yeah it's a super up and down right the what some of the things i've learned or one thing that i know is super true that i advise folks to is when you're building a business when you're setting out to build a business the best place you can get to is something i might call like a sustainable path sustainable from primary first and foremost a financial standpoint right many ways to get there whether it's whether it's because you've saved whether it's because you have a spouse whether it's because you can consult on the side or you can build a business as a side hustle to a day job putting yourself on like a ticking time bomb that is like a short runway is just a recipe for failure you're gonna both lose your money and you're going to lose your business it's just it's almost certainly not going to work right and so having some almost infinite runway that says i could just do this right for again there's so many caveats it's never infinite obviously but um but it's also not just financial it's like mental right it's it's well-being right so that if you are working a job and trying to build and you're not sleeping that's not sustainable right and so it's it feels like threading a needle but the the thing that's changed in the last five to ten years that's made solving that equation a lot more doable is the fact that it's it's these things like no code tools and these platforms that you can reach your customers you don't have to have this massive team you don't have to have this massive lift to go build a product put it out there and see if somebody wants it right the thing that usually requires that like jump and that all in and that even that capital raise is it used to be just like this big chunk of time energy and effort and money to go even get started and now it's just like minuscule it's just so much easier and you can spread it out over time so yes you might be building a little slower you might not be you know all in and living that founder life but it's it's much more sustainable so i think that's just an amazing place to try to get to right and and a lot of folks in day one are early enough that we can talk about that um plenty of folks have have jumped or you know there's folks who have raised money there's plenty of folks in the middle it's never a perfect equation but yeah i mean i said all that to say like here's how you it because it's super hard so i've had a version of that right i've managed to maintain some sanity and you know my wife works and um you know we've made it work and that's like a blessing in every single way right yeah but it is tough it is its own thing and that's not i'm not even telling you the ups and the downs of like when a good day happens and a bad day happens right it's just like how do you even have like a baseline so that you can like absorb those shocks right without feeling like a bad day is literally gonna send you into bankruptcy and stuff so i don't know it's that's a metaphor um just about preparing for it ahead of time if at all possible yeah i mean.

Elizabeth: there's a great tweet that i came across on your uh twitter from one of your cohort members Lisa Cooley and she said about day one they've shown us how to optimize your dream and not sacrifice your energy time or happiness which no one talks about geez and i was really moved by that i was excited by it um because it's so important in what i do in our program we teach mindful design and interaction practices it's sort of a way to you know as a grounding element and a way to set your mind you know to help you focus and kind of cultivate empathy and kind of see the big picture more holistically of all those different experience levels that you're going to eventually be touching with your designs and everything that you are going to be doing if you do take this on to building it into a product that you take to market and you know it's kind of also about tuning that inwards to how are we caring for ourselves you know it goes kind of against that hustle harder mentality of silicon valley of where you've got people going through YC on these extremely tight headlines going through incubators and accelerators and then coming out with an idea that they've really not tested very much and then pivoting to something else right away and it's just you know how do you kind of encourage your cohorts to find that balance to sort of pursue these things yeah without sacrificing their energy and their their mental health their self-care all of that.

Andrew: that yeah i'd say one of the first things that i think the main the main thing that we're the main thing the main thing that we that we try to do is that we try to deliver everything and create an environment where people are connecting because so many of the like remedies for these ways that you're you know falling through the cracks or you know you're losing your energy it's just when you're when you're just struggling alone right and you don't have people to share the burdens you don't have people to commiserate with um and so and entrepreneurship is lonely and that was before the pandemic right um especially for folks who aren't just like uber networked and can just like hang out and start up bars or whatever right like the people who are kind of breaking in trying who don't know a ton of people whose networks are from their professional careers wherever they're coming from ultra lonely ultra lonely and so the first thing that we do to actually solve that is it's community right we're in you know that word is overused um but in this day and age of you know there's a reason why everyone's striving for it's because we got separated and you know we put a ton of intentionality in in creating real community for um allowing members to allow day one fellows to build relationships and get to know each other and collaborate together and create a culture where you don't might not know each other very well but you kind of know what you're you're already in a community because you're already here together so that's really the first thing and really just helping people sustain that right that covers over a lot of the challenges of you know the irreducible issues and challenges and stresses of building a business is having people around you and i mean everyone needs therapy everyone should have a coach right you meant to do that put therapy off to the side coaching is super exclusive right there are founder coaches out there i promise you i know what they cost they're like 500 bucks an hour right it's just it's ultra exclusive and at the very bottom of it all day one is just a value play day one is the easiest cheapest way for an entrepreneur to get not just friends but collaborators and mentors and coaches on a way that's like hyper useful but also just there right and it's uh yeah and and just basically prioritizing those types of interactions and connections and and existences is is kind of the first thing right so so we try to just like say that's how we do it um and the second is like that idea of like being sustainable right we're basically not telling anybody like go get funding in the next two months yeah we're basically telling people figure out how you can build forever in this current state right we're basically setting the like golden like outcome as a sustainable healthy way and as like a foundation and then let people deviate from there because people will want to go harder they will want to take risks and that's great right go for it um and uh and that's what this is all about so so yeah i mean it's setting up foundations like that setting up communities and i mean we have a workshop tomorrow um on mental health right and the mindset of like having you know prioritizing your health and your wellness as you build so week one and day one is mental health and building in public it's mindsets it's shipping and taking care of yourself so um so yeah it's uh yeah i mean i hope if nobody went and like built anything out of day one we've at least like helped people have good entrepreneurial habits and mindsets that that basically isn't yeah as toxic as that's is out there

Elizabeth: excellent that's really at the heart of everything we're doing at designerup and i love that that is a focal point a foundational place that you're starting from with day one because that is kind of the soil for everything that you're going to be doing so that's amazing and i heard that you mentioned before talking about how being broad is a likely way to fail when you're kind of exploring ideas and i talk a lot about that in the context of finding your niche as a designer um it's like the paradox of specificity right the more specific your goal the more opportunities you actually can create for yourself like narrowing your aperture actually expands your horizons so many designers are very worried in the early stages that if they specialize or if they niche down their audience or their services they're just going to be limiting their opportunities like to find work or to find users or to reach people and it seems counterintuitive but i know from startup wisdom like if you don't define your mba if you don't define your target audience you're not you're going to be speaking to everyone and thus no one you know and then also you're just you're not really going to have that energy and that momentum to pursue these ideas that take a lot out of you if you're not passionate about them if you don't have some connection to them you know if it's not integrated into you and it's that kind of thing like where you know design is really that extension of yourself everything that we do is an extension of ourselves especially when you're taking something on as big as starting a business and you know massively affecting other people's lives through your designs through your products and um you know i don't really think it's like a generalist versus a specialist debate really it's just kind of a matter of like starting someplace and seeing it through gaining some traction around your ideas and and around that experience of going through the process and seeing it through that's so important

Andrew: Yeah you're right it's not generalist versus specialist and i think i think about i don't think about it that a lot but that's like impression to me because i'm a generalist right and um to be fair day one as a business has lived through the struggle of like how how you know we are a lot of things to a lot of people right i talked about how diverse that early stage is right so i kind of speak to myself i um when i when i give this advice and i know it's hard to take right i know exactly that fear of like oh we're gonna only serve one customer right but um but the idea of it not being about generals versus specialists because it's not about your input it's not about the things you do along into into the thing it's about how narrow that aperture is that you put all your stuff and i don't know probably find a metaphor about like water you know like like if you actually if you are a lot of i mean you could either be like a a narrow hammer and you're super good at a thing or you could be a generalist but either way if you focus it into the thing it's it is more powerful such a very generic way to say it for all the reasons you just stated right if you aren't whether it's being a designer who's amazingly good at a thing again that's more about an input but when you're entrepreneurial it's about it's you know it comes down to the customer and it comes down to the to the to the outcome you're trying to create the mission you stand for the the the passion that you have um which again you can have passion for your input and that's fine a lot of people have that they love a craft right um but but yeah you won't find the people who also love what you're doing right here's where the principle comes into play here's where it's most most important or like where it starts to make sense eventually you can be a lot of things to a lot of people eventually you can create enough surface area that you can solve big problems in big ways and be a lot of things right eventually right when you're first starting out entrepreneurship you have every disadvantage you are nothing you are no product you have no brands you are you are going up even if you're going into like a green field there's no competition you're still nothing no one knows what you are right and so you have to as you build your thing as you build presents products brand whatever it might be continuing to narrow is the only way to find reactions right to be something that's enough for somebody right so they say like find a hundred people that love you versus any find one person that loves you and get their feedback then find five and then ten and a hundred and but again it's super hard to say that i'll tell you our first cohort was a pretty broad cohort right um our second core is broad in some ways but it's also a more singular profile and we're learning that over time it's not necessarily the best way to do it right the better way to do it would be to find the thing and then let people come to you right it is slower perhaps it is a little bit of like yeah refine yourself disciplined entrepreneurs know that um and yeah so it's a lot of pre it's i appreciate sometimes i don't do it but it's it's it's it's real wisdom um and it absolutely yeah it's tough it's tough one though i'm not gonna lie

Elizabeth: it reminds me of what Seth Godin says about tribes you know build your tribe and um even that if that's a small one that um that kind of early adopter that that advocacy that you can build around an idea or a product is so important and i think that that is a jumping off platform for you to to expand more later but focus focus is so important and you know that kind of brings me to the importance of story right i mean for the work that we do as designers it's so much about story and it starts with the designers themselves like first identifying what is their narrative what are these things that they're telling themselves the beliefs that they have um the limiting beliefs that they have a lot of times about their abilities and their worth in the industry and all of that stuff and and then systematically through learning by doing through experience through action reshaping those narratives into something that kind of really pushes them towards growth and towards their goals i don't think that always looks linear like they expect and entrepreneurs know this more than anyone like you said all of the ups and downs it's probably too many to recount in a day but i think when you understand your story it becomes a lot easier for you to navigate those because you know what's true you know what's true for you and it's just more of a homing beacon to magnetize others that have a similar story or a narrative or who can get on board with yours.

Andrew:  yep that's uh plays you know for for what you guys are doing over there yeah i mean i know so so it comes so what you made me think of because man so many good thoughts in there i think it's yeah stories are so important for meaning right of our own meaning for how we understand ourselves that's like anthropological but um the way the way the way we think about stories um actually i saw someone tweet this today i forget who i would love to attribute them um but he basically said this idea of building in public this little trend happening right now is basically content marketing for founders meaning when you are when you have nothing else when you're a founder who's just got ideas or even just like a founder who's like i'm gonna go build this like all you've done is put yourself in the arena all you've got is your story and to be fair your story includes what you're interested in or what you're passionate about or what impact you want to have in the world but you haven't affected anybody you haven't built anything or hired anybody or whatnot so your store is very unfull but you have your own you have your story up to date and you have your where you're going right and you can see yourself through that narrative and um and to be fair i think all almost all entrepreneurs could probably get into this like philosophically have a version of that if you don't i don't know if you're an entrepreneur right if you don't have a story that says like from where i'm coming from through me to an outcome that's different than it is today i'm doing something whether that's to just like make you richer or to sell a product or to make a big change in the world and so yeah in some ways all entrepreneurs have a story and what we do is we try to get that out of you right because that story is the first asset you have and it's you said it's the first bat signal that you can put out that will get people around you and again i'm not the first i'm not coining this term but it's absolutely critical for founders to build their audience build their community build their first team members whatever it might be right and um but it's a total mindset shift right there's a few people out there who are maybe like naturally self-promotional they're the class clowns they just whatever right like the extroverts extroverts um maybe that's more than that now in our world of twitter and tick tock but there's you know you don't have to be an introvert to not like feel comfortable doing that right it's the majority of us and um and it's not just gonna be cringy self-promotional it's to figure out how do you tell your stories right how do you tell them in a way that other people want to hear them that are aspirational um yeah i struggle with that too right i struggle with being focused i struggle with both what's our story and how to be telling it all the time but i'll tell you one thing that founders have going for them is as much as i tell founders to find a sustainable way to build is they feel like they've jumped off a cliff so they feel like they are pretty much committed committed and then it's like you'll do a lot when you're committed to something right you'll do a lot to sort of either see it stay alive or try to make the landing softer and so and so entrepreneurship because you've thrown your hat over the wall you've got to go get it right so you start to tell your story you start to know man if i'm going to get the sale i got to go do a techno charter or i got to go do a pitch competition or i got to do whatever right and so and so it pulls it out of you in a really good way that puts you in your com out of your comfort zone and you grow that's another benefit to learn by doing right there it pulls it out of you that's that's true yeah yeah we actually we're getting a bunch of fellows um telling us sort of behind the scenes that like this week they're super scared to build in public yeah but they know it's where they're i mean but i i can hear it in their voices we all know this is where they're going to grow right so yeah it's really fun so you know for everyone out there that kind of has these entrepreneurial dreams and goals what advice do you kind of have for them if they really want to get something off the ground and what are some kind of realistic expectations that they should have about this process of designing and building new products and getting yeah no designing businesses i mean that's that's the thing so what i say the first thing that i think most folks run into as they even like contemplate that idea like they're going to go build a business or be able to be an entrepreneur is they want to probably rightly so avoid picking the wrong thing right they want to try to make a good decision at the beginning that's what that's that's a that's a fallacy right um as much as as much as you should have an investor's mindset like yes you're about to invest your time the problem with sort of just doing your due diligence at the surface is all that it's kind of like all the answers are outside the building all the answers are in the work right all the answers are two months down the road so you might be staring at ideas a b and c and you're like man i don't know which one i want to try i will literally tell you i don't care which one you try just go do one the worst the worst case scenario and here's the thing it's really just two to three months right it's really it's not that so just change some mind frame mindsets it's actually just a few months it's not that long you can quit it after two to three months like just go find that next thing right be be iterative at a time scale that allows you to go deep enough worst case scenario if you have three ideas you just spent nine months but that's way better than just like dilly-dallying up here right you would you would you would go those same nine months and you wouldn't get anywhere i've seen it way too often right um life gets in the way and so so there is a commitment just like kind of again this is i don't this isn't in juxtaposition to everything i said i just like jump off the cliff it's a little more like mentally go into a thing right keep your day job be sustainable but go into it and say this is my thing name it call it a thing and work on it right so to be fair that's why we've designed day one to be this time-bound eight-month program because we there's a few other reasons to it but we basically just want to push people hard fast for a time period you know within all these other ways to stay sustainable that's the main thing that's the main thing the other thing is um to bring people around you right they'll be your other biggest they'll be your biggest determinant of success and so if you've got people you're contemplating with build with them also try it out have some exit options right yeah be super irritative with it but do it and do it together

Elizabeth: i love that and i hope my students are listening because they go through this every time they're at the starting ideation phase of the course and they they finally pick an idea and they're like no this isn't going to work i talk to like two users potential and i just want to change my idea so bad and every time they say that i kind of breathe a sigh of relief because i know they're in the right place i know that they're now starting to do the work and and i tell them you know what you know they might worry for a number of reasons like maybe this isn't going to be a great case study for their portfolio when they're going after ui ux jobs or whatever it is and i always tell them you know having a grand success having a grand failure it's it's kind of the same it's it will teach you so much and that's the point of this program and imagine the value that you can add to your case studies in your portfolio if you have a huge failure and you can explain why this product doesn't work why people don't want this why you know this isn't a good idea.

Andrew: no no it's so real it's so real the the best stories are where you actually get to the end of your self or your abilities right very few people get to say i pushed myself all the way and then and kind of got beat like i don't know for job interviews for everything those are the best stories and like i wish everyone had a little failure column i mean i got started by failing in Uganda for six months like i came home we did not succeed i didn't succeed my friend succeeded later um but i truly found the edge of myself and got to reflect and be like that's what it's like and i'm still here that's it and that sort of set the foundation for things yeah it's it's so true and i'm you know i think.

Elizabeth: Final question to kind of wrap things up is a personal question i like to ask my guest and it is what does balance look like to you?

Andrew: oh i don't have a good answer i i i'm my own version of like the typical entrepreneur who is kind of mono focused but i have to have an answer what is balance honestly for me balance is not frankly frankly not pushing myself past honestly not pushing myself too far in the sense that i love what i what i do so i just like like to do it i do it a lot right but when i'm like done and i need a break i kind of just do it you know i kind of give myself the permission to just like in some ways work as long as i want and then stop working as long as i want and to be fair oftentimes i work a lot my wife will tell you i work a lot so it's not like it's not about the like time on target it's just about the permission to say like yes you're not saving lives like just i was i read a tweet yesterday and someone was like i used to work at the gap and when things got crazy we used to tell ourselves we sell socks and jeans and i'm like yeah i sell information i sell virtual programs like whatever so so yeah just having permission to just like do a little bit of whatever you want is one why the heck are you an entrepreneur if you don't have that and if you don't have that along the way i mean yes you're gonna sacrifice now and maybe you'll have a nice payout later but like you're in control so set it up for yourself you know um i i credit a little bit of that to one of our mentors day one mentors John Saddington who kind of said it i think he said in some tweets and maybe in a chat we had of like man if you're an entrepreneur why aren't you giving yourself an agency to just do a little bit of what you want and if you don't want to do what you're doing why the heck are you doing it is like kind of the decision you get to make that right just do what you want in a fun sort of way in a way that does feel like work at times but i don't know there's a lot to impact don't take me the wrong way but you know what i mean

Elizabeth: i love it and i think it ties in our whole talk and it's about that may be one of the most important mindsets of becoming an entrepreneur it's giving yourself permission permission to tell your story to build and to fail to go after your dreams and to remember why you're doing it in this for in the first place you know to just be able to have that ability to do something create something yourself and to chuck it in the bin if you don't want to do it

Andrew: yeah and take a night off and have a glass of wine and just like watch reruns of friends or something like we all need it so just go do it that's why we do it right

Elizabeth: i love it this was an amazing talk

Andrew: this was really fun i knew it would be fun thank you so much for having me on um excited to see this go live

Elizabeth: awesome it was really enlightening and i'm grateful for your time and i know that our designers listening to this are really going to gain a lot from the insights so if you all are interested in learning more about day one and what's going on over there check them out at Thanks again Andrew.

Andrew:  thanks so much

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Elizabeth Alli, DesignerUp

  • Elizabeth Alli

    Elizabeth Alli

    Mindful designer and mentor helping to create meaningful products and experiences.

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    Elizabeth Alli
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