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Building a Successful Remote Startup with Andrew Hutton

Andrew Hutton is the founder and CEO of Day One, where he is building an ecosystem to power the next generation of entrepreneurship. It launched in summer 2020, and it has helped over 50 companies since then.

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Remote entrepreneur

Luis Magalhaes:

Welcome ladies and gentlemen to another episode of the DistantJob Podcast. I am your host Luis, and this is a podcast about building and leading awesome remote teams, or maybe in this case businesses even, because my guest is Andrew Hutton. Andrew is the founder and CEO of Day One, where he is building an ecosystem to power the next generation of entrepreneurship. It launched in summer 2020. You think that would be a tough year for building anything, yet Day One has helped its fellows found over 50 companies since then. Andrew, welcome to the show.

Andrew Hutton:

Luis, thank you so much for having me. I’m really excited to share how it’s been and dig into all things like you said, building teams, businesses, remote collaboration, it’s very much part and parcel of what we’re doing here.

Luis Magalhaes:

There are many places to start by, but first, I just gave you my introduction. Did I miss anything? Is there any blanks you’d like to fill? Anything you’d like to tell ourselves and our listenership about yourself and your career path? And maybe how it eventually intersected with remote?

Andrew Hutton:

Yeah, absolutely. You definitely got it right. Building Day One have been building since last summer. Like all startups, the ideas, the seed for Day One was brewing and definitely incepted in my brain from earlier. But actually the timeline of Day One very much corresponds with this most recent remote, the way a lot of the world has gone remote due to COVID. The ideas for Day One were brewing in the winter to spring of 2020, just as … At that time I was still at Human Ventures, which is a startup studio in New York City.

Andrew Hutton:

We were building businesses. I was beginning to think about what was next and how … The mission of Day One is what led me to build Day One to leave a place like Human Ventures, was the desire to really expand both my personal reach and just the reach of how could we … The how might we question that I had in my mind was, how might I, how might we support orders of magnitude of more entrepreneurs? How might we bring the things that entrepreneurs need to succeed and get it into the hands of more and more founders?

Andrew Hutton:

Very much leaning into the adage that talent is everywhere. Startups are everywhere, but the opportunity and frankly, the resources and the support and the ecosystem and the community is not. Actually from the very beginning, I’ve always wanted Day One to be remote, to be a virtual ecosystem because when I was launching it, the second before COVID hit and most of the world went virtual, everything was very much city focused. You have Techstars, one of the biggest accelerators in the world has these city-based programs.

Andrew Hutton:

People fly all over the country and all over the world to literally go to the cities where these programs live, and every city has their own tech hub, their own incubator. It really feels atomized and obviously there’s the bigger hubs. There’s the bigger centers for technology innovation for startups that again, people go to and gravitate to. Yeah, building Day One through the course of the pandemic and how the narrative has been around the unbundling of these hubs, of the locations and how we’re all deciding, is the world going to be remote?

Andrew Hutton:

Is it going to be hybrid? What’s happened now that startups have left the Bay area, have left New York City? We were trying to solve some of those same challenges from the very beginning. Yeah, the pieces of the story that I think are worth noting, I was building businesses at Human Ventures for about three years before taking my talents on the road to say, “How can we support hundreds and thousands, maybe hundreds of thousands of founders?” That’s Day One’s mission.

Andrew Hutton:

Along the way, we’ve learned a whole lot about building this remote ecosystem, supporting founders remotely, bringing people together to collaborate and yeah, excited to unpack those today.

Luis Magalhaes:

Yeah. Let’s get right to it. As someone who’s built a couple of businesses, I don’t even know if I can call them business, because they were mostly one man shows, right? There were mostly one man shows, but I have the experience of building a couple of businesses, where I was the founder and the singular employee. There’s this concept in writing that we writers call the resistance. It was popularized by the War of Art by Steven Pressfield. I don’t know if you’ve ever heard of the book. It’s quite popular.

Luis Magalhaes:

It’s basically about, when you’re trying to do creative work; you need to push really hard, because it feels like there’s an invisible force holding you back. I definitely feel like that about building a business. Now, that’s on my relatively small one-man businesses that I’ve built, I’m very lucky to say that they were all ROI positive, so that’s cool, but still I can’t imagine building a company, where you actually rely on other people to be to build a team. Just the thought of starting is almost paralyzing.

Luis Magalhaes:

This was in a time where you could meet people, you could be in the room with them, you could try to talk, figure things out together, et cetera, et cetera, et cetera. Now we don’t even have that right now. Now everything is handled remotely. I guess the first question would be what is the way to push against the resistance? What seems to be in your experience the most common ways in how to do it now online, over the internet?

Andrew Hutton:

I love that.

Luis Magalhaes:

If someone has an idea on a piece of paper, where do they go from there?

Andrew Hutton:

I love that. I’m going to co-op that concept, that idea of resistance, it totally gets the essence of a startup. You’re right, there’s in creative forces, in creative anything, writing, shipping that piece of business is very much similar. Man, there’s so much to unpack here. How do you get past that resistance? The first thing that I think about and some of the core foundations for Day One, but I’ll just even think more broadly. The core foundation of getting past that resistance for an entrepreneur, really does come from community.

Andrew Hutton:

It really does come from people. We’re now leading into like, to get past the resistance, you do need people. If you just take an analytical, not an analytical, but if you look at places where startups were formed, the fruitful centers, what typified them was the fact that there was a culture, a critical mass of people who are all bouncing around each other, who are all culturally of the same mindset that we’re sharing ideas, were helping each other out. Recreating that virtually is somewhat of the simple idea.

Andrew Hutton:

In practice, it gets a lot harder. I’d say that’s where the rubber meets the road. How do you create a virtual ecosystem that has the same characteristics of Silicon Valley or New York City, or even just like the smaller clusters of people in these ecosystems? Because they’re not monolithic, it’s not just Silicon Valley, right? There’s people. There’s all these different cliques and all these different networks even within these geographies. But geography didn’t matter. For a moment we unbundle geography.

Andrew Hutton:

Geography stopped mattering. We all stepped back and said like, “What’s happening?” Again, Day One was coming into existence in this moment. I’ll tell you the thesis that we picked up, one of the things that first breaks people out of the, well, that helps people form into those communities, into those togetherness and collaborate is the idea of a time-bound, cohort based program. Program almost doesn’t really matter as much as the idea of contained time period and a contained number of people, all sharing a similar desire, goal, even just a shared identity of I’m opting into this known thing.

Andrew Hutton:

The fellowship that is Day One very much draws on that power. We don’t ask people to be leaned in, in an indefinite way. We say there’s a time period. There was a baked eight weeks. In the future it will be 10 weeks. We say there’s a contained number of people. It’s not just meeting everybody. Everyone in this has been selected as a worth meeting and worth collaborating with. There’s going to be a smaller number of people who are a better fit for you than others, and so find them. But it’s about creating constraints and containing.

Andrew Hutton:

Every creative field has that same thing. It’s about creating the constraints and containing the energy and the work. When you give people those constraints and you say, “This is how we act. This is where we meet. This is when we meet.” It gives people the freedom to say, “Okay, it’s not infinite and unbundled, it’s all here.” I think that’s the first thing that needs to happen. You create those constraints. You create those time-bound structures, and in some ways you’re just going to start to let people go.

Andrew Hutton:

There’s obviously more to it than that. But that’s the very first thing that I think about, in terms of helping people get through that resistance in the virtual world.

Luis Magalhaes:

All right.

Andrew Hutton:

Yeah, jump in, jump in Luis.

Luis Magalhaes:

No, no, no, no. I want to get something out of the way, just because I don’t think it should be the first step. But I think that when you talk about building your business and specifically building a startup, the first thing that people think about is funding, right? That’s probably not the first step. I don’t think it would be a first step.

Andrew Hutton:

No, it’s not. Definitely not.

Luis Magalhaes:

But I do-

Andrew Hutton:

It’s definitely not.

Luis Magalhaes:

… think that it’s the elephant in the room, so we should probably get rid of that and then people can enjoy the rest of the show and the rest of the important facts.

Andrew Hutton:

Sure.

Luis Magalhaes:

Right? What is the stage that you think it usually makes sense for people based on what you’ve seen from your cohorts? What makes sense. What do they need to have on the table so to say when they go get funding? Part B is, it seems that selling an idea it is such an intimate thing that requires so much presence and so much emotion and so much dominance of the room. How can you convince people properly to fund you when all you have is a zoom call? Those are part A and part B, so timing wise, and then how do you pitch effectively online?

Andrew Hutton:

Yeah. I think actually the answer that I have brings those two thoughts together. Pitching for funding, my advice for startups is, you’re always taking into account units of progress that you’ve made. The first unit of progress is to have an idea, to have something. Really the first unit of progress is yourself and the sum of your experiences, the sum of your skills. Some people walk up to a founder and if they say, “I want to build a business,” they’ll get funded because they themselves are enough progress.

Andrew Hutton:

They’ve shown enough capability. That’s what they bring to the table. The first thing is you. The second thing is your idea, and an idea that starts us down a whole thread, because what defines an idea, how do you show an idea as good, is where the rubber hits the road. How do you go refine that idea? Who validates it? Are you talking to experts? Are you talking to customers?

Andrew Hutton:

Eventually you start to build. What I always suggest, well, really almost answer A by answering B is that, to fundraise in this remote world, you should be relying or it behooves you to rely a lot more on your evidence, your traction, because you don’t get to do reality distortion in a room.

Luis Magalhaes:

Exactly.

Andrew Hutton:

To be fair there is a frothy version of the funding market, where people want to just bet on big picture vision and believe, and they want you to bring your Steve Jobs and sell the future. But there’s a lot of other investments, and I would say the vast, vast majority of VC even VC investments at the early stage are built on some early proof points of traction around yourself. You’re a fit for this business and you can prove that, whether it’s your skillset, your unique passion, your connections, whatever it might be. Your idea is good and sound and you have the data points to prove it.

Andrew Hutton:

Whether it’s just a really well-reasoned idea with a business model behind it, it’s expert validation, it’s customer validation. Then down the road, you’ve built something, you’ve started to show that this thing is buildable, it’s working, whatever your prototypes and MVP start to be. I generally would suggest that folks get into market. They go from not just team, not just me, not just the dream, the idea, but they have products in market. If you can have customers, and that’s almost obvious advice. Go have a customer, go show that somebody wants your idea.

Andrew Hutton:

But in this virtual world, we are living in a moment where the proof has to be in the pudding. There’s less reality distortion. The dynamics are much more honest between you and me over zoom, and the data speaks for itself. Yeah, when I advise founders, it’s always to clear away the clutter and clear away the noise and say, “What are the proof points that you can stack up right now that are in your control?” When every founder is thinking about funding, they’re always getting down to this equation of how much can I do with my current resources?

Andrew Hutton:

What can I do with more resources, and what do I need to do to go get those more resources? They’re unpacking that equation, and so helping founders find more ways to do more things and show more progress, always makes that funding ask easier. It’s that much more important in our virtual world for certain.

Luis Magalhaes:

All right. The other alternative is of course, bootstrapping, right?

Andrew Hutton:

Right.

Luis Magalhaes:

There’s a thin balance there I feel, and it requires some, I would say nerves of steel in some sense that sure, you can bootstrap something with relatively small money, but then if want to create something big, usually you have to get a loan, let’s say for an amount-

Andrew Hutton:

Something, yeah.

Luis Magalhaes:

… that can potentially cripple you if things don’t go as you plan. Am I wrong here? Is this a situation where businesses, if they bootstrap and if they want to be comfortable in a place, where the founders then don’t feel like their personal livelihood is going to be threatened, that there’s a chance that they’ll never be able to make it big. Is this the way people look for investors in general? Or am I off the mark here?

Andrew Hutton:

You’re not so off the mark. I think there’s that, everything you’re saying is right. I think there’s a little more to it as well. I think there’s really two scenarios. One is, when you’re bootstrapping you’re … Well, here’s the thing. I think we’re in a world these days, the funding environments are changing. The ability for entrepreneurs to take ideas really far with little resources is never been so available. It’s never been so strong for a founder to use the available no-code tools to …

Andrew Hutton:

The technology stacks that founders have available to them, allow them to be so much more prolific in what they can build and deliver as themselves as, without funding that the idea of bootstrapping versus raising venture is actually something that it’s no longer this dividing line at the very beginning. It’s actually something that I would say is a decision farther down the road that most founders …Well, that has been the case up-to-date.

Andrew Hutton:

Meaning, there’s this whole new phase of things, where founders should be starting before they even actually asked that question. It’s agnostic to their funding question. This goes back to the question before, is just get building, just go from your idea to your customer, to your product and market, start building, get somewhere. There’s very, very few businesses that can’t get all the way to that level of at least an MBP in market without raising much more than, not even raising, without spending much more than a few thousand dollars.

Andrew Hutton:

Whether it’s on these SaaS tools, whether it’s to spend on ad platforms to get into market, whatever it might be. All that to say, the decision of bootstrap or VC actually happens later down the road these days, because you really should just go. You really should just build. The founders always then hit that moment that I described earlier, which is, can I keep building with my resources? Do I need more money? Do I have enough to raise? It’s the sort of, there’s a pivot or persevere moment around fundraising.

Andrew Hutton:

Do I need money? Should I go get money? How do I fundraise? Is it worth it for me to raise right now? Should I do more, et cetera. Answering that question is one of the big, first milestones that a founder runs into. I’m forgetting where the question started, but I think this is a really key point around, when do you choose to fundraise? How do you bootstrap? How do you not have money for it?

Luis Magalhaes:

It was a conversation starter more than a question, so please.

Andrew Hutton:

Yeah. It’s a big one for founders at all … Every founder runs into this moment right?

Luis Magalhaes:

Yeah.

Andrew Hutton:

That moment of do I raise money or do I not? Do I have enough money to keep going on this path is that key critical moment that every founder fits. One thing that I advise founders to get to that moment, to at least even make that decision a lot easier is, to always try to build from a place of sustainability. By that I mean, can you find a way to build so that your whole life can continue? Meaning, can it be a side project? Can you keep a day job and work on the side?

Andrew Hutton:

If it’s something that requires more than just your nights and weekends, maybe you can do a few freelance projects to pay the bills while you build this business. Maybe this business does start to create revenue and you can start to sustain yourself from it. Starting from that place of sustainability is just really advantageous, whether you’re going to go raise VC money down the road or not, because you can basically … You don’t have to ask permission from a VC to keep going. You get to decide, “I think I’m onto something.

Andrew Hutton:

I think I’m working on something important. My customers, my stakeholders are telling me this is valuable. I’m going to keep going.” The decision to raise VC is then just something that you get to ask yourself, “Do I want to take this to the moon and do I want to start to grow faster?” Versus, “Do I want to grow this in a slower, more sustainable way?” It’s actually closer to what kind of business do I want to build; versus is this an investible business? That’s just a really exciting place to be, because there’s an idea that just throwing about the idea of permissionless entrepreneurship.

Andrew Hutton:

You don’t have to ask a VC for money to go make the thing happen. You can basically just keep building. I think we’re in an era of permissionless entrepreneurship more so than really anytime before.

Luis Magalhaes:

Yeah. I want to expand just a little bit on this topic of money and bootstrapping and fundraising for a while, and then jump on to other components of the part. But I do remember a personal anecdote that I think it makes, an anecdote that I think it makes sense to bring up now. I had a friend who invested, who found a niche, identified the niche in the market and starting building something as you say, sustainably as a side project, et cetera. He did it over let’s say the course of six months, which is not a lot of time.

Luis Magalhaes:

He’s an IT person. He is an engineer, so he can code himself and then he got some money, invested some money in some colleagues to help him out, et cetera. The thing was going slowly but nicely shaping into a nice product. Only eventually someone identified the same niche and threw a couple of millions at it, and got to market first. That was very frustrating. Eventually the project did work. It did make some money, but in some cases there’s not a lot of … If you’re first to market, you dominate right? In many cases, I would say that’s one of the laws of marketing as far as I’m concerned. How should this factor in the equation when people are deciding how to fund?

Andrew Hutton:

Yeah. That’s a big one. I was going to say this to your previous question, I’ll say it now, deciding to fund is close … Like I said, I did say it before, “It’s closer to a decision.” I want this kind of business to happen. I want to create a scaled business. I want to shoot for major growth. Of course, then you have to convince somebody to fund you. You have to show that you have a scalable business. But the decision to do that is largely a decision on selling the outcome. It’s a decision on selling not just the team, the dream attraction, but it’s selling the possibility.

Andrew Hutton:

I think that comes back to your question of what happens, when somebody is also entering your space and maybe is selling that potential big vision, that big dream and is raising money. You have to decide, are you playing that game? Does it make sense to either go head to head with them, to try to get ahead of them? Maybe you can just imagine somebody taking your same business and scaling it, or again, it’s almost a decision on your end. Do you want to serve a small niche?

Andrew Hutton:

We’re just entering into this world, and it’s very much a function of the way we’re living remote lives, the way we’re living on the internet, we’re consuming content. It’s part of the creator or the passion economy. There are plenty of solo businesses, small businesses that will survive and exist around niches. The world is way bigger than we think, and the tools that the internet gives us to reach those small niches, if it’s truly a niche, will allow you to stay out of the lane of a bigger player while reaching plenty of folks to go make a business out of it.

Andrew Hutton:

Again, I don’t usually tell folks to play the competition game in the early stages of building a business. It’s too distracting to say, like, “What moves are they making? What moves am I going to make? How am I going to predict what they’re doing?” It’s impossible and it’s very distracting. I advise folks, play your game, play to your niche. If you’re truly solving a problem, you’ll create customers, fans. You’ll create something out of that niche. If you then decide to grow … Again, there is a moment where yeah, you should start to blitz scale, do that kind of thing.

Andrew Hutton:

But again, if you build a business in a niche … The example of your friend is, again, probably not uncommon. You build a business, someone builds around them, but it’s a little bit of two sides. If they’re actually building for a niche that’s small enough, that’s unique enough and they have the solution for them, I imagine part of the solution, part of their survival story, was they got extra close to their customer. They figured out how they were different from the big company, which is basically what I would advise founders to do from the start, be weird, be focused, be something unique for some small set of people.

Andrew Hutton:

Again, from there you’re either going to find certain, you either survive and thrive as a small business, or you’ll create a seed for something much bigger. But no one wins by fighting a big giant when you’re a small. Basically that’s a recipe for failure. You’ll spread yourself too thin. You’ll get stumped. You won’t stand out. You basically need to start small, where do you want to be big or stay small?

Luis Magalhaes:

Got it. Got it. Okay. Let’s shift gears a bit. By the way, regarding the niche and being a bigger world out there, I encourage listeners to look up A Thousand True Fans by Kevin Kelly. You can just Google it. I don’t know if you’re familiar with it, but it takes quite well on that concept. I think that would be recommended reading as far as I’m concerned. Now that we’ve got, the question that everyone wanted to hear about, out of the question that everyone already wants to ask, now that we’ve got that out of the way we can go on with the other important stuff.

Luis Magalhaes:

I would say even more important, which is now we’re all at home. This is a remote society as far as most work is concerned. Let’s say that someone has that idea on paper, someone has that idea on paper. They probably don’t have all the skills to make it happen, because maybe you’re a developer, so you can code somewhat, but you don’t know anything about running a business or how to market or how to pitch or et cetera. Maybe you’re a writer and you have a good idea and you can actually do some of the marketing, but you can’t really create the actual product.

Luis Magalhaes:

What does the roadmap look like? How do you go from that concept of a business in a piece of paper, probably like half a page and build a roadmap to make it happen through your community?

Andrew Hutton:

I love that. I love that. That roadmap is, I don’t know, it’s my favorite thing. It’s both a roadmap and it’s maybe more so a mindset and a set of habits. As a way of working and going forward, knowing that you actually don’t know what the road looks like. You have a compass more so than a map. You can set directions for yourself and you can stay the course, or you can keep putting one foot in front of the other, more so than having a map that says, “This is how it goes.” But to also come back to the idea that you’re absolutely right, the first thing that we guide founders to every single time is, get your ideas on paper in a worksheet, canvas way.

Andrew Hutton:

We have something that we give founder’s that helps them unpack their idea, so they can see the forest for the trees, helps them see all the different variables that they’ll have to play with as they build their business. It’s their first set of assumptions. I think these things are true, now, let me go figure them out. That mindset is your first compass. What do you think is true, and then how do you know it and how are you going to go figure it out, prove? That’s where the word validate comes in. Your compass in the early stages is all about validating these initial assumptions.

Andrew Hutton:

You’ve probably heard these words and this language before. Pretty standard startup stuff. It’s not very differentiated in saying it, but it’s all in the practice. There’s really two major muscle sets, muscle groups that you need to go do that. One is your ability to stay close and understand and talk to your customer, and learn from them and really follow them. This is where you might put on your design thinking hat. That’s where I got my start in my career is design, design thinking and how do you bring the empathy?

Andrew Hutton:

How do you listen? How do you not bring your assumptions into a conversation with a customer, but to let them tell you what their problems are, what their constraints are, what their needs are, whatever that might be? That’s the first thing. If you can build that habit and that muscle, you’ll be great because it’s also the beginning of how you go find customers, and how you go market your business. You’re selling to these people. If you’re understanding what their problems are and you’re building for them, you’re eventually going to sell to them, so you need them close.

Andrew Hutton:

Getting out of the building, this is Steve Blank school of thought is, where all the real learnings are and it’s where all the magic happens. The first thing that founder’s need is, they need the ability to talk to customers, get out of the building, fearlessness on the, “Hey, I’m going to listen to you and not bring my agenda into this meeting.” That’s compass number one, mindset, muscle group, number one. The second is the ability to ship something. The ability to, and now when I say ship something, it’s where prototypes, MBP is, again, all these other buzzwords. It’s the mindset.

Andrew Hutton:

It’s the attitude that when I create things, I’m going to create things quickly. I’m going to hold them loosely. What somebody tells me about them is what matters most versus what I thought the thesis that went into this little thing. Again, the smaller, the better. The more minimal, the better, because it means you get to go faster and you get to put more shots on target, and get things out into the world. If you go from understanding your customer, you might think you need to have a dozen customer interviews.

Andrew Hutton:

I’m telling you you’re off by 10X or 100X. You need hundreds to thousands of customer interviews over the course of the early to middle days of your business. When you talk about prototypes, there’s not like hundreds of prototypes, [crosstalk 00:30:09] but you need to be shipping at a scale.

Luis Magalhaes:

Sorry. Let’s dwell a bit into this, because this is interesting. I think that most people will listen to that, and it will register as something that, “Oh my god, this is right. This makes total sense.” But then a lot of people don’t have the smallest idea how to go about setting customer interviews, right? How would we get our potential customers to talk to us? Especially …

Andrew Hutton:

You’re totally right.

Luis Magalhaes:

I can get my mom and my aunt on board, but 100 strangers? Delve a bit into the micro here.

Andrew Hutton:

Yeah. Yeah. Love that you’re pushing for that, because it seems, when I say it like that over a couple minutes, it platitudes, right? It’s in the micro, how do you do it? The first thing that we coach people to do, so this is a whole module inside of Day One. You basically say, “We’re going to push you. We’re going to help you get past that resistance to get out of the building and get talking to folks.” Frankly, the first thing you have to do is, you do have to create a hypothesis. Who do you think your customer is?

Andrew Hutton:

If you Google persona template, you will find dozens of ways that you can write down who you think your customer is, step number one every single time. Write it down, because otherwise you won’t know who you’re talking to. You won’t know if your mom, your aunt or your neighbor or your colleague is the right customer. You have to have a thought, otherwise you’re nowhere. You’re going to spin your wheels. Put it down. Everything about this is also getting it out of your head, getting it on paper, because now your friend, your fellow entrepreneur can give you some ideas.

Andrew Hutton:

They might not be your customer, but they can say, “Oh, I know that person. I can connect you with that person.” Put it down and then start to share it. Both start to share it as an actual document with some trusted friends and then start to share it more as a, “Hey, is anybody a new parent, who has been shopping for thousands of strollers and cribs and a hundred things?” You put that maybe on social media. You put that out to your friends and your family. You put that out to maybe you’re in a community; maybe you’re in Day One.

Andrew Hutton:

Get it? You’re in groups, and you can ask folks, you put a little bit of your hypothesis out there and then let people come to you. We’re getting to the levels where the art definitely comes in, how do you not give away too much? You don’t want to cloud people. You don’t want to say, “I want to talk to people who had a hard time buying a crib.” That’s an assumption. Does everyone have a hard time buying a crib? Is it really hard to buy a crib? Maybe you did, but whatever. You can’t give away the store, but you have to get people in with enough of a hook.

Luis Magalhaes:

sleep on the floor, like, “Hey, what’s the problem”

Andrew Hutton:

Now, you’re hooking, right? If you start to go down this path and you’ve got your hook out on social media, out on Hacker News, Indie Hackers Product Times, whatever it might be, you want to put this on product Times. You are now beginning to get people in. again, I can keep going. There’s a 100 other all on tactics here. You might have a survey to see if the person’s the right person for you. You might just use a Calendly link to get them to talk to you. You might just start emailing with them.

Andrew Hutton:

There’s 100 other ways to go about it, but you’re looking to get them in a room with you because that’s where you’re going to have real, high bandwidth learnings. Again, we can keep going, then you’re going to have a questionnaire. You’re going to have a doc. You’re going to have a synthesis doc. There’s a whole workflow here that … Here’s the thing, it’s teachable. It is teachable. If you’ve never done this before, there’s a way to go up the learning curve. But it’s also just about practice, just doing it and doing it and doing it because it’s an art and people spend their whole careers getting good at user research.

Andrew Hutton:

Actually there’s one premise that I’ll say to you, I’ll kind of lay out there. The idea of a roadmap is interesting for sure of like what does a startup founder need to do in their first six to nine months? It’s maybe more important to say, “What do you need to get good at? What skill sets and what problems are you going to have to solve as a founder?” I’ll tell you, it’s way more than you think. You need to become a user researcher. You need to a product manager. You might need to become a “developer”. I’ll use air quotes around that because you might use no code.

Andrew Hutton:

You might prototype in some very scrappy ways, and that’s great. You’re going to have to build something. You’re going to have to become a financier and build a financial model. You’re going to have to have some legal, put a legal hat on and almost certainly get a lawyer to help you with that. You’re going to have to become a marketer. You’re going to have to become an HR person. You’re going to have to become a recruiter. You’re going to have to become a fundraiser. There’s dozens of skill sets.

Andrew Hutton:

Maybe there’s a dozen key skillsets that if you’re going to be a founder, you might be good at one or two of them. You might have some innate abilities. You might be a good storyteller. You might be fearless, whatever it might be. But translating those into the specific skills that successful founders have is a journey. To start as daunting, but the only way to build these skills is to start. There’s a catch 22. You probably don’t know what you don’t know. You’re probably fearful. You don’t know how to start, but until you do, you’re just going to be on the wrong side of the starting line. It’s-

Luis Magalhaes:

That’s almost becoming a one-man army and I totally get it. It makes sense because when you eventually have people doing that for you, it helps to have a knowledge of what the thing is about. Even if you’ll have … I don’t where this quote comes from, but I usually say that when I hire people, I hire people that are better than I at the thing, otherwise there would be no point in hiring them. I want to be the stupidest person in the room on the subject that’s being discussed. Maybe I’m the best generalist in the room.

Luis Magalhaes:

Ideally, that would be the case, but when it comes to specific topics and specific knowledge, if I’m not the most incompetent person in the room, then I hired wrong. When is the time in the project, in the startup, in the business’s lifetime that you seek to find people to delegate? When do you start building the team?

Andrew Hutton:

Yeah, you’re absolutely right. You’re absolutely right. You need to be bringing on people better than you at things. There’s two modes of how you get past yourself. One is, when you think about bringing on co-founders, which happens early on. How do you bring on a team at the very beginning? Then eventually you asked the question of how do you start to hire? How do you start to bring people on for maybe specific functionalities or specific roles to do those things? But you’re right, the top line premise is that as a founder, you really do need to be good at a lot of these things.

Andrew Hutton:

You really cannot, and I’ll tell you, you really cannot outsource before you’ve understood almost all of those functions. The exception is maybe a co-founder. If you and a co-founder can operate as one person, and I mean, have a very tight bond, basically we’re in this together, we’re splitting things 50:50. You take that, I take this. Then they take that right. Someone over there, this co-founder can be your head of product or your head of operations and know how to do all the legal stuff and all financial stuff.

Andrew Hutton:

That’s probably the only scenario where a founder can maybe not be very adept at a thing, because they have somebody who’s going to be in it with them skin in the game, all the way to the end with those skillsets. You and or your co-founders need to have all these skillsets. It seems like a high bar, but it frankly just is. I’ve never seen a founder succeed who … Here’s a common example. Most founders don’t come from finance backgrounds. If you come from a product or engineering or marketing, you may know how to use an Excel spreadsheet, but you’re not like a banker.

Andrew Hutton:

I’ve never seen a founder succeed who doesn’t intimately know their business model. That means they had to learn it. They had to learn how to read a spreadsheet, how to understand the ins and the outs of every line item of their business model. If that’s you, just go and learn it. You just have to learn it. I’m just saying, you really are going to be not just at a disadvantage. You’re probably shooting yourself in the foot, if you don’t understand at least the basics; if not intermediate level financial modeling. Same with marketing.

Andrew Hutton:

I’ve really never seen a founder succeed who didn’t know the basics of digital marketing. I’m saying these things like, you actually do need to be a polymath. You do need to be really broad, but we live in a world where that’s very learnable. There’s courses, there’s videos. You can go practice these things. For 50 bucks, you could go do a course and get a bunch of financial model templates. There’s no excuses is what I’m getting at. There’s no excuses. Being a founder is not easy. It’s a high bar. You need to be a marketer.

Andrew Hutton:

You need to be a financial person. You need to be a product person. You need to have enough sense of legalese to know how to go and operate. If you’re not that, you’re basically, I don’t know. You’re setting yourself up for a harder road, because I’ve really never seen a proper startup succeed, where you’re outsourcing things so early. This is what happens when you come from family money and you just get to spend it. It’s not ideal. You can take a big fortune and make a small fortune out of it that way.

Andrew Hutton:

Maybe you’ll get a business along the way, but it’s not necessarily what we’re talking about here. You feel me?

Luis Magalhaes:

That’s building the business as past time right?

Andrew Hutton:

Exactly.

Luis Magalhaes:

It’s like, “Yeah, I’m ROI negative, but I have a business. I am a business person.” Right.

Andrew Hutton:

Yes. Yeah, those skill sets, the building … Don’t even talk about when you hire the team. But maybe one principle you can take away from this is, hire somebody after you’ve understood it at least a little bit, if not a lot of it. I’ve tried it the other way, and you’re trying to learn things from somebody you hire, the odds are you probably are hiring the wrong person because you just don’t know. Maybe that’s the way you go up the learning curve. Maybe it’s an important thing that you need to hire somebody right away to do it.

Andrew Hutton:

Be ready to have some stumbles. Because not because that person to hire is bad, but because you just don’t know. You might have the wrong person in that marketing role or in that product role. Just coming back to the idea of building in a sustainable way, building a sustainable way allows, gives you the time to go up these learning curves, to learn the things that you’ll need to learn. It’s a much more firm foundation for when you start to accelerate or the business starts to work.

Luis Magalhaes:

What about hiring for experience or even for reputation? Let’s say that you’re in an industry, but you don’t really … You have an idea that targets a specific industry, but you don’t have a lot of cache, a lot of reputation in that industry. Does it make sense to get people on your team that probably have more experience in that industry, and that want to do something new within that industry? How should founders consider this, consider the pros and cons?

Andrew Hutton:

Yep. If and when that’s an issue, that’s probably a co-founder situation, because, yes there is a world where you kind of … it’s either a co-founder or it’s a consultant. Meaning, it’s either somebody who whispers in your ear and helps you navigate the ins and outs of healthcare regulations. Or if it’s so existential to your business that you must have it, and you’re trying to pitch investors and you say, “Hey, I’ve got this consultant who helps me.” That doesn’t count. It has to be basically like I said, you as a founder need all these skill sets.

Andrew Hutton:

If industry knowledge and know-how and reputation is existential to the business, it basically has to be on your team, which means early days it has to be a founder or rather a co-founder. There’s lighter versions of that. I’ve seen this in healthcare a lot. I’ve seen most businesses that get off the ground in healthcare have a founder, or co-founder from the industry, a doctor, somebody who’s worked at pharma companies. I’ve also seen them hire consultants to do other things related to healthcare. Healthcare is a sticky top industry, but yeah.

Luis Magalhaes:

They know something about that, yes.

Andrew Hutton:

A hire generally doesn’t work, because they could leave any seconds.

Luis Magalhaes:

You think that a hire doesn’t lend enough credibility?

Andrew Hutton:

No. Yeah. Yeah. I’ve seen people try to use advisors for this. Again, sometimes it can work, but again, [inaudible 00:42:59] depends on what’s the essence of it. Credibility, reputation almost certainly needs to be at the co-founder level. If you need someone to advise how you build out your process, again, maybe you can have some PhD who’s got a big name come advise you as a consultant.

Luis Magalhaes:

It just feels to me that if you’re building something, being able to say, “We have this person on our team that has successfully brought to market three products,” let’s say something like that. It does seem that that could be inspiring, not just for investors, but even for clients, right?

Andrew Hutton:

Maybe. Every time I say something so concrete, I start walking it back because there’s always these edge cases. You’re totally right. But if I’m walking into a client or investor meeting and I’m talking about the skills of my team, I guess I could see it. If I’m building an agency, my team is my business. My team is my product. My team is what I’m offering and they can’t all be co-founders. So yeah, there is a point where you say like, “Man, we’re the best. We have an A team here. This is a group that you can trust.” To be fair …

Luis Magalhaes:

Maybe I can specify, chisel the question a little bit. I guess that the question eventually is, do you think that on average, again, there are no definitives, but do you think that people buy more the product or the team behind the product?

Andrew Hutton:

Yes.

Andrew Hutton:

Yes. Again, I would say if you’re actually a customer, it’s almost certainly the product. It’s definitely product first and there’s some, in a B2B world where you’re like, “Well …” If you’re an early stage customer in a B2B startup, you’re like, “These guys better be able to build what they’re selling me,” because it’s probably not even fully built yet. You’re buying into the trajectory. In that sense, they’re putting on a little bit of the same hat an investor would. Investors probably do invest more in team, team and then the idea of the market, meaning the problem you’re solving, because the solution probably will change.

Andrew Hutton:

If you have a good team and a good problem, the solution changes, the product changes and that’s fine. That’s the nature of going ahead, pivoting, building the business. Yeah, customers though can’t see them not paying attention more to the products and the team is the product, like an agency or a consultancy.

Luis Magalhaes:

Now we get to the part that I’m always super interested in listening about. I mean interesting in all of this of course, but specifically for the DistantJob show, we’re talking already about building a team, about finding the people who share the vision. To be specific, motivating these people across what is a very tough endeavor like we said, there’s the resistance that startups usually, especially if they’re bootstrapped, the resources are limited. You just buy a superhero for every part of the team. You need to juggle your strict resources.

Luis Magalhaes:

In a fully remote work, how do you see better teams being built and not just being built because hiring the people is just the first step? That’s actually the easiest step. Just to self-promote a bit, you get the recruitment agency like this and job to do it for you. But then once everyone is actually on the zoom call, right on the Trello board, on the base camp project, whatever, how do you make those people enthusiastic, and dare I say, dare I use the ugly overused word, productive?

Andrew Hutton:

That’s a big one. I would say, I ascribe to your sentiment that the first part of getting the person is easy. In fact, I think it has been made easier, given that we’ve all now experienced what it’s like … You take a team, you make them remote, you realize, “Huh, I don’t have to be hiring just in New York City. I can hire people in the outskirts. I can hire people in Ohio. It doesn’t matter.” There’s almost certainly a better moment these days to finding the right person, because yeah, we’ve truly expanded our view. There’s much more liquidity in that market. The bringing them together is [crosstalk 00:47:23].

Luis Magalhaes:

That’s what I said on my website. Actually, are you reading from it?

Andrew Hutton:

I wish. No. But I’ll tell you, I think it breaks down into two things. Life is much, much harder when you’re early stages and you’re trying to figure out the what, the direction. When you have to innovate, it is hard to bring everyone to figure that out, when you’re not in a room together when you’re not jamming on the whiteboard. If it’s a little more tactical, then there’s been remote work companies that have succeeded being more execution oriented. They’ve been living that life. Yeah, I would say, if I have any advice or solutions for how to bring a team together, it’s jeez … When I think about how we bring folks together within Day One, or even just how our team has come together …

Luis Magalhaes:

Please, that’s what we’re for. Tell me about it.

Andrew Hutton:

It’s not about the tools. We use all the standard ones, Zoom, Slack, everything else. I think your culture does shine through. Meaning, the specific things you do to build culture shine through. I say without necessarily being an expert at them, you have to build those in. You have to do more of those things. You can’t just rely on the ad hoc, hanging out at the water cooler getting a coffee or even drinks after work. None of those things will happen organically in our spread out world, so you have to be 100% more intentional.

Andrew Hutton:

We think about that when we’re bringing entrepreneurs together. People won’t necessarily just like buddy, buddy up, even if they’re in the same community or cohort. They will absolutely need to be brought together in intentional ways, whether that’s … Again, the idea of a zoom happy hour is definitely over baked, so you just have to keep going orders up. Okay, so we’re going to create the happy hour. Well, that’s lame. What do you do? How do you create the fun?

Andrew Hutton:

How do you create the energy? One thing that we did, I’ll say this isn’t what we do at Day One, but it’s what we did at Human Ventures is that one of my last few months there, before we, as we were going remote, as Day One was getting spooled up on the side is, we had daily stand-ups with our team. Daily stand-ups with our team focused, not at all on work, but everybody bringing a little bit of their human, their daily life into the picture. Sometimes that was like, “Here’s this book I’m reading. Let me tell you what it’s about.” A bit of a forcing function.

Andrew Hutton:

Everyone had to go on a certain date. You have to do things like that. You have to force people into these moments.

Luis Magalhaes:

this time, go.

Andrew Hutton:

Exactly. But then people started to get fun with it. They showed like, “Here’s what I made for dinner last night, or I made my favorite meal and I recorded it, or here’s my favorite recipe or, hey, let’s all talk about our favorite vacations we took last year or two years ago now.” The idea of a daily team building stand up, actually it fizzled out months into it, because it is indeed hard to maintain for sure. But for a moment or for a while, it was really, really valuable for keeping some cohesion, obviously as a place for updates, things like that too.

Andrew Hutton:

Yeah, you have to be intentional. You have to create new spaces for it. I’m talking about the cultural aspects here. To have some sense of connectivity, which is where all those like, “Okay, now I just know this person. I don’t feel weird reaching out, because they’re not just colleagues. We have some shared connection.” It’s building those types of bonds that are I think at the root of this idea of productivity in a remote world. It’s not just purely transactional and functional. That’s my best one for you.

Andrew Hutton:

I think we very much believe that relationships drive learning and productivity. Building relationships, even if it’s just amongst coworkers is probably the thing that you can do that will pay dividends down the road.

Luis Magalhaes:

Does it make sense … Obviously; my whole shtick is that you can find the best people in the world by looking remotely. If you recruit remotely, you have the best in the world at your fingertips that you didn’t need to be restricted by location. But at the same time, I have this intuitive feeling that if I’m launching a new business, if I’m launching a new startup, I actually want to try to hire people I’ve worked with before, if this makes sense. What is the balance to be struck there?

Andrew Hutton:

Yeah. Again, I think in this world we live in today, you don’t need it. To be fair, it is beneficial if people come from maybe the same, I won’t say industry, but culture, meaning do they get startups? Have they worked in startups? Are they in the same Twitter sphere as you? Things like that. That kind of counts as a shared cultural backing. Knowing them is the next level. Hiring people you know is obviously the hack everyone does. Sometimes investors look for it, do you have people that you can bring with you?

Andrew Hutton:

Are you a leader and can you bring people into your business that you know? Because investing in a loner is maybe a bad idea. All that said, it definitely doesn’t allow you to kind of … You’re probably good friends with people who are like you. It doesn’t usually create diverse teams and diverse environments and it’s definitely limiting your pool. Anytime somebody is basically starting with their friends and people they know, it’s a trade-off, it’s efficient. They already have relationships. They already know those skills, but they haven’t done a search to go find people who may be better.

Andrew Hutton:

They haven’t built the diversity into their team usually. The essence of it is yes, like all things a startup founder is doing is they’re being scrappy in the very beginning. They’re doing what they have to do to survive. I’ve hired friends, absolutely. But eventually all things a founder does is they build foundation. They build process, they build for the future. I won’t say founders should mortgage their future just to get started. But it’s a really tough balance, because a founder … Tomorrow is not promised for a founder.

Andrew Hutton:

You really can’t necessarily overinvest in the future until you’ve started. When it comes to hiring, that’s a tough one. Hiring your friends, shortcut, best long-term thing, jury is definitely still out.

Luis Magalhaes:

Okay. Okay. I just realized that I lost track of time, as [crosstalk 00:54:08]-

Andrew Hutton:

We’ve gone for a while. It’s been fun.

Luis Magalhaes:

… interesting conversation, I don’t really have a strict deadline, but I want to be respectful of your time. I think if we jump to some rapid fire questions. The questions are rapid-

Andrew Hutton:

Let’s do it.

Luis Magalhaes:

… but the answers need to be, and then maybe I can have you in the future for a round two where we talk-

Andrew Hutton:

I would love it.

Luis Magalhaes:

about the way you work at Day One, because we barely touched that.

Andrew Hutton:

I would love it. No. I think these ideas are amazing. They’re fun to jam on and let’s do the rapid fire, because I’m definitely coming back around too.

Luis Magalhaes:

All right. What are the apps that you start your day with? What are the browser tabs that you have open as soon as you start your day?

Andrew Hutton:

Oh my gosh.

Luis Magalhaes:

[please.

Andrew Hutton:

My core browser window has Trello, Gmail and Google Calendar. I think my life is dictated by what’s the top of those three things. My Trello board, which is maybe the most strategic, my Gmail which is who wants my time right now, and then my calendar, which I’ve set up a week ago, tells me what today is like. Definitely a very bad productivity stack. Other than that, probably Twitter, just seeing what happened overnight.

Luis Magalhaes:

Sounds great to me. Let’s go a bit into calendar porn. How do you organize your time in your calendar?

Andrew Hutton:

I have started trying to stack up meetings on a day, and so a week or two in advance, I start to see which day has already started to be my meeting day and then I just like lean into it. I’m not super strict on it must be Friday, so a day today has a bunch of meetings and it’s fine. Because then I remove the context switching, but I kind of balance the meetings, the Day One fellowship, working with founders and sessions we have, and then some deep work, trying to carve out days or chunks of time.

Luis Magalhaes:

Okay. If you had $100 to spend with each person working with you and the rule is you can’t give them the money directly or an equivalent, like a gift card, what would you give them? You need to buy the same thing for everyone essentially.

Andrew Hutton:

I would buy them probably some booze, probably some nice wine or whiskey or a bottle of house, the] for something fun. I think that’s what I would want. That’s what I’d probably get.

Luis Magalhaes:

I know. I’m a fun. I’m a fun right? Love it, love it. What about yourself? It could be booze the answer as well, but what purchase has made your work life easier or more productive in the past year?

Andrew Hutton:

I think a bunch of things around our apartment that have made life a little more enjoyable, some plants. I like to move around from the couch to the desk, and so a little lap desk thing was really valuable. We recently moved and so threw a ton of things away and put stuff into storage. We’ve definitely upended our life at the moment, but … Oh, I’ll tell you the one thing that we got in the last year, is we got two cats. We have some pets, which allowed connection, some physical, human, not human connection over the last months when we didn’t get to see anybody, so yeah into our family.

Luis Magalhaes:

I’m fan. My pets are absent, oddly absent from this zoom call. They are usually a fixture. They’re probably napping somewhere definitely. I am a fan. It’s very relaxing. Let’s talk a bit about books. Are you a book gifter or do you like to gift books?

Andrew Hutton:

I don’t, but I know that’s the aspiration.

Luis Magalhaes:

You like to read books, and it’s okay if you don’t right?

Andrew Hutton:

Again, I like to read books. I actually am very much always looking for somebody to just put a good fiction book in front of me, as a way to vege out versus necessarily just watching TV or something. I’m definitely a fan of a good spy novel, a lowbrow way to get lost in an idea.

Luis Magalhaes:

Any recommendations for our audience?

Andrew Hutton:

No, I’m looking for recommendations. I know the classics, John le Carre and Tom Clancy, but I don’t know how to navigate the top 10 lists. That’s what I need. I need recommendations. Follow me on Twitter and tell me what books you’re reading, because I need them.

Luis Magalhaes:

Me too. Awesome. Awesome. Okay. The final question is directed towards a bunch of people that aren’t necessarily your audience, but I still like, because it’s about remote work, I’d really like to have your input on it. Here’s the set up. Let’s say that you are hosting a dinner when it’s okay to host dinners again. We’re not advocating anything against the law that goes against your local or state law. Anyway, you’re hosting a dinner in a Chinese restaurant, and during the day there’s going to be a round table about remote work and the future of work.

Luis Magalhaes:

In attendance are going to be the leaders and the decision makers at top tech companies. Now, because you are the host and this is at the Chinese restaurant, there are fortune cookies involved, and you get to pick the question that goes inside the fortune cookie. What is your fortune cookie statement, question, whatever you want to put inside?

Andrew Hutton:

I’m just going to steal a little bit from first Jeff Bezos and then maybe Peter Teal. Jeff Bezos question is what’s not changing in the next 10 years that we can build for? Then the Peter Teal question is what do you believe that no one else does?

Luis Magalhaes:

Nice.

Andrew Hutton:

I want to stretch people in those fun ways. Those are ways that I’ve felt stretched. I do think they lead to big picture thinking and answers, whether it’s related to how we should build our businesses or which businesses we should build. Not following the normal trends, norm for just like what’s hot today is, I don’t know. I play the game, but I’m a little sick of how trendy things have gotten, and I’d much rather build for the distant future and where we need to be.

Luis Magalhaes:

I agree. If you’re going to steal those good places to steal from.

Andrew Hutton:

Exactly, great artists. You know what they say about great artists.

Luis Magalhaes:

Exactly. Thank you so much for being a part of this interview, for coming on the DistantJob Podcast. It was an absolute pleasure. Where can people find you? Where can they continue the conversation with you and where can they learn more about what you do and what Day One does?

Andrew Hutton:

Absolutely. You can find me Twitter, LinkedIn, would love your connection request or just a follow. I’ll follow you back for sure. I think just search for me you’ll find it. Day One is at www.joindayone.com. Definitely a place to find information, find content, reproduce, find the application and deadlines and different things like that. Please show up there, drop us a line. Would love to get in touch and help you find out if Day One or one of our programs is a fit. Please come on by.

Luis Magalhaes:

All right. Andrew, it was an absolute pleasure. Thank you so much for being in the show.

Andrew Hutton:

Likewise, thanks, Luis. Thanks for having me.

Luis Magalhaes:

Thank you for listening to the DistantJob Podcast, the podcast about building and leading us in remote teams. See you next week.

Luis Magalhaes:

And so we close another episode of the DistantJob Podcast. If you enjoyed the episode, please you can help us out by sharing it on social media. That would be great. It’s how we reach more listeners, and the more listeners we have, the more awesome guests I can get in touch and convince to participate in these conversations that are a joy to have for me. I hope they’re a joy for you to listen to as well.

Luis Magalhaes:

You can also help a lot leaving reviews on iTunes or your podcast syndication service of choice. Reviews are surprisingly helpful in helping the podcast gets to more listeners. Now, another thing that you might want to do is go to distantjob.com/blog/podcast. Click on your favorite episode, any episode really and subscribe. By subscribing, you will get a notification whenever a new episode is up, and whenever we get the transcripts off the episodes up so you can actually peruse the conversations in text form.

Luis Magalhaes:

Of course, if you need to find a great employee for your team, a great remote employee, you should take the whole world into consideration and not just look to hire locally, not just look to hire in your country. Look around the whole world, because that’s the talent pool that contains the best talent. To help you with that, again distantjob.com is the perfect place to start. You will tell us who we need, and we will make sure that you get the best possible candidate, 40% faster than the industry standard. With that, I bid you adieu. See you next week on the next episode of the DistantJob Podcast.

More ways to listen:

We’re experiencing a transition in the way people work. The office environment is changing towards a more digital modern work environment that has its perks but also its challenges, especially for entrepreneurs who are starting to build their startups.

In this podcast, Andrew Hutton, shares how he launched his remote startup during one of the most chaotic years for many. Despite the pandemic, he was able not only to build his business successfully but help other entrepreneurs doing it as well.

You always need people. If you look at places where startups were formed, what typified them was the fact that there was a culture, people who are all culturally of the same mindset that we're sharing ideas and helping each other out. Click To Tweet

Highlights:

  • Dos and don’ts of building a remote business.
  • Mistakes to avoid when building a remote startup.
  • How to get past the resistance from building a business.
  • Bootstrapping vs VC funding.
  • Insights on early competition for startups.

Book Recommendation:

  • John le Carré books
  • Tom Clancy books

 

Don’t forget to SUBSCRIBE so you won’t miss all of the other interesting episodes that we have coming up in the next few weeks!