Building an Agency through Upwork...
⚡how Troy Tessalone built Automation Ace & optimized for lifestyle freedom...
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!
For this issue - an interview with Automation Ace founder Troy Tessalone!
Automation Ace Quick Stats:
🤝Business: Automation Consulting
🏆Upwork Total Revenue: ~$300k+ (Top 1% of Upwork)
⏳Years in business: 4.5
👥Headcount: 1
⏩Best Growth Channel:
Upwork
Client Referral
🧾Avg. deal size: ~$1,000
🤝no. of clients 650+
💻Apps integrated: 725+
Before Automation Ace…
Before this I worked at a tech startup in LA - it was a really fascinating business model helping Fortune 500 Brands do customer acquisition from search to sale, online and offline…
I was a technical product manager there, saw a lot of growth, got my hands dirty and pretty much did a bit of everything - it's the startup world so you're always wearing a lot of hats. But I hit a point in mid-management in some sense, stuck between doing and managing and honestly, I just got kind of burnt out.
It was like, all right, I need to recalibrate - decide what's next for my career…
I was making good money, I liked the idea and mission, but less so some of the politics and dynamics that can happen in those environments, right?
Plus, projects that I thought we should be able to do in two weeks were taking two months, and there was always shifting and competing priorities. Obviously the company has continued to be successful without me, but I decided to quit, do some soul searching, take some time away to travel and pursue hobbies, and reevaluate what would be next for me.
Quitting without a plan…
Honestly, I probably thought I had a more solid plan than I did..
Like I said, I intentionally took some time off during Q4 in 2018. I needed a break, wanted to travel a bit, and enjoy the holidays. I thought, "I'm a smart guy with a good resume, I'll easily find another technical product manager job in tech for some tech company."
After all, it's LA, and there are jobs everywhere… how hard can it be for me to jump back into things, right?
In the tech world, you always hear about people taking these little sabbaticals and time off - I just figured, this is my turn to do it!
So I took a few months, and in Q1 2019, started applying, and got the job hunt going. I got some good opportunities, did a lot of interviewing, and applied to a ton of positions but nothing landed.
Honestly, the job hunt is a job in itself - it can be really draining.
I was the runner-up for several jobs, and just got so frustrated and strung out from constantly looking at the same job postings every day, trying to stand out, preparing for interviews, and eventually, I started questioning everything…
I thought maybe it was a sign that I needed to do my own thing or figure out how to start making money again, right?
My financial resources were draining faster than I thought, since I figured I’d be back to work already so I really just thought “what am I gonna do?”
In between applying, I had plenty of time to figure out if I could start a side hustle, maybe do Uber or something like that, but truthfully I really didn’t want to go down that route. Nothing against being an Uber driver - it just didn't feel like the right fit for me.
I realized I was good at tech, apps, puzzles, logic, and systems, basically my skill set from my previous work, and started to wonder how I could do that on my own. I was thinking about the gig economy, found sites like Upwork, where you can sell your skills and people are looking for help so I thought, "Okay, what can I offer?"
I took a shotgun approach, explored a bunch of options, did a ton of research on different jobs, and at the same time, became interested in the whole no-code trend that was emerging in software and apps. In my past roles, I had worked on projects related to automation - even though I didn't think of it that way at the time - and I really like building systems that focused on automation, connecting the dots, and optimizing operations…
And really, I kind of knew there was a market for this sort of work - people are going to keep using apps like these, especially small businesses. And honestly, given my background, I'm much more tech-savvy than the average small business owner, so I figured they might need help with these tasks.
I started to notice that there were plenty of job postings on Upwork related to no-code, low-code, Google Sheets, Excel, apps, and automation – and even better, there were enough jobs willing to pay a decent price.
So I intentionally entered the market with the approach of being both really good and affordable.
The first project is always the toughest, followed by the first five, then ten, and so on. Once you get the ball rolling, it becomes easier for the system to help sell you to other clients, right?
So I just hustled, you know?
On transitioning from side hustle to full-time business…
Putting something out there always comes with a bit of fear:
Will it click?
Will it resonate?
Is it going to have some longevity?
I didn't feel it needed to be a brand for 20 years, but I needed it to be good enough for the next five years or so, and then I can always reposition if necessary.
And my thinking was, if I could manage a job a day, it should be enough to get by.
I knew it would take time to climb that new mountain, but little by little, I started building a website and establishing a social media presence. A lot of this was before I adopted the true Automation Ace branding you see now; I was already making money before I officially launched the brand, so I really backfilled some of that stuff…
And simultaneously with automation, I found my way into Zapier who aimed to democratize connecting apps, integrations, and automation. I thought, "Well, that's an app in itself that I can learn." I already had a solid grasp of coding concepts, programming, HTML, databases, and so on. So, I took a two-pronged approach, doing the Upwork stuff while also aiming to become a Certified Zapier Expert.
I came across a few people on LinkedIn and Twitter who were essentially doing what I'm doing now, so, I started modelling some of my habits and approaches after them, trying to figure out how I could follow in their footsteps, and hopefully, at some point, carve my own niche within this field. I updated my LinkedIn and figured out how to get social proof…
And one of my shortcuts, really, was joining the Zapier Community - where I began answering a bunch of questions to help other users. I wanted to understand what people needed help with, which apps they were using, what questions they had, and the workflows they were trying to solve. I aimed to spot common trends and find signals through the noise. I am pretty good at learning new apps and systems quickly, so if someone had a question, I'd do the research.
A lot of it, honestly, is that I'm just really good at Googling; I know how to find answers.
And eventually, I started seeing some traction. There were consistent job postings that fit my criteria, even if I wasn't winning them. I saw that the types of apps and price points people were willing to pay made it viable if I could reach certain targets.
Sometimes reaching those levels just takes time, and I knew that it would come with time.
So, I hustled.
I don’t know - maybe there was a way to fast track to certain levels that I was missing, but I just figured, as long as I had extra hours in my day that weren't being utilized, and I had the capacity for more work I could keep going.
Little by little, I started taking on more jobs.
From there, if I raised my rates just $10 at a time, it meant I could earn more while still working the same amount or, hopefully, charging more while working less and still meeting my financial goals. And eventually, I realized while I could probably make more money with a startup gig or other opportunities, the trade-off was freedom.
Right now, I have lifestyle freedom.
Today, for instance, I wanted to go to the beach, get in the water, and surf.
It's a Thursday, and that was my lunch break.
My clients didn't know, and they don't care; I managed to get some work done before our interview. *laughs*
I work the hours I want to work. I have the flexibility to work from anywhere in the world at any time. I purposely built these aspects into my life, so if I want to have a long weekend, I can do that; I just bring my laptop.
And I’ve reached the point where I don’t need to take on a job if I don’t want to - I say no quite a bit, and I'm grateful I can do that now.
I don't have to accept projects just to get by; I can be selective. I can choose my own challenges.
On launching the brand…
I've always considered myself a bit of a split-brain person. I'm analytical and technical, but I also have a strong creative side, that I really just haven’t really pursued as much in my career. I enjoy coming up with names, and being creative in that sense. So, when I started thinking about how to brand myself, it involved a lot of market research, and the basics - just checking which Twitter handles, domains, and Instagram handles were available.
I had to consider things like my logo, colors, and overall branding. I wanted something unique and memorable. Automation Ace has the AA in it, which can be advantageous if listings are alphabetical. It might not seem like a big deal, but I think little details like that could work in your favor. I also wanted a name that was comprised of plain English words. I'm a fan of alliteration, which is how I ended up with Automation Ace. I wanted to include "automation" or something related because people often search for how to automate things or integrate them.
I aimed for terms that would be SEO-friendly.
The visual aspect was important; I wanted something that would be distinctive yet convey the concept. An ace, like an Ace card, symbolizes having an upper hand, which adds a subtle layer to the brand. It's all about creating that memorable first impression and making it click with people when they see your brand. A lot of thought went into it, and there was some experimentation behind the scenes before I officially adopted the name.
So, ‘the agency’ is Automation Ace now, but it's really just me. People might perceive it as something bigger, but it's just me.
On remaining a one-man business…
It has been a deliberate choice to remain a one-man shop, at least up to this point. I've explored and dabbled with the idea of scaling, but I'm aware of the limitations. I can only scale so much; I'd have to charge a lot, manage people, or venture into building my own app and scaling it, which comes with a very high chance of failure.
For me, I have a direct correlation of my time or an hourly rate to the money I earn for each project I take on. I may not always work on an hourly rate; I can offer a fixed price for a project based on my estimation of how much time it will take. But to start making money quickly, it was as simple as trading my time for solving someone's problem and getting paid in return.
It's a transaction where I provide a service to clients in need…
The more of these transactions I can do, and if some clients require similar solutions, I can repurpose code and reuse what I've already solved. Over time, I've become more efficient at isolating the jobs I want to take on, then applying them again as solutions to future clients with similar needs come up.
The amount of effort required goes down, so the amount of work I can take on increases, without any additional stress.
It's interesting because the work I do is manual, but the end result is automation. It's a bit of a paradox - I can't fully automate my own work because it involves what's inside my head. That's what sets me apart and partly why I haven't turned to a full agency model. Managing people, handling payroll, reviewing their work, and communicating with clients can often take longer than just doing the task myself in less time…
So, in some ways, I am both my biggest strength and weakness.
On leveraging social proof from Upwork…
I was fortunate - in the right place at the right time even before COVID hit. I was already working from home, doing remote work, and helping businesses lower their overhead and streamline their operations. So when COVID hit, and people needed to transition to working from home, I was already providing those services and filling a niche.
People realized they needed to adapt, and that actually accelerated my business.
It helped me gather more ratings, rankings, and reviews, which are essential forms of social proof. When someone goes on Upwork and sees that I've bid on a job, they can check my profile, see that I've completed many jobs, accumulated many hours, and earned a certain amount of money. This sets me apart from other random newcomers or occasional freelancers. I make it clear that this is what I do full-time.
Additionally, I can point to my Zapier Expert certification and my active participation in the Zapier Community. I've answered thousands of questions and replied to tens of thousands of discussions, helping people solve their problems. While I'm not getting paid for this, I believe that giving away free advice will come back to me in various ways. So, beyond just showcasing my website, I can direct people to these other credentials, which reinforce my expertise.
Anybody can put whatever you want on your website, but when it's someone else leaving you reviews and you're getting ratings and have great rankings that sells itself.
So I've been fortunate enough to hustle hard and am at the point where nobody cares if it’s 50 reviews or 500 reviews - it's just enough. And these are genuine reviews from my real people clients. I've managed to establish that credibility, and even when I go and look at them, I can confidently say that I've put in the work.
You know, I'm active on the internet, and if you want to understand how I think or see the real me, you can check out my profile. I'm not trying to be a traditional business person; I aim to help people become more productive, efficient, streamlined, and optimized—all those buzzwords.
Being a tech person, I can assist with that.
So, I no longer have to constantly bid on projects - the inbound pipeline is more manageable. And over time, I've raised my rates, which serves to screen out clients I don't want to work with and plays into the psychology of perceived value.
You know the saying, you can be two of three things in business - good, fast, or cheap…
I’m good and fast, but I’m not cheap. *laughs*
On Upwork vs. off-platform business…
I don't know the exact split, but if we were to break it down, it has shifted over the years from 80/20 to 30/70 in terms of the money I make on Upwork versus the money I make outside the platform directly.
Upwork takes 10% of my profit, so I’m fortunate now, through referrals and inbound, I'm able to do more direct jobs at this point in time and sending a Stripe invoice costs much less when you’re working at the volume I am.
The numbers you see on Upwork tell part of the story, but not the full story.
It's not a 5% versus 95% situation; it falls somewhere in between. The averaged out numbers across the years would probably be 50/50. But, I'm gradually moving more toward direct work because that's ultimately more profitable for me.
At this point, I have a consistent flow of people reaching out, and some are repeat clients I've worked with for years. There's a lot of trust in these relationships, and we don't have to go through the dance of sharing logins and all that; it's just smooth.
I've grown alongside them, and they've grown with me. And it’s fun to see their businesses thrive, knowing that behind the scenes, I'm like the Wizard of Oz helping to make it all run smoothly.
Present day challenges & finding work life balance…
I'm not great at setting my own personal boundaries, recognizing when I should stop working and step outside. I've even set up reminders for myself, like, "The sun's setting in 30 minutes, go take an hour off…get outside…”
It's nice that I am usually working async, with nearly zero client meetings, and can postpone tasks if need be, but on the flip-side I need to actually force myself to stop sometimes because I can feel the need to always be working…
I still find balancing tough though, I'm constantly glued to my work…
I'm always checking my emails,
my Slack notifications,
bidding on new jobs…
I need to keep that pipeline moving.
Naturally, there are certain weeks of the year that get busier, like the end and beginning of the month, and around holidays, but it can be a bit unpredictable when things slow down or pick up, so at times I wish I had known this was going to be a slow week so I could have planned to travel.
And the big question of course is how do I get more passive revenue in some sense?
I've got a couple little systems, referral links, affiliate links, selling excess leads to my colleagues - I’m not going to retire 10 years early because of any of that, but it’s pretty much found money.
So to expand on that I keep wondering - do I build out courses, things like that?
But none of those are sure bets… me trading time for money is a sure bet at this point.
It's maybe not always sustainable…
If I want to travel this week, great - I can go do that, but I'm not making any money this week.
My main goal is to have three-day weekends every weekend, so I try to front-load my work week and minimize working on Fridays.
On setting revenue targets…
Yeah, I mean, I'm never going to be satisfied - there's always more money to be made in some sense, right?
But I think for me it's really just the question of covering the bills and supporting my lifestyle. I'm a pretty lean sort of person when it comes to my expenses but yeah, I want to be making more money…
I always want to be pushing myself but the ways I can increase revenue are still tied to how much I can work.
So the questions are really, can I raise my rates, can I get more clients on subscription support services I provide, can I continue to convert small clients with an increase in the scope of work.
What do you wish you knew 5 years ago?
Yeah, I mean, I'm definitely happy I bet on myself back then.
You have to be that self-motivated person who gets up every day, opens the laptop, and gets after it. There are days when I'm waiting on a client for two days to reply to something, and all I needed was a simple yes or no to complete their project. But looking back, if I had known better I probably would have said, "Have a plan before you quit your regular job." *laughs*
I could have moonlighted and tested some of this stuff to see if there was a market for it…
I could have built up some business before taking the leap…
But who knows - if I hadn't been in that back-against-the-wall, "I've got to figure this out" mentality, maybe I would have never made the leap.
So, the old me would have said, "Just do it. Go for it, believe in yourself."
Obviously, I had tons of imposter syndrome and doubt - wondering if I was making the wrong choice or wasting opportunities to make good money where I was at in my career. I was trying to figure out what I really wanted to do, the soul-searching side of it. But ultimately, at this point, I'm a much happier person with my lifestyle, the work I do, and the clients I help.
It's much more fulfilling than the previous sense of corporate gratification mindset I had.
How to stay level headed…
Early on, while trying to meet the bare minimum just to get by every month, I had doubts about sustainability. I wondered if I was just going paycheck to paycheck, which was something new for me. However, with experience, I've come to realize that things tend to work out.
It's crazy - last week was slow, but come Monday morning, two clients reached out who needed substantial work. Through ups and downs, I've learned that they come and go and when you look at the bigger picture, things tend to even out.
Trusting the process, having confidence in the systems, and believing in myself is crucial.
On quitting…
At this point, it's challenging for me to even think about going back to working a job - whether it's in an office or remote, where I have to deal with all those people - so there's that.
I'm at a stage where - maybe if certain life events happen - my mentality might shift as well, but right now, I can clearly see the difference between my work life and personal life.
I do job searches quarterly, just to see what's out there - you never know…
And sometimes recruiters reach out with a job opportunity that might have suited me three job titles ago, but I appreciate the connection regardless.
So, I've never completely closed the door.
There have been moments when I thought maybe I've plateaued, but I've witnessed enough consistent growth in my business, especially with AI developments happening that I can’t really see going back. We're bound to see significant changes, and I believe I'm well ahead of the curve in that regard.
Thoughts on improving the business…
Yeah, I'm never complacent with where I'm at.
There's always more for me to learn - that's just how I am.
How can I get better at what I do?
This past year has been all about AI, but even today, a client might say, "can this happen?" and I have to go find the answer, so I’m always learning on the fly in general.
I don't necessarily have aspirations at this point to turn myself into an agency, but if I were to consider the next logical step, it might involve farming out more work or hiring people and scaling up in some way.
I don't have grand illusions of growing a hundred million-dollar company.
Sure, everyone wants that, but I've worked in the startup world and understand how luck plays a role alongside hard work and positioning.
My former company’s co-founders were super savvy entrepreneurs and businessmen, and were able to scale it to a sale. It wasn’t their first rodeo…
But with that, comes a lot of uncertainty - even if you've built and sold stuff before, your second time around doesn't guarantee the same success as the first. We often see these amazing stories in the news about startups like WeWork going from zero to overnight success, but that's not the reality for most.
I think it’s easy to become accustomed to seeing the spam out there that's on social media - these Rags to Riches overnight stories where everything turned out perfect and was easy, or if you take this one little course and it's magic and you will have unlocked the secrets to success. We know that's not reality but that's what gets pumped up and pushed and glamorized.
I'm striving for good, consistent levels of growth where it's less work and easy to scale, within reason. Obviously, if I can make a lot more money, I want to, but not at the cost of bending over backwards or compromising my values - so I have to continue to optimize my operations.
If I can do something more efficiently and save time, that saved time might be more valuable than making an extra dollar.
For now, I have this "company of one" mentality, but life changes may require me to pivot in the future.
That’s it for issue this issue!
To learn more about Troy check him out on LinkedIn!
Read past issues here:
If you, or someone you know would like to be featured, or just want to connect, feel free to message me on LinkedIn!
Thank you for the opportunity to share about Automation Ace!