We sat down with Eryn Peters, Co-Creator of the AI Maturity Index, Startup Advisor, and Future of Work Evangelist, to explore her journey of crafting a purpose-driven career. With a passion for innovation and a knack for navigating the evolving landscape of work, Eryn shares her insights on leveraging sweat equity to build meaningful ventures beyond the traditional 9-to-5.

From Cubicles to the Digital Frontier

Ever felt stuck in an office, wondering if there’s a better way to work? That was Eryn Peters’ reality. After a brief stint in an office job, she realised that traditional office life wasn’t for her.

“I remember seeing a meme that said, ‘The early bird gets to cry in the parking lot for an extra 15 minutes.’ I was sitting in my car, thinking, ‘This is too real.’” That moment marked a turning point. She quit her job, sold her house, and booked a one-way ticket to Uruguay. "I thought, I'm hireable; I'll get a fully remote job, which I did.”

More professionals are leaving behind rigid 9-to-5 routines, seeking roles where their skills create lasting impact. Sweat equity provides a way to align work with personal values, blending professional growth with meaningful contributions.

A Life of Remote Work and Flexibility

"I’ve had a very non-traditional career path, which is probably why I’m so open to working for a mix of equity and capital," Eryn explained.

Eryn’s journey into remote work started early. At 19, while attending Red River College in Canada, she juggled classes with a remote marketing role for a Toronto-based company. “It was when Facebook was just taking off, and everyone at my business school said, ‘This is a fad, and nobody's going to use it.’ I thought they were wrong.” 

Eryn dropped out of her course and enrolled in a college where she was able to work full time while continuing her studies. This decision laid the foundation for a career built on flexibility, self-direction and an openness to opportunities beyond traditional 9-to-5.

Discovering Sweat Equity: Risks and Rewards

Eryn’s first encounters with sweat equity began when she joined Toptal, a company that connects developers in emerging markets with clients in the U.S. and Europe. Working closely with Toptal’s startup clients  gave her insight into the mechanics of sweat equity agreements, a staple in early-stage ventures. “It was my first real taste of how startups leverage equity deals as their matches through Toptal were often their first paid hires. It opened my eyes to both the potential rewards and the risks of betting on an idea.”

Her experiences underscored the importance of setting clear boundaries and building trust. In these arrangements, a simple handshake won’t suffice - transparent contracts, complete with vesting schedules and milestones, are essential to protect everyone involved.

Negotiating Sweat Equity: A Science, Not an Art

Eryn approaches equity negotiations with precision. “It’s more science than art. There are industry benchmarks for advisors—based on time commitment and the activities involved.”

She breaks the process into three key steps:

1. Understand Your Market Value: Research the market rate for your expertise. “There are benchmarks online for advisors, which are based on how much time you're going to give and what types of activities you'll do. I have written a freelance pricing guide that talks about time, milestones, retainers, and more.”
2. Know the Company’s Pre-Money Valuation: Use financial forecasts or valuation tools to avoid guesswork. A clear sense of the company’s worth ensures fair negotiations. Avoid the pitfall of someone valuing their company for the next stage rather than where they’re currently at.
3. Craft Precise Terms: Implement vesting schedules, cliffs, and milestones to ensure equity is earned over time or linked to results. Don’t feel obligated to stick to any one set of terms - choose what works best for all parties.

Eryn also advocates for hybrid models. “You can stack compensation. For example, equity plus success-based bonuses. “If I help deliver a major campaign, I get a commission on sales along with equity.” With AI tools driving efficiency, she sees the shift from time-based pricing to value-based models as a natural fit for equity deals.

Red Flags to Watch For in Sweat Equity Deals

Eryn has learned to spot inconsistencies and vague terms through experience. “One time, I proposed an equity deal, but the contract listed share options instead, which is a big difference.” She stresses the importance of clarity - equity grants ownership, while share options only offer the right to purchase shares later. “It’s essential to ensure everyone’s speaking the same language from the start.”

A lack of financial transparency is another red flag. “If the company can’t provide key details, like the number of shares or strike prices, you’re going in blind.”

Partnership behaviour also matters. “Are they respectful of your time? Do they communicate when they’re running late? These small things matter because you’re betting on each other. If someone’s evading questions about roles, responsibilities, or exit strategies, that’s also a red flag.”

Eryn recalled one example: “If one person plans to run the company forever without a liquidity event, that’s important to know. You need to understand these dynamics before committing.” 

Evolving Her Approach to Sweat Equity

Working with startups in the marketing, HR & staffing sectors, Eryn focuses on helping founders unlock growth opportunities. 

Over time, Eryn has refined her strategy. “I no longer take equity-only deals,” she explained. “Even a nominal payment ensures both parties have skin in the game. It transforms the relationship from a leap of faith into a real partnership.”

When deciding whether to invest her time and skills in a project, Eryn prioritises two key factors: people and purpose. “Do I like spending time with these people? Are we building something impactful? If I am giving my time, I want it to matter.” 

Balancing Risk with Freedom

Eryn is candid about the risks of sweat equity, acknowledging that her personal circumstances make it easier to take chances. “The worst-case scenario? I downsize, move somewhere less central, and it’s just me and my dog. I’m aware that my situation makes risk more manageable- I don’t have dependents or fixed ties.”

She is also transparent about the role of privilege. “I know that being a white woman born in Canada gives me opportunities others might not have. If things fall through, I have options. Many people don’t have that safety net.”

Balancing Risk with Optimism

For Eryn, success in sweat equity requires balancing realism with optimism.

We catastrophize by nature - it’s a survival instinct. But with equity, you need to flip that and think, ‘What if it all works out?

She believes sweat equity calls for an adventurer’s spirit. “It’s a gamble. You have to believe in the possibility of winning the jackpot, even if the odds are long.”  

When evaluating sweat equity, Eryn considers three dimensions of risk:

1. Personal Risk: Can I handle it if it doesn’t work out?
2. Opportunity Risk: Does this company have what it takes to succeed?
3. External Risk: Are there outside factors - like a pandemic or geopolitical issues that could derail things?

Eryn’s Key Takeaways for Sweat Equity Success

• Contracts Matter: Always have a written agreement detailing roles, responsibilities, and equity terms.
• Consider hybrid models: Avoid equity-only deals unless compensation is clearly structured. Even small payments signal commitment on both sides.
• Choose Projects Wisely: Collaborate with people you trust and align with projects that inspire you. Purpose drives sustainable motivation.
• Negotiate Like a Pro: Use research, valuation tools, and structured agreements to approach sweat equity negotiations logically.
• Watch for Red Flags: Stay alert to unclear contracts, lack of transparency, and unrealistic expectations.
• Know Your Risk Appetite: Understand your financial and emotional capacity for risk before committing to a sweat equity role.

Looking Ahead: A Model for the Future

Eryn’s story demonstrates that the future of work extends far beyond office walls. It’s about finding ways to contribute meaningfully, whether through remote work, sweat equity, or advisory roles. Sweat equity, she believes, is more than just shares. “At the end of the day, it’s about building something meaningful with people you respect. That’s where the real magic happens.”

 

Do you have a Sweat Equity story to share?

Email Mickela to join our Sweat Equity Stories series, where we spotlight the journeys, challenges, and successes of those navigating this path. We’d love to feature your experience!

Wondering how to value your time in a sweat equity deal? Explore how to set your freelance rates with Eryn's Freelance Price Guide.

For more insights, read about Mickela Sonola's transformative Sweat Equity Journey - Trading Talent for Equity.