Every founder starts somewhere—and often, that beginning comes with a steep learning curve. The early days of building a business are filled with trial and error, discovery, and lessons that shape everything that follows.

In this article, Dreamers & Doers members look back on their journeys and share the insights they wish they had from the start. They also reveal the practical changes that could have made their first year smoother and more efficient. Whether you’re just getting started or already in the thick of it, their lessons offer valuable perspective for navigating the path ahead.

Liane Agbi

Founder of Beautifuli Digital, a boutique web agency that builds high-performing websites for ambitious female founders.

What I wish I knew: Systems and automation aren’t just a nice-to-have. They are the difference between being a burnt-out freelancer and actually being a CEO. Once I stopped doing everything manually and started building processes that worked without me, I got my time back and became a sharper, more strategic leader.

The one thing I'd do differently: Automate my client workflows from day one—from folder creation to onboarding videos to follow-up sequences.

Clara Ma

CEO & Founder of Ask a Chief of Staff, a boutique executive search and career development platform for strategic operators.

What I wish I knew: It's not wrong to support yourself with contractors. Fractional and project-based workers can handle the manual and repeatable work while you focus on what actually moves the needle.

The one thing I'd do differently: Let go of control and delegate far earlier, fully leveraging my executive assistant’s ability to triage my inbox.

Ciara Siegel

Brand & Marketing Strategist and Founder of CJC, bringing the strategy behind billion-dollar brands to small businesses.

What I wish I knew: There are entire communities of founders willing to share what they’ve learned. Once I joined these groups, I realized that almost every challenge I faced had already been navigated by someone else, and their wisdom makes the leap into entrepreneurship less intimidating.

The one thing I'd do differently: Productize my services much earlier. In the beginning, I created custom proposals for every client, which meant constantly reinventing the wheel.

Victoria Alexander

Owner & Principal Broker of Realty Collective LLC, a boutique brokerage in Brooklyn that celebrates the borough's rich history, architecture, culture, and people.

What I wish I knew: Staying small isn't failure. I scaled up to four offices, and then I had to make the painful call to consolidate back down to one. At the time, it felt like going backwards, but I learned I'd rather be smaller and right than bigger and compromised.

The one thing I'd do differently: Build the bones before trying to grow. I thought systems would make the work feel corporate, but they're what let me stay small and intentional without burning out.

Lexie Smith

Founder & CEO of GROWTH MODE Personal Brand Agency, a personal brand agency for leaders & founders.

What I wish I knew: As a founder, your personal brand can become your greatest business asset. Early on, I tried almost everything to avoid building one, even as I was building personal brands for other people.

The one thing I'd do differently: Build my personal brand from day one instead of hiding behind the company name. Trust builds faster when people can connect the work to a real person.

Nicole Leon

Founder of L Leon Virtual Assistance LLC, providing high-level virtual and executive support.

What I wish I knew: There is no reward for burnout. I thought exhaustion meant I was building something meaningful, but it really just meant I was building without boundaries.

The one thing I'd do differently: Build rest into my business model from day one. Protected days off, clearer client boundaries, and realistic capacity planning would have saved me from overcommitting and undercharging.

Ingrid Zapata Read

Founder of MyOrbit, a testimonial and credibility platform for service-based founders.

What I wish I knew: The words of the people you serve are your most powerful marketing asset. I spent years trying to perfect my messaging, when in reality everything I needed to grow was already right in front of me in the feedback, the thank you notes, the DMs, and the conversations I was having after events.

The one thing I'd do differently: Create more structure to avoid unnecessary stress. I was constantly recreating proposals, rewriting messaging, and digging through emails instead of building systems that could support my momentum. If I had built those earlier, I would have saved time, protected my energy, and made scaling much smoother.

Erika Mosteller

Owner of Erika B. Marketing Agency, guiding visionary leaders to use story as their competitive advantage through marketing and print media.

Photo by: Ashlea Snell of The Snells Photography

What I wish I knew: That I would cry. A lot. And feel guilty for exposing my family to risk. But I also wish I had known that I am big enough to contain my vision without fear, and that showing up, putting in the reps, and serving clients the way I want to be served would grow my revenue.

The one thing I'd do differently: When people doubted me or when I doubted myself, I wish I had a list of accomplishments to pull out and review as a tangible reminder that I have big dreams and can make them happen.

Lucy Bedewi

Messaging Strategist and Copywriter at My Write Hand Woman, a messaging and copywriting business for irreverent women founders.

What I wish I knew: That I shouldn’t get attached to offers and ideas. I spent so much of that early business time trying to make my ideas work instead of asking the market how I could shift my ideas to be more attractive to people's actual problems.

The one thing I'd do differently: Done market research every quarter, constantly talking to my current clients and dream clients, then using their feedback to make changes.

Catharine Montgomery

Founder and CEO of Better Together Agency, a Black woman-founded, AI-forward communications agency.

What I wish I knew: VC money comes with strings you cannot always see until it is too late. Investors can say they believe in your mission and still move to take control of the brand you built from scratch the moment the numbers shift.

The one thing I'd do differently: Treated revenue as my primary funding strategy from day one instead of treating investors as the goal. Clients who pay you give you more freedom than investors who own you, and that freedom compounds over time.

Ellen Hockley

Founder of Ellen Hockley Consulting, a business strategist, podcast co-host, and community leader devoted to supporting women building meaningful work on their own terms.

What I wish I knew: Just because you've started a business before doesn't mean you have the skills or capital to start another one in a completely different field—and that's okay. With that, don't be afraid of failure or to take big leaps and see where you fly—or fall.

The one thing I'd do differently: Hired a bookkeeper earlier—but also make sure I understand my finances well enough to know when my bookkeeper was making costly mistakes.

Lisa Friscia

President & Founder of Franca Consulting, a boutique consultancy that helps organizations build the leadership and talent infrastructure that turns strategy and values into how work actually gets done.

What I wish I knew: Just because you see a problem clearly doesn’t mean it’s the problem your customers are prioritizing. Insight alone doesn’t create a business. You have to meet people where their urgency and budget actually are.

The one thing I'd do differently: Spend time earlier doing focused market research—not just on the problems leaders were facing, but how they were prioritizing them and what they were actually willing to invest in.

Emily Dick

Author & Branding Strategist and Designer of Unbuttoned Brands, a bold brand studio helping values-driven service providers stand out without burning out.

What I wish I knew: It often takes two or three years to actually make money because you're figuring out what you love doing, unlearning garbage advice about how you "should" run your business, and experimenting to find what actually works for you.

The one thing I'd do differently: Trust my gut more and stop trying to follow strategies that work for someone else's energy levels and brain.

Amanda Lien

Founder & Full-Stack Content Marketer of Minutiae Content Co, a writing and strategy firm specializing in authentic thought leadership and marketing content.

What I wish I knew: How to qualify a lead earlier. I want to ensure equitable access to my skills, but early on, I didn't understand that the way to do that is by tiered offerings, not by being willing to drop my prices for any and all inquiring parties.

The one thing I'd do differently: Create a system where anyone can access my services at different tiers depending on how much of an investment they're able to offer at that moment in time.

Demi Oloyede

Founder & CEO of Leansite AI, a technology platform modernizing facility operations.

What I wish I knew: A lot of entrepreneurship is really about focus. In the beginning, it’s easy to chase every opportunity, partnership, or feature idea—but real progress comes from solving one problem extremely well.

The one thing I'd do differently: Speak to more customers before building anything. Early on, I thought clarity would come from building the product, but it actually comes from listening deeply to the people experiencing the problem every day.

Peri Finkelstein

Founder & CEO of Team Peri Foundation, driven by justice, compassion, and the belief that true inclusion celebrates diversity.

What I wish I knew: Even with a strong board and capable people in place, the responsibility ultimately stays with the founder and CEO. It’s my company and my name on the line.

The one thing I'd do differently: Register my nonprofit as a public foundation from the start instead of a private one, which I did at the advice of a legal team I hired. I should’ve trusted my gut.

Allison Ullo

Founder of Leaves of Leisure Tea, a luxury low- and no-caffeine tea company.

What I wish I knew: I wish someone had prepared me for the constant cycle of effort and uncertainty: spending hours editing a piece of content that barely gets engagement or investing money in marketing experiments that don’t pay off right away. Those moments can really shake your confidence if you’re not prepared for them.

The one thing I'd do differently: Start with a simpler minimum viable version of my product instead of investing heavily in premium packaging right away, which required a significant upfront investment that put pressure on the business early on.

Jessica Sikora

Founder & Executive Director of SUPERBANDS, a nonprofit transforming the power of music fandom into a force for belonging, resilience, and youth mental wellness.

What I wish I knew: Passion alone isn’t a strategy. When you’re building something mission-driven, you still need clear positioning, strong partnerships, and a sustainable model if you want the impact to scale.

The one thing I'd do differently: Focus earlier on building the right advisory circle instead of trying to figure everything out myself. Having experienced operators, industry connectors, and strategic thinkers around the table accelerated my learning curve dramatically.

Lakeya Cherry

CEO & Founder of Lakeya Cherry LLC, a dynamic executive coaching and consulting business that empowers leaders and organizations to maximize their potential.

What I wish I knew: Joining a business community right away is so important. You gain perspective, support, and practical insight from people who are navigating similar challenges.

The one thing I'd do differently: Invest earlier in support. Even part-time administrative, marketing, or operational help would have made a meaningful difference.

Allison McMillan

Founder & CEO of Tavlin Consulting, taking a human-centered, collaborative approach to help tech and nonprofit leaders transform how their teams work.

What I wish I knew: Everyone talks about the freedom of running your own business—and some days that's exactly what it feels like—but nobody warns you that you're not trading one boss for zero. Some days you're trading one boss for six, and they all have different expectations and timelines.

The one thing I'd do differently: Get into the habit earlier of regularly asking, "Is this moving my business goals, my personal goals, or neither?" before agreeing to new opportunities. This would have helped me track where my time was going so that my yeses were more intentional.

Catalina Parker

Co-Founder of Relatable Nonprofit, helping former nonprofit professionals build consulting businesses.

What I wish I knew: You get clarity by moving. I wish someone had told me to do it scared and stop waiting for permission or the “perfect” moment.

The one thing I'd do differently: Normalize the “maybe I should just go back to a job” spiral as a stress response, not a signal that business wasn’t for me. A simple rule like “no quitting decisions on a bad week” plus a written why and 90-day targets would have saved a lot of time and heartache.

Gabriela Fiorentino

Founder of Nest Earth, a supportive community for eco-conscious parents.

What I wish I knew: Building community is the business. I spent so much energy on the product before realizing that the relationships and trust you cultivate from day one are what actually sustain everything else.

The one thing I'd do differently: Niche down much sooner. I tried to speak to everyone who cared about sustainability, when my real magic was specifically in the intersection of eco-conscious living and parenting. Once I got clear on that, everything clicked into place faster and with far less wasted effort.

Ashley Rector

Founder of Quimby Digital, a social-first marketing agency helping high-growth parenting and women’s health brands scale.

What I wish I knew: How much confidence matters in a room. Yes, you are selling your services, product, business—but more than that, you are selling yourself. Those first few clients are betting on you, so walk into a room like the expert you are.

The one thing I'd do differently: Talk to even more people. Networking is what made me successful in the beginning.

Jasz Joseph

Founder & Digital Strategist of Jasz Rae Digital, helping B2B companies turn their marketing into a revenue engine.

What I wish I knew: Running a business requires spending almost as much time working on the business as working in it. Client work matters, but the real growth comes from activities like selling, building relationships, and thinking strategically about where the business is going.

The one thing I'd do differently: Start hiring specialized subcontractors earlier. Trying to do everything myself kept me stuck in delivery work instead of building the business.

Charmaine Green-Forde

Founder & CEO of Chapter tOO, a data-driven, people-first workplace advisory and coaching practice.

What I wish I knew: Your network isn’t automatically your business network. Many people who valued your insight in a shared workplace environment will still expect access to your expertise informally once you’re running a business, and even the portion of your network that becomes paying clients eventually taps out.

The one thing I'd do differently: Surround myself with other people who are actively building businesses sooner. Once I found those spaces, the learning curve became much easier to navigate.

Natasha Durkins

Founder & CEO of Durkins Strategy Group, providing strategic executive advisory, keynote speaking, and executive coaching.

What I wish I knew: Entrepreneurship requires surrendering the need to control outcomes. The real leverage comes from focusing on how you show up, because that’s what creates the conditions for opportunity.

The one thing I'd do differently: Treat my early offers as experiments instead of permanent decisions. I spent far too much time trying to get the “perfect” program in place, as if launching something meant I was locked into it forever. In reality, you can adjust anytime, and letting real feedback guide your next move accelerates everything.

Vishakha Raghuram

Founder of FYI: Forever YoungIsh, reminding you that living on a timeline is overrated while becoming yourself is the real glow up.

What I wish I knew: How alone I would feel. Building a business starts with a vision only you can truly understand—and not everyone will be on board with it. In the end, that’s what makes the business yours.

The one thing I'd do differently: I wish I hadn’t spent so much time dwelling on the negative.

Ronit Menashe

CEO and Co-Founder of WeNatal, reinventing fertility with the first prenatal system designed for both women and men.

What I wish I knew: The sooner you treat your gut like a credential, the better your business decisions will be. We initially let our insecurities about being new entrepreneurs override what we knew to be true. Whenever we had a bad feeling about a vendor, a partnership, or an agency and chose to ignore it, it cost us.

The one thing I'd do differently: Walk away from the wrong fit sooner. Early on, we hired a web development agency that wasn’t aligned with our vision. We both sensed it immediately but had already invested $10,000, so we gave it another chance. Months of frustrating back and forth later, we launched a beautiful website we had to completely rebuild less than a year later.

Lauren Graham

Founder of Velvet Frame, a bespoke philanthropy advisory for next-generation donors who want to move money with clarity and courage toward systemic change.

What I wish I knew: How many costs a solopreneur absorbs that never show up in the final deliverable. I would have charged more earlier to accurately reflect the strategy, labor, admin, overhead, and all the invisible costs required to do excellent work sustainably.

The one thing I'd do differently: Get much more specific about the exact client I was building for, and only focus on finding and serving that clients. The narrower the focus, the stronger the message—and the easier it became to build momentum.

Fatima Teos

Founder & Co-Founder of Vita Nova Media | NJK Partners, a creative brand studio that helps female founders and mission-driven entrepreneurs show up with clarity, build real trust, and become the obvious choice.

What I wish I knew: Clarity comes from action, not the other way around. In the beginning, I thought I needed a perfect plan before I could show up, sell, or be taken seriously. I've since learned that entrepreneurship is built in motion, through a process of testing, refining, and listening closely to the people you're serving.

The one thing I'd do differently: Simplify my offers and build my systems much earlier, with automation and operational efficiency in mind from the start (including leveraging AI as a tool for systems, repeatable workflows, research, and backend support). I spent too much time on aesthetic, time-consuming tasks that made it harder to manage my time, energy, and tracking well.

Tianna Soto

Keynote Speaker & Journalist of Stories With Heart, LLC, helping people embrace their unique stories, spark creativity, and step confidently into their purpose.

What I wish I knew: I don't have to do everything myself and it's okay to ask for help. Getting support in areas of the business that I'm not as familiar with can be really beneficial in the long run, rather than white-knuckling through it.

The one thing I'd do differently: Seek out a mentor in the field. During my first year of keynote speaking, I felt like I had to be scrappy and figure everything out all on my own, but years later, once I started working with mentors and coaches, my business transformed rapidly for the better.

Ambreen (Amber) Chaudhry

Founder & Pharmacist of Noori Skincare, a science-backed, clean, barrier-focused, skincare line formulated specially for teens and tweens.

What I wish I knew: Growth isn’t linear. There are slow seasons, setbacks, and moments of doubt, and that’s all part of the process. What matters is staying consistent and trusting your vision.

The one thing I'd do differently: Make decisions faster, knowing I could always refine or correct them later instead of trying to get everything perfect the first time. That shift alone would have saved me so much time, money, and unnecessary pressure.

Amanda Northcutt

Founder & CEO of Level Up, helping experienced consultants, coaches, and subject-matter experts build scalable, recurring-revenue businesses.

What I wish I knew: Focus is a superpower. Most opportunities are distractions, and the companies that truly scale are the ones that say no far more often than they say yes.

The one thing I'd do differently: Protect my time more aggressively and focus only on the few activities that directly drive revenue and customer outcomes.

Amanda Hofman

Chief Swag Officer of Go To Market, the anti-boring branded merch and swag experts, changing the way the world handles swag.

What I wish I knew: Everyone is winging it more than it seems. People don’t start out as experts. They build that expertise over time, and it’s completely normal to feel a little out of your depth along the way.

The one thing I'd do differently: Stop comparing myself to what I was seeing on Instagram. What shows up there is a curated version of a business—not the full picture—and it’s easy to misread that as reality. Focusing on my own pace would have saved a lot of unnecessary pressure.

Anjali Purohit

Creative Director & Founder of Studio Variously, a sustainable textile design studio creating artisan scarves, handwoven throws, handmade journals, and ethical gifts.

What I wish I knew: Events build connections, but don’t let them steal time from your business. Networking is valuable, but prep-heavy events can derail focus and productivity.

The one thing I'd do differently: Be more selective about investing my energy where it truly moved the business forward.

Karee Laing

Founder & Chief Brand Strategist of Studio SB Agency, a bespoke brand strategy agency helping established founder-led brands close the gap between who they've become and how their brand shows up in the world.

What I wish I knew: To separate my self-worth from the business. When I struggled, I thought I was the failure.

The one thing I'd do differently: Show up for my own brand with the same rigor I brought to my clients. In my first year, I wrongly told myself that doing great work for clients was enough and that I didn't need to be visible because my results would speak for themselves.

Sydney de Arenas

Founder of The Hive, building and scaling companies that support entrepreneurs, strengthen local economies, and make ethical, sustainable growth more accessible.

What I wish I knew: How much of building a business is actually about managing people, energy, and expectations—not just delivering a great service.

The one thing I'd do differently: Build clear systems and boundaries from day one. This would’ve saved me from over-delivering, undercharging, and constantly putting out fires instead of building something scalable.

Rachel McCollum

Co-Founder of SYS, a modern relationship ecosystem helping exceptional people find and sustain extraordinary love and connection.

What I wish I knew: Building a business is really about building yourself. The inner work you do as a founder shapes the culture, relationships, and opportunities you attract far more than any strategy.

The one thing I'd do differently: Set clearer boundaries around my time and energy much earlier. In the beginning it’s easy to say yes to everything because you want momentum. Focusing only on the right clients and aligned opportunities would have saved me a lot of time and allowed the business to grow more intentionally.

‍All individuals featured in this article are members of Dreamers & Doers, a highly curated community and PR Hype Machine™ amplifying extraordinary women entrepreneurs and leaders through authentic connections, credibility-boosting visibility, and opportunities that accelerate big dreams. (Learn more about membership here.)

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