Sydney de Arenas Sherman is the CEO of two businesses and has founded 6 in her short 10-year career as an entrepreneur. Today she manages The Hive which provides the dynamic team a small business needs to thrive, The Etho, an online marketplace connecting conscious consumers with ethical brands and artisans. She also participates in managing Etho Interiors with her partner and mother, Terrell Sherman, and Ítaca with her life and business partner, Santiago Arenas, which is a Guatemalan-based hospitality brand with 4 restaurants and two hostels. She is also an active investor through The Helm, investing in women-owned businesses making an impact around the world.
Sydney has been published in countless articles, has spoken at conferences on ethical fashion and consumption, and has been featured on several podcasts, including her own, Swearing By it. She is active in any community she is a part of, having mentored young girls interested in a technology career in Austin, TX, human trafficking survivors who want to start businesses in NYC, supports over 15 students with her family in Africa, and donates to animal welfare projects in several places around the world. She has traveled to over 40 countries and currently resides on the base of a volcano in Guatemala with her husband and two children.
What is your typical day, and how do you make it productive?
My typical day is anchored by structure, flexibility, and intention. I work from home and have two young children, so I’ve had to become hyper-focused on how I use my time. Mornings are for deep work — I work from about 8:15 AM to 1:00 PM while our nanny is with the kids. This is when I tackle strategic projects, writing, sales, or team direction depending on the day’s theme (each weekday has a theme like Finance & Growth, Creative & Writing, etc.).
After 1:00 PM, I’m off — with my phone on Do Not Disturb — and fully present with my family. Afternoons are spent at the market, making lunch, walking, playing, or doing bedtime routines. A few nights a week (Monday-Thursday) and then Saturday morning, I get back online after bedtime or while they’re at an activity to finish priority tasks or follow inspiration when it strikes.
The key to making it productive is time blocking combined with radical prioritization. I plan everything on Fridays and Mondays, the what, the when, and the why. If it’s not blocked on my calendar, it probably won’t happen. If I don’t spend time prioritizing, all of my businesses would be flailing instead of thriving. This system makes it possible to manage multiple businesses in 4–5 hours a day, while still being the primary caregiver for my kids.
How do you bring ideas to life?
This is one of the few things I truly excel at—I get started. That’s my trick. I don’t wait for perfect conditions, a flawless plan, or all the answers. I take action. Sometimes that means a bold move; other times, it’s a small, scrappy first step. But either way, I start.
I’m a big believer in running fast, low-cost experiments. I test the idea in real life as soon as possible—whether that’s creating a rough prototype, making a sale before I build the product, or launching with what I have and refining as I go. I believe clarity comes through motion, not thinking. (Of course, there may be outliers, but I have started and run businesses across multiple industries, and this hasn’t failed me yet.)
Perfection is the enemy of momentum. I’d rather learn quickly, pivot if needed, and gather feedback early than spend months planning something that might not work. Most of my businesses started this way: one small bet, followed by another, until it became something real.
What’s one trend that excites you?
More women starting businesses and doing it on their own terms.
I’ve been an entrepreneur for over a decade, and it’s been incredible to watch the shift: more women are stepping into leadership, building companies that reflect their values, and redefining success in a way that includes freedom, family, and flexibility—not just hustle and profit.
What excites me most is that it’s no longer about fitting into the old mold. Women are building businesses around their lives instead of squeezing their lives into their businesses. They’re creating new models, sharing transparently, supporting each other, and proving that you don’t have to choose between ambition and motherhood, impact and income, or creativity and systems.
It’s not just a trend, it’s a movement. And I’m here for it.
What is one habit that helps you be productive?
Weekly planning. Every Friday, I sit down to map out my entire upcoming week: what each business needs, what my top priorities are, and where my time needs to go. Then on Monday, I review it, block my calendar, and adjust for anything that shifted. I even build in an extra hour each day for unexpected fires — because in business, they always happen.
This habit keeps me out of reactive mode and helps me stay focused on what truly moves the needle, rather than bouncing from task to task. I always try to be one step ahead instead of one step behind, but also give myself grace when the system fails. My work is meant to support my life, not the other way around so when life comes knocking I try to be patient and flexible.
What advice would you give your younger self?
Spend every dollar like it’s your last (while believing it will never stop coming).
In the early days of entrepreneurship, it’s easy to get caught up in the excitement—hiring too fast, overspending on tools, or investing in things that feel important but don’t actually move the business forward. I made those mistakes. I didn’t always track ROI, and I assumed more revenue meant more room to spend.
But cash is oxygen for a business, especially in the beginning. I’d tell my younger self to be ruthlessly intentional with every expense, to ask, “Is this helping me grow, or just helping me feel busy?” The most successful seasons of my business have been the ones where we stretched every dollar, made lean decisions, and focused on scrappy, high-impact actions.
Frugality isn’t about scarcity, it’s about freedom and future.
Tell us something you believe almost nobody agrees with you.
I believe you can build a successful, multi-business empire working part-time, even while raising babies, if you have the right systems, boundaries, and mindset.
Most people think that to grow something big, you have to work around the clock and sacrifice everything else. And yes, there are seasons where it’s intense, where the hours are long, and where things fall apart. I’ve lived through those.
But I also believe that once you put the right structure in place, learn how to radically prioritize, and stop trying to do it all yourself, you can absolutely run multiple companies in 4 to 5 hours a day and still be the primary caregiver at home. That’s not a fantasy. That’s my reality.
It’s not easy. It requires discipline, resilience, and letting go of perfection. But it is possible. And I’ll keep building proof of that until more people believe it, too.
What is the one thing you repeatedly do and recommend everyone else do?
Review your numbers. Every. Single. Week.
It’s not glamorous, but it’s powerful. I look at revenue, expenses, margins, and team capacity across all businesses. This rhythm has helped me catch problems early, improve profitability, and avoid burnout from hiring too late.
Once, after reorganizing our team structure, these reviews revealed we were overspending in areas where more affordable systems could be used. Fixing that gave us breathing room and helped us scale in a healthier way. I do this weekly on Tuesdays (businesses) and Fridays (personal) to ensure that I always have a pulse on the numbers and can prioritize what I spend my time on from there.
When you feel overwhelmed or unfocused, what do you do?
I pause and ask myself:
“What will actually move the business forward — or break it — this week?”
This cuts through the noise fast. I use the Eisenhower Matrix (Urgent/Important framework) to triage everything, then I simplify: I either delegate it, defer it, or delete it entirely. I’ve learned that trying to do everything, especially during chaotic weeks, just slows you down.
When we had a literal fire at one of our hostels, I put up an away message and ignored emails for a week. Because in that moment, the business — and my family — needed me in a different way. That clarity comes from having systems in place to fall back on when the unexpected hits.
What is one strategy that has helped you grow your business or advance in your career?
Delegation through systems.
When my business partners joined, we grew the businesses by focusing only on the things we could do, building processes for everything else. We’ve automated our sales flow, built detailed SOPs and training manuals, and created reusable templates for client work. I even used AI to help turn my team’s feedback into documented processes.
When we bought Northwestern Millwork, a door and window business, we built an entire bilingual training manual in 30 days. That made it possible to run the company efficiently while learning a brand new industry, and it continues to save us hours of onboarding time. The more you document and delegate, the more you can grow without burning out.
The real secret is: know your weaknesses and build around them, whether through teams or systems, but it always starts with you.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
One of my biggest failures was merging The Etho, a social impact marketplace I had built from the ground up, with another similar business. On paper, it looked like a smart move. In reality, it was a costly mistake that ended in losing the company altogether.
I had raised $1.25M, built a team, recruited 200+ sellers, and poured myself into its mission. However, the merger created misalignment, and when the pandemic struck, we were unable to recover. It was heartbreaking and financially devastating.
But it taught me everything about leadership, resilience, and what to look for in a partner. I went back to my original business, The Hive, and rebuilt from the ground up—this time more focused, more intentional, and much more protective of my values.
I also used what I learned to start multiple other ventures, including hospitality and interior design companies, and this time, I built them on stronger foundations and with much more aligned partnerships.
That failure shaped the entrepreneur I am today—and I wouldn’t trade the lesson.
What is one business idea you’re willing to give away to our readers?
Sustainable, healthy grocery stores in food deserts.
There’s a huge opportunity to build small-format grocery stores that bring affordable, fresh, and nutritious food to communities that lack access, especially when paired with smart logistics, community partnerships, and local sourcing. Most food deserts aren’t underserved because there’s no demand. They’re underserved because the traditional grocery store model doesn’t work there.
This could look like mobile markets, bulk-buy co-ops, or brick-and-mortar stores that stock local produce and pantry staples with a focus on nutrition and dignity, not just convenience. With the right operations model, government and nonprofit collaboration, and a human-centered approach, this could be profitable and deeply impactful. I’d love to see more entrepreneurs take this on.
What is one piece of software that helps you be productive? How do you use it?
ChatGPT — for everything I possibly can.
I use it daily to save time, clarify my thoughts, and get things done faster. Whether I’m drafting content, brainstorming names, refining messy notes into polished writing, creating SOPs, or navigating a tough business decision, ChatGPT helps me move from idea to execution quickly. It’s not revolutionary, but it has saved me hours each day, and although I use other tools, I keep going back to this one. The next one I am excited about is Ava, a tool to help working parents better manage their care workload.
What is the best $100 you recently spent?
Sometimes I feel guilty asking for help, but the truth is that managing multiple businesses is exhausting, and raising toddlers is even more so. If I can spend $100 to have someone take a few hours of errands, groceries, or household tasks off my plate, that is absolute gold for me right now.
That small investment frees up mental space and gives me a little more room to rest, be present with my kids, or focus on higher-impact work. It’s not about luxury. It’s about survival, sustainability, and choosing support when I need it most.
Do you have a favorite book or podcast from which you’ve received much value?
This particular episode was mind-blowing. I learned about why 60% of girls drop out of sports when they hit puberty, what happens during menopause, and why I need to manage my blood sugar better. I can’t be successful if I don’t take care of myself and with the very limited time I have to dedicate to my health right now, I need quick hit, high impact moves and this was full of information we should all know.
What’s a movie or series you recently enjoyed and why?
I have too many businesses and toddlers to digest anything impressive right now. What I end up going to are murder mysteries or sexy beach reads (all in audiobook format) to give my brain a break from thinking too hard.
Key learnings:
I have worked very hard to get here and I haven’t done it alone. Sometimes I feel like my life looks easy on the outside but it took and still takes daily sacrifices. Knowing myself and continuing to get to know myself has made all of the difference. If you aren’t sure where to look, start with looking at yourself inside, out and eventually you will find the answer you are looking for.