How a risk-averse founder hit $500k/yr while playing it safe

Marissa Goldberg played it safe, side hustling until her business, Remote Work Prep, replaced her high-paying tech exec salary. Then, she slowly transitioned out of her position while maintaining her safety nets.

Her risk-averse approach worked. Her best year to date brought in $500k — for a team of one.

Here's Marissa on how she did it. 👇

"Coopertition"

My career in tech started early. At 12, I began competing in international robotics competitions, which introduced me to the concept of “coopertition”. This is where I first got the taste of collaborating with people all over the world. I instantly fell in love with working across boundaries to solve complex problems.

In 2015, I started working remotely full time as a dev. I loved how much autonomy and freedom it gave me, and I quickly got promoted into leadership because I was being judged by the quality of my work rather than how young I looked.

One of my favorite things about remote work is the shift in judgement. Instead of being judged on external factors (like how you dress and networking skills), you are judged on your output. As someone who loves to learn and take initiative, this shift made my career take off like a rocket ship.

Fractional ops

In 2018, I founded Remote Work Prep to help fast-growing remote teams solve the unique challenges of distributed work. I started it on the side to help other remote managers who had requested it.

It was never supposed to be a full-time thing. And I grew up poor, so I took a conservative approach to building a business.

I went full time on it in 2021 after my company offered “entrepreneurial leave”. I committed to going back to PM life once my take-home pay dropped below my tech exec income. It never did.

I specialize in helping fast-growing remote companies (e.g. startups, agencies, creator teams) get rid of meetings so they could focus on real work.

I offered:

• Fractional operational services (COO/Chief of Staff) for fast-growing remote companies, including YC-backed startups, agencies, and creator businesses (e.g. YouTubers like Thomas Frank). This is my primary revenue driver.

• Courses such as Mastering Remote Leadership, Avoiding Burnout from Remote Work, and The Async Way to train hundreds of remote workers in future-of-work skills.

• The Remotely Interesting newsletter to explore how to revolutionize how you live by changing how you work.

More recently, I launched the Work Forward Society, a community for forward-thinking remote leaders who want to tackle meeting fatigue, build team autonomy, and embrace innovative workflows. It’s currently in beta, and my focus is on growing it into a thriving space for leaders to learn, share, and experiment with better ways of working.

When I was starting out, I was frustrated by the lack of transparency around pricing in service-based businesses. So here are some of my rates for reference: 

• Productized service for setting up brand-new remote teams, starting at $50,000

• Fractional ops services (COO/Chief of Staff), starting at $10,000/month

• Leadership coaching, priced at $500/hour (with package discounts)

While I’ve considered creating a software product (especially during the early pandemic when I received a lot of inbound interest from VCs), I decided against it. The market is already saturated with tools, and the bigger issue isn’t the lack of tools; it’s the lack of knowledge on how to put it all together to create an effective virtual environment for remote teams.

In my best year —2023 — I scaled my business to about $500k in revenue while working just 30 hours per week. This year, I spent most of the year on maternity leave, so it was much less.

Keeping the safety net

Like I said, even when my company exploded during the pandemic, I still ran it as a side business. I ran it on the side for three years until I officially went full-time (when my side business profits exceeded my tech exec income).

Not relying on the side income allowed me to say no to everything that would make more money but leave me unhappy. As a result, I was able to slowly pivot and sculpt with zero financial pressure. It allowed me to create my dream job.

People usually think of quitting as an abrupt thing. But it doesn't have to be that way. If you want to leave on good terms, leave the door open for future opportunities, or you're interested in a more calm, stable switch, a slow transition might be just for you. 

When my side business became too much to juggle with my full-time job, I switched my job to a 3.5-day workweek. I did a half day on Wednesdays and took Fridays off. I negotiated this shift during a yearly review and was able to do this schedule change while keeping the same pay (instead of getting a raise). This gave me more time to spend on my side business without any financial change.

This solution worked for a while. Then, about six months later, I was reaching the point of officially wanting to go full-time. I was about to run the first cohort of my Mastering Remote Leadership course and knew I needed extra time. So I went to my boss planning to put in my notice, and instead, he offered me a 2-month entrepreneurial leave.

Basically, I'd go on leave for two months, but the position would be waiting for me after that time. This significantly decreased the risk for me because I had time to give my all to my live course while not limiting my future options. Because what if I hated teaching? What if I got bored and didn't like running my business full-time? Instead of having no Plan B, I had a safe option to fall back to.

It's been over a year since I went full time and I'm still extremely happy with my slow transition out. I highly recommend this route to anyone who wants to safely make the switch.

Growing more than revenue

My biggest challenge remains that I hate sales and marketing. Tech and systems thinking have always been my strong skills. Sales and marketing have always felt like talking about the work rather than doing the work, and that drives me crazy.

Taking courses like 30x500 have helped me a lot in this area, but my business is held back a lot from me just not enjoying this side of the business.

Referrals

My approach to growing my business isn’t for everyone. I rely primarily on referrals. I focus on doing great work, delivering results, and building strong relationships. When people are happy, they pass my name along. It’s simple, and it works for me.

Newsletter and interviews

Beyond referrals, people often find me through my newsletter, Remotely Interesting, or from podcast interviews where I share my insights on remote work and leadership. These channels have helped me establish a reputation and reach an audience without relying on aggressive marketing tactics.

Growth based on constraints

When it comes to growth, my chosen constraints guide everything I do:

• Stability: As someone who’s risk-averse, I don’t want my revenue to feel like a roller coaster ride. I prioritize steady, sustainable growth rather than gambling on big changes.

• A life outside of work: I protect my time for family, health, and hobbies. For example, I ran for and was elected to local public office, which wouldn’t have been possible if work consumed all of my energy. This means being intentional about avoiding the “work vacuum” that can take over if you’re not careful.

• Autonomy over more money: For me, the ultimate reward isn’t just a bigger paycheck — it’s spending my time doing work I love with people I respect. That’s why I frequently say no to opportunities that don’t align with my values or goals.

When people talk about growing their businesses, they often focus solely on money. My advice to indie hackers is to take a step back and think about what growth means to you. Maybe it’s more revenue, and that’s great. But maybe it’s flexibility, time with loved ones, or mental clarity.

Growth in one area often comes at a cost in another, so be intentional about what you’re working toward. Make sure the actions you take are creating the life you want, not just chasing what other people say you should want. 

Taking hits

My business has taken hits more than once because of misplaced trust — times when someone committed to something, only to backtrack after I had already made sacrifices on my end. To address this, I’ve implemented safeguards like retainer-for-access contracts, which have helped. But I know there’s more I could be doing to protect myself from these situations.

However, these precautions take time and effort, and they can come at a cost to relationships — a cost I’ve often hesitated to pay. Navigating this balance is tricky, and if you’ve faced something similar, my advice is to approach business with your eyes wide open. Understand the risks you’re taking and the potential fallout.

At the same time, don’t let the inevitable challenges of business harden you or strip away what makes you you. Trust and hope are powerful traits, and while it’s wise to be cautious, it’s just as important not to let the messiness of business change the core of who you are.

A killer tax tip

One tip: Put 50% of your business income aside. This is something I did from the very beginning. Any income that came into my business, I immediately put 50% in a savings account for taxes.

Then, after I run taxes in January/February, I treat the remaining amount as my tax return, and this is what I use as the budget for business expenses for the rest of the year. I pay for all tools, courses, admin fees, etc., from this account. This method requires you to be scrappy in the first year but pays off every year after.

This is how I've been able to have a profitable business from day one. All of my expenses are effectively paid for a year in advance. I end up saving money too, because I can pay upfront for yearly subscriptions at a discount instead of having to choose monthly.

It's also helpful because I've never been left in the red or scrambling at tax time. On the contrary, I actually look forward to tax time because it refreshes my business budget.

You don't have to be a risk taker

Don’t let the "risk-taker" stereotype hold you back. Entrepreneurship is often painted as a daring leap of faith, described as "brave," "gutsy," or "all-in." But if that narrative fills you with dread instead of excitement, know this: You don’t have to be a risk taker to succeed as an entrepreneur.

For years, I avoided launching anything of my own because I thought my risk-averse nature disqualified me from being an entrepreneur. I was wrong. The truth is, entrepreneurship isn’t about risking everything. It’s about building something valuable. It’s about solving problems, creating opportunities, and delivering value in ways that align with your strengths.

If you’re risk-averse like me, approach entrepreneurship with a plan that matches your comfort zone. Start small, test your ideas, and build iteratively. Focus on creating a sustainable foundation rather than chasing "overnight success." You can grow a business without gambling everything, and there’s no shame in taking a measured approach.

You're an entrepreneur because you create valuable things for the world. That’s what matters, not how much risk you take. So if you’re just starting out, give yourself permission to build your business your way.

More specific tips on the topic here.

What's next?

I’m focused on jumpstarting my business following my return from maternity leave. This has been the longest break I’ve ever taken, and it’s been both a challenge and an opportunity to rethink what’s next. My priority is on regaining momentum while keeping the business aligned with the life I want to lead.

Right now, that involves scaling The Work Forward Society, the community I’ve launched for remote leaders who want to reduce meeting fatigue, foster team autonomy, and embrace async workflows.

I aim to maintain a business that grows sustainably. That means keeping expenses lean, prioritizing value-based offerings, and ensuring that my work doesn’t come at the cost of my health, family, or being an interesting human outside of work. Whether it’s scaling a community or exploring new opportunities, my overarching goal is to create the life I want while helping others do the same.

You can follow along at my personal website, X, and Bluesky. Or check out Remote Work Prep, the Work Forward Society, and the Remotely Interesting Newsletter.