Derek Andersen, CEO at Bevy & StartupGrind

all right today I’m thrilled to welcome drik Anderson co-founder and CEO of Bevy

for over 15 years Derek has been a leader in building communities working with companies like Salesforce atlassian

and Google he also co-founded startup grind a Global Network spanning 600 chapters in 125 countries and previously

co-founded common red later acquired by income.com um in addition to all of his

professional success Derek is a family man he lives in Palo Alto with his wife and four kids so Derek it’s awesome to

be talking with you today I’m really excited to be here with you Scott me too

um well one one of the things that I wanted to bring up is the and you know I’ve I’ve been curious about when you

know you started building your business for many many years now I’ve been curious about it because I think the first time I met you was at a startup

event it was a startup grind um I was working as a young sales rep at Dy and we actually sponsored the event and 201

at time 2012 yeah and I didn’t know anything about startups and building I just knew how to you know sell a

software product so you’ve you’ve been doing this for a while so I’m excited to ask you some questions about you know building businesses your startup

experience so let’s let’s start off by talking about the grind um I love the name startup grind and I’d love to hear

about your your first startup experience was it cool I feel like uh building a

startup for a while was like really sexy instead of going to get an NBA people wanted to go build a startup so what was

your first one what was it like I was working for for Electronic Arts and I

started to get these ideas in my head and I felt like I was staying up late at night thinking about it I just feel like

I need to get it out and so for a while I would just go to Starbucks that was

like right across the street from EA and I’d go at 7:30 what what I realized I realized something kind of Twisted and

that is that you know when I worked 110% that’s kind of the only speed I

know and so when I worked 110% at EA I was in the top 2% of

employees but if I worked 70% or 80% I was like in the top

10% so I just took that extra 30 or 35% of my energy and I started putting it

towards my own stuff and eventually I quit 2009 and I started an an outdoor

advertising company uh of all things and it was not something I had any passion towards but one of my best friends he he

was in the industry and this was my you know my the guy I was going to start

something with and it was really his idea and I was I got behind it and uh I

ended up quitting doing that like two months later but it got me to quit my job so it was not a good idea I TR I

couldn’t beg somebody to buy our products like I tried so hard to sell it

no one not even one person would buy it and um but it got me to quit my job job

so it kind of serves its purpose uh just just to clarify Outdoor Advertising are we talking about like

Billboards is it like in the woods trucks trucks okay all right very cool

super cool um so so you’ve built a youve you’ve built a few of these startups now you know you’ve got common red Bevy

startup grind you you you worked on this outdoor outdoor did The Outdoor Advertising one have a name I’m not even

going to say it okay all right it’s so embarrassing so you know wife says it

and it and she makes fun of me um but yeah but that’s what they’re supposed to do I mean I’ll tell you it was the name

was out as in like Outdoor advertising and gawking at it it was so it’s so bad

wow okay all right we we’ll just keep moving early days turning red thinking

about it oh why why do you keep uh you know we we’ll we’ll go in a little bit more why

do I har the guilt about uh my advertising company is that you’re saying why do I

failure uh no I’m more I’m more Curious like to know um you know we’ll we’ll

talk about startup grind specifically and then Bevy in a little bit but like you you kind of it sounds like you

you come up with these ideas and you have to chase them like what what is it about that that you have to do that you

know causes you to quit your job I think a lot of people don’t do that so what is it for you that keeps keeps you know bringing these new ideas creating this

Chase what is it I don’t know where the ideas come from everybody has ideas uh

but you know sometimes you just I think you know a good idea sticks with you for

a while or at least something that you need to move on I mean lots of things pass through your mind like oh I should do that and you don’t do anything about

it you see somebody else like launch that thing later and you’re like ah I should have done that but you know things that really start to stick with

you and they don’t go away over a long period of time um I had this experience recently where I was thinking about this

thing about a year ago and then pretty recently I I like woke up in the middle

of the night and I was like wide awake and I just had this like thought and it

was like I need to tell these people in my company about this idea and then it was like so random and weird but you

know it’s something I’ve been thinking about a long time and you know that kind of is push compelling me to move on that

thing you know so I don’t know you know for me like I thought about it for a long time I put

a lot of energy into it um and you know my son was being born at the time when I

end up quitting my job and that which seems like a crazy time to quit but in

hindsight but um it was like a deadline and I was like I’m quit I have to quit at this time like my son’s gonna

be born I’m gonna make sure he’s safe and okay and I can live without you know amazing corporate insurance and then I’m

leaving and um one once I got that I convinced my wife that that was

acceptable um you know it was like there’s no turning back that’s beautiful um so so like one

of the things that’s really cool about what you’ve done is uh you know building startup grind which it almost like

creates this community and fosters this environment where people like you who have decided to quit their jobs and get

started can kind of come together so there’s 600 chapters it’s helped 200 uh excuse me 2 million entrepreneurs I’ve

I’ve been a part of that Community for a long time I’ve learned about you know entrepreneurship and I’ve met tons of

people through it um and you’ve you’ve gotten to not only lead and then build that but you’ve also talked to all these

incredible entrepreneurs and and like brought them together learned their experiences um I I’d love to know a

little bit about you know if if you can have you been able to distill some of the things that either the best

entrepreneurs or at least most entrepreneurs need to have to succeed seed um or is it pretty different for

each of them I mean there are definitely some key patterns with every with

everyone that’s successful but the beautiful thing about entrepreneur and Entrepreneurship and also the tricky

thing is there is no one path so anybody that says like they if you do this like you’ll be successful as as an

entrepreneur in in a startup is is is lying um because you know there’s so

many other factors that are you know totally out of your execution control um

so look I think the biggest the most impactful thing for me that you hear a lot of really successful people talk

about is just customer feedback like what is what do the customers say I think for a long time I thought my ideas

were really awesome and then once once those kind of fall in their face enough

you start to finally get humble and then you you realize actually the only thing that matters is what customers think and

not only customers but customers that will pay so it’s very different to have somebody give you feedback like your

friend or your called roommate or your your sister and them to tell you they think it’s so great what you’re doing

it’s so different to then go to like an actual customer and then to look them in the eyes and even for them to say hey

this is cool I like it and then for for you to say well how much will you pay and then they say oh I think I pay you

know 20 bucks a month like okay write me a check and as soon as it’s this this is like Steve blank

you know Lean Startup four steps The Epiphany kind of methodology product Market fit you uh you know you look them

then you that’s when you get real feedback you look them in the eyes you don’t don’t even worry about the money just like it’s what they say next and

you just you know that comes with a lot of I think experience of making mistakes

and not doing it and um and then you realize like the only thing that matters is what your customers say everything

else is it’s kind of kind of a waste of time yep that that absolutely makes makes sense I I was talking with a

startup founder recently who he presented his idea to me and I said oh it seems great and he was like cool can I sign you up today and I was like

oh he got me uh it was pretty interesting um so

with I said no in the nicest possible way and then I gave reasons why rather than just run away and be afraid you

know to sort of engage with and did he did he try to rec did he like try to reposition it different cost different

yeah yeah we we ultimately went through a couple different steps there but um still said no still said no yeah okay I

mean that’s super helpful actually right so yeah that’s right um with uh with startup grind was this another you know

you were building let’s like were you building your outdoor advertising company while also building startup grind or like what was the timing like

for that and why did you ultimately do startup grind I I I like I couldn’t sell any ads so that and then I had somebody

come to me say hey I want to pay you to be a consultant I was like no I’m focused on my startup can’t I got 100%

you know I’ve read ink magazine I know I know what to do he’s like well just like how about like 20 hours a week so I

started doing that and then that became like I quit the other thing I started doing some Consulting for people just

basically doing my job at EA but with other people other brands and then um still trying to build my own products

and and then yeah friend and I talked about it it was like Hey like I’d been to a bunch of events they weren’t they

weren’t good you know they were low quality um there wasn’t a feeling in the audience that the people in the audience

had had real value to to give that really frusterated me because I felt like I I had something to give people

even though I hadn’t didn’t have a startup career yet and so we started hosting this basically like a salon or a

forum it with just a few friends and just like brainstorming and then it was good enough the first time that we we

did it again and again and startup grind was just this like hashtag I would use in some tweets to just like describe

what it felt like as an entrepreneur and um I I love that you love it I think people that are

Builders and that are in it they get it and they do love it and then people that are not a lot of times they don’t get it

they’re like oh that sounds that sounds bad it’s like no like listen to athletes listen to high performers like they’ll

talk to you about like grinding through stuff it’s not a negative it’s a positive actually it just means working

hard and like being creative and setting your own routine and just going for it and um so like it it turned into one

event and a few events and then I was building another product this common room thing and or common red common room

that’s somebody else’s product and um this guy I was I’m speaking with the mentor and he’s like hey like you know

this product you’re building it’s like okay but it’s not great but like the starbrand thing seems to have all like a

lot of organic energy and momentum why don’t you just like how much time you spent on that I was like I don’t know

like 5% he’s like why don’t you increase that to 10 or 20 and see what happens and so that’s that’s what we did and

then it like it kind of like took off and you know it’s where like if you have

a good idea it should have unnatural organic momentum because it’s so hard and what I

found I’ve never I’ve always worked the same amount of time and energy on everything I’ve ever done and just some

things like the ball rolled downhill and others like we just you know endlessly tried to push the ball uphill and you

and it doesn’t work and so um so yeah so you know star grind kind of went from

there and it started people started tending saying hey can I do this to my city and so we had chapters popping up

all over the world and you know one thing led to another and you know few years of really hard work and we kind of

we had this community of like-minded like similar valued people uh who the

values are give more than you take help others and make friends and um you know

we kind of started Gathering those kind of people around the world and it’s it’s you know kept kept the momentum ever

since do do you find um you know when when you talk to folks who go to your your events wherever they are do they

have this sense of like a community do they go to sell you know like for

example when I was when I when I went to your events it was like I’m going to find some Founders to sell to um but you

know you were sponsored though I mean you were like you know you probably kept it alive at that point yeah yeah might

have yeah um but but also I think like when I go to your events one of the things that is is especially cool is

like like I’m I’m always I don’t know really impressed with the quality of the the speakers that you talk to when you

interview and I have to admit like even you know I mentioned this when we were talking at the beginning but um right

before we started recording but I was like a little nervous because you’ve talked to everybody and um you’re you’re

like an expert now I would I would call you an expert at you know preparing for these interviews and having great

conversations and pulling great answers to those questions out like have you figured out a a technique or or like an

approach is it a huge amount of preparation is it just kind of like moving like water after they answer like

what what are you doing if I’m doing it right it is a huge amount of preparation and huge amount of work and uh I would

say I I probably cut some Corners these days more than I used to uh when I’m doing interviews I did one this morning

with um someone and yeah I probably cut a few Corners uh to do it but uh look

like I just try to I try to do what I think’s

interesting and and like I’m trying to learn so I just assume like the the

things that I want to learn and know are probably 80% 70% what everyone else

wants to know and learn and maybe there’s some stuff I have to you know unique Insight on and and that draws

something out um but uh yeah I mean it it honestly

like the interviews I’ve probably done 100 sort of VC founder interviews over the years it’s it’s it’s I’m generally

pretty selfish it’s like it’s sort of about me it’s sort of about me getting the insights I need and um on the

journey that I’m on and that’s where even even still like I did an interview

for Star crry this week with um an angel investor uh that’s one of the top

investors in the world I’m not raising Angel funding um but I learned so much

just sitting with them from an hour and you know and startup grind and I say

this to people who want to do chapters in their cities it’s like there’s no better way to network there’s no better

way to get to know important people have an excuse to talk to somebody who’s really successful and build build a

relationship with them because you’re not really you’re like hey I’ll get a room with 50 or 100 people to see you speak almost anybody universally will

agree to do it if you can get a 100 people in a room there’s this weird thing I I’ve read people have written

about it like almost anyone in the world will like drop everything if you get a

crowd to listen to them and it doesn’t have to be a big crowd like 100 people’s not a big crowd like you’d think it was

like a thousand people but like it’s not and so if you ask and do it in the right way and you know then you can get almost

anybody to come speak and then selfishly like I get to meet somebody that would never take a meeting with me it’s essentially like a a meeting with me for

me in front of a hundred people and like and usually the feedback

is good like oh these were good questions like well cool that’s like that’s what I wanted to know so you know

um but uh yeah I think if you just be authentic and real then you know people

can see it yeah I definitely resonate with that I think that’s the thing that when I

watch you talking to one of the you know the people that you’re interviewing it does feel like me a lot Scott that’s a

fair amount yeah I think I try to watch as as often as much as possible

but you know like you know you’re doing you look good you’re asking right questions I can’t rewatch any of my

interviews so do you do you hate how you look or how you talk more I just can’t I don’t know I I can’t I can’t do any of

it I can’t do any of it so I have to get everything I get out of it in the moment and then you know sometimes I’ll watch a

clip of somebody or a funny interaction or something but you know other than that I can’t I can’t watch any of it

that’s probably be good otherwise it would be like a little bit concerning you know like yeah that’s fair that’s

totally okay so like you you built startup grind and you you have these chapters entrepreneurs you’ve got

product Market fit there it’s growing organically and then from what I understand of of Bevy you you built this

really cool Community product basically like an entire business to help you manage startup grind and then you

commercialized it you you you made it available to other companies is that right is that kind of the the origin yeah okay and what what’s that like to I

mean are you able to then use these events to go out and say like hey um

we’re going to you know do an event and maybe you should consider it like while you’re talking to I don’t know some of these investor entrepreneurs or smart

folks that you’re talking to does it become like a natural next step to introduce them to Bevy or or not really

I mean I probably our like customer acquisition is not through startup grind

events it’s it’s really an because we built it for startup grind when it was

100 200 chapters we were already at some level of scale we didn’t build it as like a you know freemium Tri build a

community and they go and and maybe you know maybe that made it harder for us but it enabled us like our one of our

first customers was alassian and so and one of our first 10 customers was Salesforce so it really

was like a Enterprise sales sort of game and um you know those people aren’t

really attending startup grind but um but the events do I mean these are

public uh programs and events so like if you go and look at Google’s Google developer groups Community it’s all

running on bie you’ll see that it’s you know be’s there and that you know does create really powerful awareness I was

talking to one of Google’s competitors today and like they see it and they’re like oh we want what they have and you

know I mean I’m not going to tell them anything proprietary but they can see what’s public and you know and and so I

think like having a a sort of you know versus like an infrastructure tool is hidden in the back end of you know of

the of this the tech stack somewhere it’s like so it’s a little bit I think that that that makes it a little bit

easier to S sell and and promote and um and get people to sort of have a

conversation with you about it and are you like one of these crazy CEOs like Elon and Jack dorsy who run and manage

two different companies at the same time I am I am a very for mans

Jacky it’s cool to be in that category though the comparison but um I do run

both star grain and Bevy uh star gra is a pretty small company it’s bootstrap 10

people super proud of it actually made payroll for 13 years um maybe more proud

of that than raising funding for a venture back business because I think it’s much harder to bootstrap than than

it is to raise money and spend someone else’s money um but uh and and Bev’s you

know it’s not a huge company either it’s about 50 people um and we’re just trying to solve customer problems and luckily

the two things like you know like you know Elon and rock rockets and satellites like they’re connected it’s

the same you know evance and Comm exactly the same right but you know star grin’s one of bevy’s biggest customers

by usage and it’s one of the you know most active communities in the world so the fact that like I’m hearing about

those problems and experienc that every day keeps me sort of grounded in what software I need and I an hour ago was

with the product team they mentioned an issue somebody had and I was like I had literally the same issue this week like

10 times and I’ve been waiting to tell you about it I didn’t want to write it up so it’s going to be a big pain so

here we are let me tell you why I’m frustrated by this too and you know it

it um it’s good it keeps I don’t know the product people love that but you know I’m I’m a I’m a hardcore user of

the product so you know also head of the product so it uh those two things I

think and create a better end result I I really love when I get a feature that

I’ve wanted for a while that like you know the the amount of feature requests or whatever doesn’t quite justify it

yeah and then I’m and then I’m kind of like hey oh that’s what I wanted and you know I gotta stay quiet though yeah yeah

exactly so um were you guys at start of crime were you like one of the I don’t know it almost sounds like one of the first companies who would have had a big

remote you know I me I mean not one of the first but like you were certainly managing a remote team

basically building and leading that like did you have to travel a lot did you you know was it like a big Zoom kind of

thing like you know were you like gitlab and all these other companies building remotely yeah we’ve been remote because

my co-founder was in Portugal and now he’s in Canada and I have another co-founder with bevie in Seattle so we

kind of always had to figure it out since like 2012 or maybe I met my

co-founder 2009 so I mean I guess we’ve been working we just had to do that a necessity because we couldn’t he

couldn’t get a Visa at the states he would have happily moved here but uh you know that’s just how it worked for us um

and then we we did have small offices uh here right before the pandemic and then

but most company was remote so it’s really hard I think working remotely is not for everyone I mean again I’ve been

doing it 12 years maybe longer than that 14 years uh it’s it’s it’s hard so I I

think um you know I know it’s it’s probably a challenge for some people you have to after you’ve been home a lot you

have to kind of rearrange your life to then go be back in the office all day long or maybe you have to move in some cases saw Amazon this week saying

everyone’s gonna have to be back in the office by January um it’s clearly better

uh productivity wise I mean I’d be the first to say that but if you get people you know there’s a way to economically

make it make sense uh if you’re getting people at maybe you’re getting 70%

productivity maybe because of the different markets people in you’re paying at 50% uh Silicon Valley rate so

you end up getting some gains for sort of what you’re paying for but yeah we do have to meet in person we get way more

done in person than we ever do virtually uh and you have to have really mature thoughtful people uh that you know don’t

need to be Babys sa by anyone basically everyone’s their own boss and uh you know everyone’s you know responsible to

ship things and uh you know just it’s too hard to it’s it’s it’s too hard to keep track of what

everyone’s doing all day long unless they’re you know selfmotivated yep yep I I’m a Believer in exactly what

you described uh one one thing that um I talked with the president of one password earlier this week and one thing that he mentioned was that uh the money

that they save in offices and you know normal travel or office whatever they Ed

to just meet up with their team so it it almost ends up balancing out which I thought was pretty interesting that is interesting um one thing I was going to

ask you about you know you mentioned earlier you have sort of like an approach to work which is you put all your energy into it no matter what um so

I heard this great talk by Scott O’Neal Who was a Madison Square Garden president for a while CEO he basically

talked about how like work in life is like a teetered hotter seesaw where you’re always out of balance you’re

never managing and balancing work and life you know beautifully and elegantly um you seem like you know you’ve

mentioned it yourself too but like H how do you figure out the right amount of time to put into stuff like you’ve got a

family you’ve got four kids is it just all right I’m going to be there for the schedule and then I’m going to go back to work and I’m going to coach baseball

and then I’m going to play golf and you know how do you make it all work uh or how do you attempt to to try to make it

work the only way I can make my professional personal life work is because I’m a hardcore user of Ze that’s

uh that’s the only reason any of this makes any sense I I require everyone I

know and my team all to use the product uh we’ve been a a longtime user many

years and it’s it’s simply because of that tool that I’m able to keep track of

everything I don’t have to write everything out I can take videos I did it today of a of some issue I could just

send the video it’s right on my desktop it’s so easy that’s how I do it Scott oh

I love it I think we can just wrap up the podcast right now thank you um well I I do also we should talk

about site because all of those things are true it is an amazing product and uh

and we are huge fans of it and I I’ve used so many tools like it over the

years and nothing really ever came close to doing what you all are doing so thank

you for building such a great product Oh thanks man um well I I think building

something that people love is incredibly hard and I never feel like it’s you know

probably like you there’s so much left to do um one of the um one of the

questions I wanted to ask you about was was AI specifically um in startup grind

Bevy uh I’ve talked to a lot of different CEOs um whether it’s public

market CEOs everyone’s sort of like talking about um how amazing it is and it’s revolutionizing everything I get

excited using it personally in a lot of different ways um I I would love to know like for you guys um have you seen an

impact yet are you thinking about ways to use it or since it’s such a personal

personal B you know sort of personal product where people actually like meet up it’s less impactful for you because

there’s that Community element I think the thing that kind of woke me up

is seeing some of the smartest people in technology really speak about it with

almost reverence to the impact that it’s going to have when you see people like Reed Hoffman founder of LinkedIn or or

Sam Alman or Mark Andre um vode kosla who was a seed investor in

open AI in like 2018 um I mean just to see them the way they

talk about the shift that’s coming uh Sai Nadella like all these people um to see

that the Google co-founders get back into coding for like the first time in like 10 years 15 years they’re like you

know they’re like notoriously not even in the office ever like they’re just in Fiji like wind surfing allegedly uh uh

I’m just that’s what I’ve read you know firstand I was never invited uh but like

to see like the shift like I think that’s what really woke me up and you know and then and then basically we’re

like okay like we have this problem that we solve what are real ways that we can

make the problems disappear faster and cheaper and and so we’ve started Building

Solutions around that at anything from helping you create a an online

discussion really quickly with prompting you based off of the things that we see you’re doing of like things that may be

interesting discussions helping you create events really easily I’ve been bu I’ve been hosting events for 15 years

and it comes up with suggestions that like I’m like wow I like kind of laugh sometimes like wow that’s such a cool idea I should just it’s so easy I should

do that sometimes you just need a little bit of spark to like get things going and the AI at least for Community

managers I think’s really good at that the other thing is around content we’re

creating so much content these these interviews that you’re doing or the webinars that site hosts that are really

good that I’ve attended or the The Help Center or the like there’s all this content like how do we surface that in a

really interesting smart way that gets me to the answer that I that I’m looking for as quickly as possible that’s all

that’s all Community content Community created content or or um you know it’s

for the community so uh these this is sort of tip of the iceberg but I think

you know we as business owners and it can be I mean that as like if you own a group or if you have any responsibility

at all like you need to be thinking about how you can maximize your team’s time uh and energy to and using AI to

support what you’re doing and if you’re not then you’re behind uh you’re not like the boat hasn’t left completely but

like this things are moving so fast like I used I used chat gbt like five times

today for five different things um like how that’s a minimum thing that you can

do as you know and are Engineers using it to to code better are um you know are

you just are you using it to find better deals to negotiate better like I don’t know there’s so many things you can use

it for like you need to you know thoughtfully think through what some of the best applications are for your users

and then for yourself to be more productive um I I totally agree I think it it doesn’t

feel like it’s quite left yet but I I know for example um I read this quote recently I think it was uh Larry at

Google he basically said he’s willing to burn down the business or or bankrupt I think he said sorry I think he said

bankrupt the business in the pursuit of building a digital God and I and I

thought whoa if this guy is saying that like I gotta make sure I’m really focused

there yeah and and the actions reflect it right and yeah I mean you know some

of these things like it feels like some of these Trends they’re money grabs they’re they’re quick you know it’s like

I remember in 20ish I want to say 2012 like everybody

had a Groupon startup everybody yeah um and if and then like two years later

like everybody had a um an Uber

clone and so you know and then for a while was crypto and web 3 and like the

interesting thing about that is like many many many of the highest quality people in Tech didn’t get in in that at

all so I I don’t know I’m not like I’m not a complete hater on

crypto and Tech and web 3 like I’m not an expert but I think that gave me a lot of pause and now you see a lot of uh a

lot of tech people jumping in full board into this like really the highest tier

of people like that’s I don’t know that’s saying something to me yeah absolutely you know just and I think

just to wrap up on that comment if you look at who was willing to put not only money in like investors but then pay for

the product obviously there are some standout web 3 crypto products but like AI is where the money is going

absolutely and yeah and to some degree like and crypto is having a great Renaissance right now and actually like

I I’m pretty bullish on where it’s going to be but there’s so many strands of it that like just such a huge waste of time

and people grifting and AI I’m sure there is the same there’s definitely opportunist in AI but it feels like it’s

a much more solid part of every product moving forward so if you haven’t started start today beautiful well Derek it’s

been awesome talking with you and and thanks for everything you’ve done for both startup grind and Bevy and the

Outdoor Advertising business thanks for building a great product we love that all right man oh thanks so much see you

man