Meet Joshua Gross
Founder of Planetary — a NY based Digital Agency!
The Come Up highlights successful business owners’ & operators ‘come-up’ stories in an easy-to-read, written interview format. All content is transcribed from live interviews.
Know someone who would make a great interview? Nominate them here!
Or, if you’re building a business of your own and need some support, we should chat!
For this issue: Josh Gross, Founder of Planetary — an NY based digital agency!
Planetary Quick Stats:
📅 Years in Business: 11
📈 Projects Completed: 200+
💰 Revenue Generated for Clients: $50M+
👥 Head Count: 25
🏦 Annual Revenue: ~$5M
🎯 Target Profit Margin: 40%
📊 Actualized Profit Margin: ~30%
🚀 Best Growth Channel: Referrals
🏆 Best Quarter to-date: Q2, 2024
📉 Worst Quarter to-date: Q4, 2020
🛑 Times he almost quit: More than he cares to count
About Planetary
Planetary is a digital agency that works with clients who are in the process of evolving from wherever they've been to wherever they need to go, digitally-speaking.
Usually, that means redesigning websites, re-platforming digital products — building something blue sky for them from a design and development standpoint.
The short version is we help companies whose market or customers are changing…
Maybe they've expanded into new verticals, maybe they've shifted their sales focus, customer focus, marketing focus — but in some way, the business has changed substantially and they now need to change their website, their product, their mobile app, to meet the new needs of the business or the new needs of the market.
How it all started
I started writing code at like nine years old — my first freelance gig was at twelve.
I did a lot of open source stuff for fun as a kid, built some open source software, released some projects that got some attention early on, which gave me a lot of verve to keep pushing on this, and also got me some of my earliest freelance clients.
I freelanced for a long time, throughout high school, throughout college. Post college, I ended up going the traditional path, applying for a bunch of roles…
I landed a job working as a developer at a startup for about a year, and realized I hated it: I did not enjoy working for someone else. For better or worse, it was a struggle for me. So I quit, went back to freelancing to explore what I might want to do with myself.
I did freelance work for a few years and got to a point where I realized that I could be more impactful if it wasn't just a one man band — me doing everything alone.
Between taking on design projects, taking on development projects, managing the finances of the freelance work, and just trying to do everything, it was way too overwhelming, even though it was fun and the work was exciting. So, I brought on super talented folks that were better at each one of these individual areas than I was.
From there I realized that there was a need to scale.
I didn’t want to end up in this limbo of freelancing, but also having folks under me. It can easily be a no man's land of work where you're never really quite admitting to yourself that you're running an agency, so I just jumped in and was like, well, I'm running an agency now. Let's just go whole hog.
Freelancing vs. Running an Agency
As a freelancer, I was definitely stressed at first, largely because I like having a steady stream of work.
Anytime a project would end, a client would fall through, or I didn't win something, I would stress out — it didn’t matter how much work I had.
There was this perpetual sense that it was all going to dry up all of a sudden, and that I needed to just keep collecting as many new clients and projects as I possibly could.
I don't know if that was a good driver for how I ended up starting the agency, but that stress was always there, regardless of whether or not I had anybody else working for me.
I know there are a lot of freelancers out there that are very much “take it as it comes”, where they work one or two projects at a time, and it's not as stressful.
I never operated that way for whatever reason.
Starting the agency initially, I used contractors exclusively. But it quickly got to a point where I realized that I needed to retain knowledge of the approach beyond just me alone. That was going to make a huge difference in how the agency operates and how clients see you as you scale up.
Like, how does that knowledge get transitioned from between teammates?
How do you build a team around certain ideals?
So I built that up very slowly. It started with just one person, then two, and we stayed at like two or three folks for a while, full time, and then everybody else we would continue to fill out with contractors.
We've been very intentional about growing the full time team because it's more cost effective to have full time in some ways, but it's obviously a huge risk in other ways. You have to make sure you have a steady baseline of work to afford the downtime.
But having that full time team makes a huge difference in setting the tone for how the work gets done and making sure that you have a continuous set of folks that are thinking about the processes. People are actively thinking, how do we make this work in a way that is sustainable as we grow? We still use a lot of contractors, even today, but we've grown that full time staff considerably.
Finding a Niche
We started off very, very broad.
When I started the agency, we took on whatever clients we could get. Thankfully, I had years of freelance work, so I could go back to those connections and just try and seek out more work from them and use that as a basis from which to continue growing the agency.
Over the years, we've narrowed the work and tried to be a little bit more specialized than we have been, historically.
Back in 2013-2014, it was almost easier to go as broad as we did because, while there were a lot of big agencies, there were fewer small ones…
The competition wasn’t as intense.
Now, there are a million tiny agencies and it’s gotten to the point where a lot of us are competing for the same projects.
Because of that, we've realized we need to specialize more, and we've narrowed our focus to website redesigns and website replatforms. That extends to technologies, too. We've partnered with Sanity, the content management system and Next.js as our core tech.
You can go broad if you have the relationships and scale, and a lot of these big agencies still go very broad. But I think as a smaller agency especially, we've needed to focus on our specialization so that we can double down on partnerships and relationships with the right folks — ones that will be sources of new business for us.
That's not to say those partnerships are our only source of new business: a huge percentage of our new clientele is still referrals.
It’s like laddering up, essentially: Building strong relationships with folks that have slowly advanced in their careers and gone to bigger and bigger businesses and higher levels and they still want to work with us.
We become their go-to, which is awesome.
Or, just being able to get referrals from one business to the next, because a person that we worked with at ‘brand A’ really liked us and wants to share us with their cohort at ‘brand B’.
These days, we've narrowed our focus. We've limited the things that we do, and the things that we don't do.
Ecommerce, for example, is very much outside our wheelhouse. We don't even really get these leads, but the times that we do, we'll refer those things to other agencies that are better suited for that work.
We’ve narrowed in our focus and doubled down on the relationships that we do have both with our partners and with folks that we've worked with in the past. And that's become our two key new business channels.
Then, of course, there's the broader network of people that we interact with from time to time, both on things like LinkedIn and social media and other events, but that just becomes the outer edges of our network of referrals.
Long-Term Vision
Ultimately, my goal is to build this into a business where I don't have to necessarily be a key part of the day to day. I don’t want business to suffer if I'm not there for one reason or another.
I think key man risk is a hard thing to deal with for folks building small agencies, so my goal over the past few years has been to build more systems around me.
In practice, that’s finding the areas where I need to hire myself out of the equation, or develop more concrete processes to make sure that the team that we have knows how these things operate.
That way, I can focus on continuing to grow the business, but at the same time, if I needed to leave for a couple of months, things would continue operating without me, and nobody would miss me.
I've invested a lot of energy in trying to get myself out of that position, and it's working. That being said, I think it is definitely a long process to get there.
The first eight years of the business, my focus was on growing the business as much as I could. Now, it’s gotten to a point where it will continue to grow regardless, but I want to make sure that it’s a sustainable kind of growth.
I feel like with service businesses especially, oftentimes the founder is seen as the visionary, or the key person or that clients want to work with. That's why they work with the agency.
I don't want to be the reason why folks are working with the agency…
I want the quality of the work that we're capable of doing and the thinking behind it all to be the reason — not just, hey, this is Josh's agency, and we want to work with Josh.
For me, it's not necessarily about building the agency to make it sellable, either.
I’m not really interested in having it be passive or build an entire suite of agencies, but I do want the optionality to do any one of those things. If I'm a key person in my agency, I don't have that optionality, right? As soon as I can get myself to the point where I now have that option, I can look at those three things and decide which one I want to pursue.
Quite frankly, I'm not a passive person.
I like to be involved in whatever we're doing in some capacity, so having a passive agency is probably never a thing that I could even just get myself to do. I know I'm not capable of doing that, so either selling the agency or building a portfolio of agencies where someone acquires one or more of these things is the direction I want to go.
Overcoming Challenges
I mean, we were very fortunate up until 2020.
2013 to 2020 was basically a bull market. 2020 hit, of course, and that definitely put a wrench in that.
Thankfully, we've been remote from day one, and that didn't change anything for us in terms of how we operate, but COVID definitely changed how many opportunities were available to us.
A lot of their projects that we thought were going to happen suddenly weren't because everybody just pulled the emergency brake on pursuing new work — whether or not it made sense to do so.
I think everybody just kind of went into turtle mode and really wanted to protect themselves until they figured out what was going on.
That was honestly one of the most challenging moments for us because the business definitely suffered. We had to scale down a little bit, and it was probably one of the slowest years we've ever had, but we weathered it by scaling back.
Thankfully, because we have very good prior years, we're able to weather it out till the following year. So we kind of resumed the trajectory that we had been on, which was nice.
Besides that, the hardest thing — beyond broader macroeconomic stuff — is just getting the right people into the room.
Agencies are one of those work environments that often push people as hard as humanly possible and build teams that are — for lack of a nicer way to put this — disposable. I could see how businesses can operate like that, but my intention was never to operate that way because I hated working in those environment.
I’ve been trying to be very intentional about building a system and building a team that can work healthy hours and have a relatively normal work life balance.
That's been a very hard balance to strike because there’s this perpetual urge of throwing more hours at it, throwing more money at it, throwing more people at it, just getting it done.
I've seen agencies that put out amazing work, but then you find out how the sausage is made and it's not pretty.
If you feed into that notion, you churn through folks constantly, and you're perpetually filling an extremely leaky bucket of talent. I've seen a lot of agencies do that, and some of the best talent I've ever seen has quit because of that kind of environment — they do one or two projects and they're gone. You don’t want that.
We work really hard to make sure we build a healthy team and build a healthy set of processes around how the work operates and what the expectations are.
Business Development Habits
It's funny, since I learned how Peter Kang emails like 10 people per week, I have since stolen that as a habit.
Right now, we have this consistent habit of outreach.
For us, that is our monthly newsletter which includes a lot of current and past clients.
Once a month we're popping up at the top of their inbox and we're sharing something that's meaningful and actually useful. We try to share things based on what we've been seeing other clients do, things that we've been working on internally, or on the technology or the process side.
I don't go into these conversations with the intent of saying, hey, we want to work with you. Do you have any work for us?
I've seen a lot of folks do that, and when you do that, you're trying to catch them at the exact moment where they might have a project. Sending that email is like throwing a dart into a dark room and hoping you hit the dart board. It might happen, but it’s unlikely.
On the flip side, by just saying hello, you've made a point of checking in on them with no intent to close some sort of imaginary deal. Hopefully, the next time something does come up, you've spoken with them recently enough that you're top of mind.
Yes, it’s nice to remind them that you exist, but also — people appreciate that you've thought about them. I feel like everybody gets so wrapped up in their world all the time that it's so unique to just remind people that there's somebody else out there thinking about them.
It works incredibly well, but it's a thing that you have to do consistently over time because it compounds.
I’m really trying to be consistent about those habits week over week, month over month, even when we get incredibly busy.
If you fall out of that habit for a month or two, you're now essentially months behind in keeping up with that flow. And it might take 6, 12, 18 months for you to see any return on that “investment” of outreach and conversation building.
I said this to my team recently, but it's essentially like that quote: the best time to plant a tree was 30 years ago. The second best time is now.
The best time to have been consistent about building these relationships would have been the day after you met the person. But the second best time is as soon as you possibly can.
Creating Standard Processes
I look at this as essentially two different pieces: There's the business development — everything leading up to a contract being signed — and then there's everything after that.
I've spent a lot of time over the past couple of years working on the contract signing and onboarding portion.
This past year specifically, I've been spending more time building out what we call the client services handbook, something which essentially enumerates every single phase of a project, depending on the type of work that we do, like:
What are the expectations for each phase of the project?
What are the ways in which we communicate with the client?
What are the things that we produce at each phase of this project?
How do we handle different situations?
We literally have an entire section of our handbook called, “what to do when” and it's a bunch of common things that come up and all the different ways to handle them.
We’re really just trying to give our folks a set of tools so that when they don't know what to do, or when they're at a certain point in a project, they have a very clear picture of what needs to be done.
It's something that is constantly evolving over time, but that's been a huge boon towards getting me to specify what my expectations are for each phase of projects.
Having that handbook has been hugely beneficial to actually executing the projects from start to finish.
Then on the business development side — quite frankly, that’s still something I'm figuring out.
Right now, I’m just asking myself more questions, like,
What does it mean to develop those sales motions that we need to?
What are the sales motions that I do right now?
How do I codify those?
And then how do I fill the roles that will make that machine work?
Does that mean I need to hire social media managers?
Does that mean I need to hire someone that can handle new business development for partnerships?
There’s a lot to it.
There's also a few things that we're trying to figure out in that realm to turn it into a system that can operate on its own. Honestly, that might mean hiring a CEO that can do much of what I can in terms of the business development, and I slowly shift those relationships over to them.
I'm still figuring it out, but everything beyond that, we're starting to get a pretty clear picture of what those processes are.
Resources for Upskilling
Well, I graduated with a BFA, and I can tell you there was not a single bit of business management or finance management in art school.
I think that is something that should be added to the curriculum because a lot of the folks I went to school with ended up doing freelance in some capacity, and it would have been valuable for them.
For me, I was very fortunate in that my father is an attorney who has also started and run businesses before, so I was able to learn the basics of finance and contract management from him.
At twelve years old, I remember watching him redline things in contracts and then he would explain to me why he marked them up. That shows up now, when I spot things that need to be changed in our contracts with clients.
So yeah, I was very fortunate I had a leg up in that regard, but everything else has really been — for lack of a better way to put it — trial by fire, just forcing my way through it.
It’s also been leaning on acquaintances that have gone through some version of this when I can. A big reason I built up a network of folks that run agencies was because I wanted to be able to get advice on how to do or handle certain situations from time to time.
Otherwise it's been like gamble — failing a whole lot, getting up and then failing again until you figure it out.
From time to time, you read a book, try to learn something from it, or from somebody else who's done this or somebody else who has experience working with folks in this field.
It’s a mix of different things, but there’s definitely a lot of failing involved.
Lessons Learned
I think if I could wave a magic wand and fix any specific problem with the business, it would be having a really strongly defined process from start to finish.
I guess that goes hand in hand with what I would do differently if I could start all over again, but in many ways, I think I wouldn't know the process from day one.
Eleven years ago when I started the agency, knowing what the processes would need to be, I had no idea. I think it's different for every business.
Starting the agency with a more narrow focus would have really helped — not trying to be the jack of all trades that I was as a freelancer. Picking one narrow thing and then running with it would have made our lives a lot easier, and we would have scaled a lot more quickly because we started so broad. '
Folks didn't come to us for any one specific reason.
I think you can build a really strong pipeline based on doing one specific thing very well, because everybody knows you as somebody who fixes that one thing.
Yeah, if I were to do it all again, I would do that...
I would just pick a focus and run with it, because you can always go broader sometime down the road.
That’s it for issue this issue!
Please feel free to subscribe, or share your feedback on what you’d like to hear more about for future issues!
If you, or someone you know would like to be featured, or just want to connect, feel free to message me on LinkedIn, or, if you’re building a business of your own and need some support, we should chat!
Interview by: Alex Tribe
Edited by: Angus Merry