guidance counselor 2.0 · episode 271
entrepreneurship and startup life w/sheena allen
key takeaways
- design and spec out your ideas thoroughly before hiring developers to avoid miscommunication and wasted money.
- learn enough tech to avoid getting burned by developers, even if you're not technical yourself.
- being creative and having a different perspective is an advantage in entrepreneurship, not a weakness.
- give yourself grace, don't compare your journey to social media, and focus on doing what you love over chasing money.
- protect your time and mental health by taking breaks, staying connected to family, and being intentional about how you spend your hours.
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about this episode
learn how a creative founder from rural mississippi built a fintech company without being technical, from her first app to leading capway today.
I am joined today by Founder/Entrepreneur, Sheena Allen! We are going to dive into her story from being a creative in college to starting her own tech company without being technical! We also dive into tips for folks wanting to become an entrepreneur!
Come hang with us! Like what you hear? Connect with me - Website: solo.to/tdesseyn LinkedIn: Taylor Desseyn Tweet me: @tdesseyn Pics of the life, wife, daughter & dog: @tdesseyn
full transcript
auto-generated from the audio, so expect a few typos. the audio is the source of truth.
all righty good morning everybody hello hello happy hump day tell you what we need to bring back the camel bring back the camel I don't know why they ever took it away we need to bring back the camel um but uh for those of you who are tuning in here in the next few minutes welcome um I just got notified that we just officially hit the airwaves on YouTube and Linkedin so we'll get the people to tune in here but um as you are tuning in welcome uh guidance counselor 2.0 uh just let y'all know what this is this is um it was it is
a podcast it is a show but it's kind of more than that um it's a networking platform I've had a lot of people on this show um find Mentor mentees I've had people find jobs on this show from other people um I've had other people find actually friends and a lot of my guests you know just be prepared uh some of my guests have said their inbox get blown up too so uh but the the only way that you can be found is if you comment right we're not in the metaverse yet we don't have goggles on based off the recent cut from meta the
metaverse may be further away than we think um and so uh for those of you who are tuned in comment engage say hey um even if you watch this in the future I would still comment there are a ton of people that like go back through and like message people on this so again it's a networking platform it's a podcast and also the reason why it's a live show is because I have wonderful amazing Minds like Sheena on the show and you can ask her questions and not get billed for it right so ask questions take advantage of havashina on the show we were chatting
backstage like I said I don't plan anything um and I'm just so excited for this conversation um She's Got an amazing amazing story um and then I want to give a shout out to that conference um as well as well as render so she's gonna be at render as well as me in in a month or so um but I do want to give a shout to my coffee sponsor um that conference um they actually have their own co ffee beans I'm literally drinking it right now I promise it's actually really good um I am a coffee snob um I would say and their beans
are great so check it out but also um check out the conference in July up in Wisconsin I will be there at one of the Keynotes I'm very blessed to be keynoting um that conference um want to give a shout out to people tuning in this morning Ricardo Alex Joe Yolanda Becky Mark Morgan it's so good to see y'all this morning um all right enough of me running my mouth it's good the people what they want who are you and what do you do and we'll go from there all right a fintech financial technology company we're based here in Atlanta the company in itself um
we focus on consumer and Enterprise and what we do is we have this ecosystem of products and services um and they all answer one question which is does it create Financial access and opportunities I love that I love that so we're going to talk today about sheena's story uh from college to where she's at now I I think her story is going to resonate with a lot of people um so Sheena if you want to kind of give uh just go ahead and get started so talk about where you went to school where you grew up um talk about maybe being artistic and and uh
and we'll go from there yeah so born and raised in Terry Mississippi so it's a little small country town right outside the capital city of Jackson and when I say country like I really mean country like it was like a pasture I mean no we have no stop lights we have I think it's like maybe a few stop signs um I grew up like it was like literally a pasture of like cows and horses like across from my house so like really really country uh my my running joke is that no matter I lived in four different cities and my country accent does not leave
me so it's like attached it's not good it's it's embedded and literally embedded it's there um but yeah born and raised in uh Central Mississippi a little small Country Town um I was your model student uh which is always interesting because I don't um but you know I was I was like your model student so I did everything from like Bandit Club National honest Society I play you know Varsity basketballs I was like all these things graduated with the uh a 4.2 GPA only to get to my senior Year to my parents like yeah I I told them I was like yeah I don't I
don't think college is for me um and I actually applied to like all the major schools purposely so like Duke and Stanford and um you know of course like Ole Miss LSG but I was like I got in and I was like you know what I want to go to college like I want to be an artist because I love art so I from middle school photography like drawing always drawing painting and my parents were actually very much open so like if you was going to my room when I was still in in grade school my bedroom walls was like airbrushed and there was drawings
and I was painting on my walls so I was like yeah I want to be an artist and my dad very Southern very traditional was like oh yeah so I did I went to college with the Southern Miss University of Southern Mississippi go Eagles um in Hattiesburg which is in Southern Mississippi and that was um a double major film and psychology I minored in marketing film allowed me to be creative um psychology part really came from not wanting to be a psychologist by the way I wanted to actually do psychology and marketing and mix it with creativity so um an example of that like I
want to be that person that decided that there should be no windows in the casino because it's technologically it's telling you that you don't know how long you've been Casino if you want to spend money or you know there's a reason that everything at the counter when you go to the grocery store is like under five bucks it's all psychological um so that's why I majored in Psychology so yeah that was that was my journey up through going to college so here's here's a question and we asked a few more people uh Morgan comes in this is the way th e way you say stop
signs makes me think that they were viewed more like yield signs That's Country Living yeah seriously um uh love to see it the world always needs more artists John it's great to see you um uh artist fun um if it's still a side hobby that's awesome um so I I want to kind of you know drive this home a little bit so if I'm watching this show I'm like Sheena so you're saying you're a founder talk about talk about just that journey of marketing psychology and college to you started your own company in college too so I want to talk about that but like I
always want to get in people's brains not not in a weird way but like like trying to just figure out like like why did you want to go into why did you want to you know start something like why not be a part of something why did you is it was that that creativity side of things yeah you know it was interesting like my my freshman year of college um I created this website it was called izone Central I know that I think about I think that was like the worst name ever but uh it was cool at the time and I was like I
can build something better than Facebook uh this was 2008 ish um I don't know why it was just like I was like I can like do the whole UI ux and I just make this amazing so UI UA for those who don't know a user interface use experience um yeah I never I never did anything with it so my senior year of college I go to Walmart have this random idea for an app because if anybody's ever like bought a live from Walmart or with like CBS you get these super long receipts it's just nuts yeah it's like ridiculous it's like a waste of paper
like poor trees and so I was like you know what I'm a senior my parents about to cut me off I mean even had already cut me off but it's like I gotta figure out how to keep up my money so I wouldn't be able to like just like either email text myself receipts but I just keep up with it like I'll take my picture in my phone and like automatically registering so I can know lik e how much money I've spent and have left yeah uh I guess a little bit before my time so I tried it I'm Gonna Be Rich by the way
I was gonna be rich like next month because I love it just just the absolute confidence I don't need college I'm going to drop out my senior year like all the billionaires the seat maker yeah I like 50 downloads didn't do well at all but I I was not technical as to how I actually got it done was I actually designed it out myself I did my whole flow chart in Microsoft Word so really the way you design apps now of course like you have sketch and yeah figma I actually use the text boxes in word and that's how I designed out my very first
app I know who the heck I was doing so clearly um and I took it and I was like well I didn't know the time was on the flow toward our inspection a spec sheet and so I was saying like screen one if you hit this button it's gonna go to screen three or screen two does this I actually did not know the proper way to do it it was just like a this is what maybe should happen uh what's my day and I said hey Dad um I want to get an app developed once again Southern conservative traditional and I was like I want
to get an app developed my dad was like what I was like I want to get an app developer I've already designed it out I just needed Microsoft Word I just need to hire a developer and so he was like so what does that mean it's like I need to borrow three thousand dollars I have found a developer on guru.com so of course now like upwork and all those are huge for Freelancers but 2011 2012 Guru was actually IRS it was a really well-known freelance website and so I found this developer I sent him my my designs my spec sheet and I was like I
want to get this developed and he gave me like he was like I'll do three thousand dollars and so it's my dad mind you I did not grow rich barely middle class I'm just being honest and I hate like the whole rag to reaching stories it's not everybody's story but I definitely grew a very beautiful country very much of parents who were like lower to moderate income so three thousand dollars was like a huge ask yeah it's huge and the only reason my dad actually gave me the money is because I had a refund check come again so I hopefully spit my refund check from
school on developing my very first app uh like I started totally totally non-technical but I did do the designing myself I did my flow chart my spec sheet the developer developed it once he got done I did my own q a and testing my own deployment and it was truly just like trial and error and that's awesome that's so so cool yeah John comes in with a great question and this is kind of what I want to kind of get across today how does being creative change your point of view on Outlook on how to solve problems and issues you you face yeah I think
people there are creative I think that the I kind of said it earlier it's like not want to be put into a box it's like I want to just throw like a whole bunch of different colors at the wall and see like what happens from there like I I love the knots you know being one-dimensional and it's probably something that I actually argue I have are kind of bump heads with my investors on because investors are very much like do one thing great Focus here and I'm just like okay that is great for some people but I think people who are creative we are very
much nothing about being one Dimensions right it's like we're going to bounce and we're going to figure it out and we're going to do something different so I think you know one thing I would tell people from my journey is entrepreneur I think being creative and also being from the south I think are my two biggest advantages uh because a lot of people who are crazy you think a lot a lot of the the tick um that we know they are coming from usually their coastal areas your New York your Boston's your New Yorks or they're coming from Founders who uh well a lot of
our families are actually immigrants which I think is I think it's a very overlooked uh a lot of our big battles of immigrants and or they went to your major Ivy League schools and I don't check mark any of those boxes so I'm I'm not the white male that went to the Ivy League school I'm not from the coastal areas like I'm from the south um and it's people in the South because of the Bible Belt because of so many different things you grow up really different than what I've you know even learned of people that I'm now friends with or associated with who grew
up outside the South um something between those two things it made my perspective and my point of view is an entrepreneur different that's awesome that's awesome talk about you know so talk about your journey um from you know obviously you developed that app 50 downloads right I mean obviously I mean like did you feel like a failure I mean that obviously you probably had to eat away at you a little bit right well I thought to be rich like the biggest thing was like dang like I thought I was going to be rich and it just did not happen so that was like probably the
same like so I was gonna be able to retire Mom and Dad next month nope just just the mindset just the ideas of grandeur just like just fizzled like that but like but like like were you like I'm not fit for this I'm not doing this again or are you just kind of like all right on to the next thing yeah I I have fallen in love with the process so to me there's something about the process of creating that I was hooked I mean absolutely hooked because it was like one of those things even though it was only 50 people it was like there
was an idea that was in my head that I put on paper that I put in This Global accessible app store and somebody loved it somebody downloaded somebody used it and it was like I just completely fell in love with that and I was like nope I'm gonna try it again yeah yeah John John asked another great question John coming out here two for two being non-technical what's the best ways th at technical people can communicate Tech so it's easier to understand so I guess based off your experiences when you deal with really techy folks how can those techie folks explain Tech better to non-tech
folks like you yeah so this I would say from both sides when I am talking to a developer I give them I'd probably put it feeling every hole possible like I don't want them ever to be like well maybe she wanted that and maybe she didn't like I tried to literally be like if you hit button create it takes you to screen four screen four like I literally leave like no holes nothing left to be possible like I have no clue if she wants this or do not want this um and then on the other side when I'm talking when my developers are talking to
me um mind you of course I've been around Tech now so I know more of the lingo you know someone else um but when my developers are talking to me it's more of a conversation that when they say something I will I will kind of say it back to them to make sure I understood it correctly and if I didn't then they'll come back say oh no I mean like X and so that's one way that it's very much very being very the communication is very open my side once again I try to leave no holes no questions left answer and then from them if
I don't understand so if I immediately say hey well does that mean this and I usually if I speak it back in more of a layman's terms to them they'll say oh no I meant this but one thing I will I will tell people who are not technical if you're working with technical Founders you're non-technical but you work on someone who is technical the thing that I have found that works really well is learn enough I don't consider myself technical now I can do a little coding now because of just years but I can see myself but I always recommend or suggest to Founders know
enough that you don't get burned so if you have a developer that comes to you and say oh it's going to take me you know six hours through the splash screen in this I OS app you should know that's BS it does not take six hours to do slash money so I always suggest is you no one you have to be technical to be in technology but if especially as a founder or a CEO know enough that you don't get burned yeah I love that um Alex had Alex had a lot here um but basically Alex thank you for this but in a nutshell he
says you know I love your story went from ideas to figuring out how to use resources to get the solution um a lot of times people have an idea and they find out they need X Y and Z it's nice to know how to start using tools you already have experience with yeah again um you know and I want to kind of dive into that a little bit more kind of get a little a little high level here what's what's your advice to people right who know they're creative right like you knew you were creative and you still you know had to do the college
thing and kind of figure this stuff out what would you encourage people who are sitting on the sidelines right now who maybe have a job who have this desire to like want to kind of start their own thing or who maybe you know are in college right now who feel stifle because they're creative they want to bounce around what's what's your advice to people who are the creatives who aren't who don't have that out but yeah you have 24 hours um I'm never going to tell someone if you are working a job and you're living page to paycheck too quick to go be creative today
because you got to eat you gotta have a roof over your head now if you you're someone who has a fallback plan it's like hey Mom and Dad can I move back in for six months to a year I want to try X great Do It um if you're not that person then you got to figure out how to utilize your the best 24 hours that you have um the thing that I tell people all the time is everything that you do in life comes at a price you have to determine if you're willing to pay the price for that so if you're creative and
you're really needing to be in school or you're nee ding this nine to five you know if it means that you work nine to five or you go to school for you know six hours a day that might mean that you can't go out with the friends this not this Friday night or it might be when you get off at five you take a a nap and then you're up from you know maybe seven to one like I mean you figure out something that's also healthy for your body um but if you want to feed that creativity you also have to understand that it comes
at a price it's up to you if you're willing to pay the price yeah I love that and and something that I talk a lot about too about the job search and a lot of my content is being intentional with your time I think people are wildly ineffective with their days um I know I know I've had to you know I find myself scrolling through Tick Tock and you know like what the hell Taylor get back to work let's be effective how have you um how have you managed your time do you have any tips and again I know we're kind of getting super high
level here but I think this is really applicable to folks um have you found a way to manage your time you manage your days um you know especially maybe when you were still in college and trying to do all this stuff like what did that look like how did you time block yada yada yeah I don't know if I'm not question about recommend it for everybody else I don't have a life but I you know I I'm gonna be super transparent here I am still trying to do work through work life balance um it's not easy it's not it's not easy to do but I
I will say for me one thing that I have I've started to do is I've tried to get better with sleep um talk about that I I definitely oh yeah I I'm a napper so I I don't I can't tell you even now which I'm I'm getting better with I don't know last time I've had like a solid eight hours of sleep I am literally travel to the doctor for this multiple times I don't know if it's what my body is set up or what but I can sleep for two hours and then I can be up and I'll sl eep for two hours or
three hours and I'm just up so I'm really it's not like I'm going to bed at like 10 and then sleeping for eight hours and getting up for seven hours I'm a napper and I've been that way for maybe since high school so I don't know if it's crazy I don't know if the makeup of my my body or what it is um but even I saw that out for the first investor so lexo hannian is an investor in cap way um for those who don't know who that is it's Serena Williams husband so when he was with initialized capital um Gary Tannen and Alex
o'hanian used to be initialized of course Gary is now CEO of Y combinator and and Alexis now has his own fun um but Alexis was the first investor that I had ever heard or said to me hustle culture is not the thing to do like you gotta host those entrepreneurs you're gonna mislead and you're gonna be having parties but take care of yourself like don't glorify glorifying Coastal culture is not the thing like you have to take care of you because it's a Founder if you are not taking care of you the business does not run so everybody was like yeah you know like don't
sleep like this is this he was like yeah there's been times you're not going to sleep there's many times you're not going to be able to go out but he was like I'm not going to glorify hustle culture you have to take care of you hmm uh time blocking how do you have any tips at all are you obviously maybe still trying to figure it out yourself I mean again I mean what what what are maybe some some good habits that you've developed that that you can share um I I go home to Mississippi I try to at least every eight weeks at least I'll
try I've tried to do more um and the reason why going home is so important and it's part of the time block for me where this literally fly home for 24 hours or 48 hours that is it's something different about the country like there's not a lot of you know you don't hear all the noise and it's not the city and it's like I can wake up but I see deer a nd I see rabbits and I see you know squirrels and it's you know my my parents house sits on you know two or three acres it has nothing to be a rich or not
like in the country everybody's house is something about two or three acres yeah so it's just very different from the Holston and bustle like work life so I do that that's one part what I block out to do um I do try to block out time to go somewhere by water I'm a Pisces so water I'm not big on those signs I don't know those signs but I hear you I hear you so go ahead go ahead the prices of water sign and water or becomes me so I try to find time to to go for water but outside of like mine it's more like
everyday time block um I actually scheduled time to eat the same I get so deep into it then it's like oh crap you're like oh it's one o'clock in the afternoon by the way I want to say hey to the May's on my Tick Tock it's great to see you girl um let me mean it I hope you're doing well in Brooklyn um she was a former guest of the show too but um uh yeah no I have scheduled lunch I have to yeah so those are like some like more the everyday blocks I do like I talk to my I'm trying to talk to
my parents too much my dad and my mom call I'm convinced that my dad my mom yes I'm convincing my dad has no clue what I do yeah that's fine um but he's also super supportive it's like my daughter like yes I I yeah mostly what I do I honestly think of somebody told my dad tell me what your daughter does or die it's like sorry Dad because he has no clue what I do but he's super he's like yes so he calls me out all the time I'm just like Dad I'm in a meeting or I might talk on the zoom or I'm doing
this it's like okay but then he keeps talking so I'm convinced that he thinks I stay on the computer all day and I don't have actually have a job yeah but I do take time to speak to my parents my my grandmother um so I those are things like daily I try to cut out even if it's five minutes just walking bad with exercise I'm horrible I wi ll sit for literally hours and hours and not move and so I my friends and my family and even my doctors got gotten on to me get up walk even if it's going outside and it's walking for
10 minutes 15 minutes so those type of things I start to block out for me I love that um yeah and and I've actually talked with a few Founders about this um you know and you know on the engineering side too and I've had to be mindful of it as well about like having breaks and like not frying your brain I just feel like we're all fried right I mean even creators right like like name on um I mean she obviously is is a incredible Creator on on Tick Tock and um you know we've we we talk all the time and I know I've seen
her talk about mental health and burnout but like I just feel like we as Society needs to need to chill a little bit and take a breath and and knowing that's okay like yesterday for me like I just stopped working my family was outside my daughter and my wife were outside it's like four o'clock I found myself a course on Tick Tock and I was just like you know I'm just gonna go I'm just gonna go outside and just like drop everything and go out there and I feel dialed in today now is that a coincidence I don't know but I just think people need
to be more aware about taking breaks yeah and I also do that when I when I am at home I'm around my niece and my nephews I try to be very conscious to yeah so I was at home this weekend and my nephew was like let's play basketball and I'm just like on my computer on my phone and he's like TT and I'm like you know what you're right you're right I'm wrong I close my computer I literally sit my phone face down on my computer leave it in my in the living room and we go outside play basketball and it was so refreshing so
I I'm trying to be more conscious of that too I love that um as we wrap up here in the last few minutes you know I've always wanna um uh you know I want to give the guests kind of last few words of of wisdom or thoughts is th ere anything else that you maybe want to talk about something maybe we haven't covered um just an encouraging word to entrepreneurs job Seekers hiring man just anybody yeah you know it's hard give yourself Grace and whatever it may be like yeah um that's number one number two please do not compare yourself to people on social media
um um apparently everybody on social media is rich and everybody and everybody takes these amazing vacations and have these jobs or paying six figures that is not the case uh I'm pretty sure my number's off somewhere but I think like 60 70 people in America makes less than like 60 000 a year or something like that oh yeah I've seen that too I think like the average is fifty thousand dollars the average salary is fifty thousand dollars so if yes job hopping in today's generation is very normal stays somewhere a year two years to get experience go somewhere else get get more money um and
that's okay that's I'm not saying that's that's not you shouldn't do that if you can find somewhere better but don't actually feel better or push yourself down because you feel like everybody else is that you Sees at a job making six figures yeah that's a lot social media is not like real so um that would be two and my last one um is something that I always try to leave every time I do a conversation which is um just always focus on proving yourself right versus trying to prove somebody else wrong in whatever position that you may be in um and I promise you to
make it'll make things much easier for you I love that straight to straight gems I love it it's so good um all right the last question I ask uh of the guest though um so this is now the last question um uh so we had guidance so the reason why this show is called guidance cops are 2.0 is because we had guidance counselors in middle school high school in kind of college those are more like just advisors um but really now as adults like we don't really have a guidance counselor right so that's what the s how is just like you know tips and tricks
and you know thoughts and all that what would be your biggest piece of career advice to your younger self oh oh that's a good one um biggest career advice to my younger and my younger self will give me today or I would give my younger self going to give your younger self yeah you can do both that's an interesting way too I think I would just I would probably tell my younger self do what I love and not necessarily do what one with my parents want me to do or Society wants me to do and won't Chase because chasing money will actually not does not
equate to happiness um I know I say that people were like yeah give me a million dollars I'd be happy and you say that and I promise I promise you I get it I understand I know people and carefully see people who financially underserved a lot so people are struggling I get it so yes giving somebody you know money will definitely help take away Financial stress um but having money especially if you're doing a job every single day the money does not equate to happiness I'm sure none of us want to though have a doctor who hates their job and they're only there for money
because that is not going to be well for him for any of us if we get sick so I would say do what you love money will come the money will come it might not necessarily be that you're making six figures but I Personnel teachers who make fifty thousand and they are really happy because they love love what they do yeah yeah I love that so much I think you know in full transparency I struggle with it right I mean you know I'm as a recruiter we're a sales organization right like they literally put out the score card of where you are at with everybody
else in the company every week right um I for my mental health I've stopped looking at that for the last three or four years now which has been good for my mental health um but i s but I still compare right there are people at vaco who make way more money than I do right and but they 're also but like my mission is to be very visible publicly to give back like and and I've had to be confident with that like you know and you know I took kind of you know I mean hell just if we're being vulnerable here I was talking about
my wife two days ago I was like did did I make the right career change right I was heads down I wasn't doing content or social media or brand building or Community Building anything and because I got tired right I was telling you off air like I was tired of being your typical recruiter and it's been tough the last two years I haven't made the money that I have before working with recruiter you know what I'm happier now I'm happier and I know peace of mind is priceless it really is it really really is so that's awesome Sheena thank you so much for hanging out
with me today I appreciate it um hopefully uh y'all enjoyed this conversation as well um Tick Tock it's great to see you all this this morning um Facebook LinkedIn YouTube and Twitter we're on all the platforms but Snapchat um go connect with sheen on LinkedIn um is there are you on Twitter what's about LinkedIn like if people want to follow up with you somewhere should they check out cap away where where where should people find you yes so Instagram Twitter my uh handle is who is Sheena um w-h-o-i-s-s-h-e-e-n-a LinkedIn he's probably just look up Sheena Allen I'm there uh Facebook I think I'm just backslash
I'm backslashing a D Allen and I do have a sweet potato and a tick tock but I only use it actually I don't use it it's on my phone if I'm just being honest um but I do have one if if you happen to see me there I it's not a well maybe a catfish page too I've had a few of those but yeah and are you guys find my personal website is sheenaallen.com definitely check out capway c-a-p-w-a-y check it out check it out awesome well y'all I hope you all enjoyed this Wednesday's episode of guidance counselor 2.0 tomorrow morning um unicorn finders because a
man can't have too many pod casts I'm live with Kent Dodds tomorrow so for those of you do not know Kent Dodds is very very prominent engineer um was on the react training team then was with remix um uh which was a JavaScript framework that recently got sold to Shopify um and then now he is doing his own thing called epic web dev um so really really excited to talk about that tomorrow with him um but again Sheena thank you so much for hanging out with us today we appreciate it I appreciate I know everybody has everybody's starting to make the comments um and y'all
have a great one we'll see