Many meaningful seasons of growth can be traced back to a single decision: the moment a leader chose to invest, even when the outcome was not guaranteed. Not every investment pays off in the same way, but the ones that do can change what comes after.
We asked business founders and leaders, all of them members of the Dreamers & Doers community, to reflect on the investment that helped lead to a major growth unlock. From the specific areas they chose to prioritize to the tangible shifts that followed, their answers offer a behind-the-scenes look at what it can take to scale.
For founders building toward their next milestone, their stories offer a reminder to think carefully about where, and how, they invest in themselves and their businesses.
Investing in People
Perhaps the most traditional, and enduring, way to invest in a business is by investing in its people. Even innovative leaders often come back to this fundamental strategy, allocating capital toward executive hires, fractional expertise, and strategic team additions that can position the business for its next stage of growth.
Just three months into starting her boutique executive search and career development platform Ask a Chief of Staff, Clara Ma took this leap and hired an executive assistant.
“It felt early for our size, but I was getting buried in scheduling and admin, the exact work pulling me away from actually building,” the CEO says.
Bringing on an executive assistant despite her misgivings about timing proved to be an effective strategy. Within six months, Ma was able to launch Ask a Chief of Staff’s community product line, which is central to the business today. Finding the right person to take on the tasks distracting her from that strategic planning made it possible.
Other founders have seen benefits from investing in professionals with more specific expertise. Natalie De Vincenzi, the founder and CEO of You Are Enough Co., calls hiring marketing and advertising support “the smartest move” she made. The investment helped grow the reach and community for De Vincenzi’s mental health apparel brand, ultimately supporting increased sales.
For Kimberly Tara, a tax accountant was the right investment. While the founder and CEO of The Tara CPA Firm thought she would be a solopreneur forever, she is glad she made the leap of faith with this hire, after weighing the numbers.
“This freed up my time to work on operations, marketing, growing the firm and the bigger picture,” Tara says.
Bringing this expert into the fold helped improve revenue and made Tara a believer in the power of a team. Less than three years after making that first hire, her business now has a team of six. Each operator serves an important function that strengthens the mission and helps the founder stay in her zone of genius.
Investing in Marketing and Customer Insight
While bringing marketing experts onto the team is one way to deepen a leader’s understanding of customers and performance, it is not the only route to more informed decision-making. Many founders find that strategic investments in research, data, and customer insights can unlock clarity that is just as valuable.
GreenPortfolio CEO Bonnie Gurry invested in customer research that revealed important truths about her target audience of affluent professionals. Armed with the knowledge that these prospective clients were not skeptical of sustainable investing and simply did not have time to figure it out for themselves, her team changed its approach.
“We stopped giving people more information and built a streamlined advisor-matching service that does the heavy lifting for them,” Gurry says, adding that the shift is what took her business to the next level.
In her role as Chief Swag Officer of Go to Market, Amanda Hofman has prioritized developing a deeper understanding of the business her company already has. Investing time in reviewing and analyzing her sales conversations has supported meaningful returns.
“I review my sales calls using AI to identify patterns, blind spots and opportunities I would have missed on my own,” Hofman says. “Getting that level of feedback several times a week has made me a stronger salesperson, increased my confidence and helped us grow much faster than if I were relying on instinct alone.”
Investing in Systems and Infrastructure
When identifying opportunities for growth within her web design agency Beautifuli Digital, Liane Agbi knew that a streamlined system was the wisest strategy. The founder invested in reorganizing her project management systems, client onboarding workflows, and design delivery infrastructure, moving from scattered spreadsheets and email chains to integrated, automated systems that allowed her team to scale without sacrificing quality.
“It was the unlock that transformed Beautifuli Digital from a solo operation into a scalable business because it freed me from being the bottleneck and allowed my team to operate autonomously and efficiently,” Agbi says.
After making this sizable investment, her team was able to take on up to four times as many projects without adding proportional headcount. Revenue increased, employees were happier, and Agbi no longer felt like everyone was waiting on her to make decisions and move.
“Investing in systems wasn’t just about growth metrics,” she says. “It was about creating space for the creative work that matters. When your back-end operations are solid, your team can focus on what they do best.”
Investing in Community and Network
For founders and solopreneurs, creating the conditions for success is often just as important as executing the work itself. Because entrepreneurship can be an isolating journey, many intentionally invest in communities and professional networks that provide support, perspective, accountability, and opportunity. It is an expense they say has become one of the valuable investments they have made in their businesses and themselves.
“Joining paid communities was the investment that quietly changed everything,” says Nicole Leon, founder of L. Leon Virtual Assistance. “Proximity to the right people, honest conversations, referrals that came from actually showing up and being known- that’s what helped us recover a major budget cut from a client in under a month.”
Leon notes that a founder’s return on investment into community is rarely linear or immediate. She encourages her fellow leaders to look at it as an ongoing growth strategy focused on proximity and relationship-building.
Tavlin Consulting CEO Allison McMillan reflects a similar experience.
“My biggest unlock was being intentional about community, choosing a small number of networks to invest in deeply rather than spreading myself across every room I could get into,” she says. “The ones I committed to don’t just offer one thing; they cheerlead me, send business my way and give me the advice and mentorship I’d never get on my own. Showing up consistently for those is what turned a network from a contact list into actual momentum.”
Intentional communities can offer support and connection, but some founders seek them out for something more specific.
For Colleen Krieger, open and honest conversations about money, often a complicated topic, were a big draw for this sort of networking.
“Money is a taboo subject for women, especially women coming from corporate backgrounds,” says the founder and fractional CMO of Superbloom Strategies. “We’re taught that it’s impolite to ask questions about finances or share with others. That mindset is holding us back. The best investment I made was in building community and spending time with my network early on to get comfortable asking the uncomfortable questions about money. It helped me understand market rates and my own value, so I had the data I needed to price and negotiate contracts with confidence.”
Investing in Personal Capacity
Today’s founders and leaders also recognize that some smart business investments happen outside the business itself. They have expanded the meaning of “spend money to make money,” directing resources toward the parts of their lives that help them think more clearly, lead more effectively, and show up at their best.
When Samantha Musser saw an Instagram ad for a women’s retreat on Nantucket, it did not take long for her to decide to make the five-figure investment that would allow her to participate. The program gave Musser the chance to work with a nervous system coach who facilitated what she describes as a game-changing identity shift for the owner of Twofold Financial.
“I stopped thinking of myself as too introverted and quiet to deserve a seat in rooms with women running businesses so wildly different from my own,” she says. “That shift is what allowed me to delegate, work on the business instead of in it, stay calm through a two-month client drought and build the kind of relationships that turn into referrals.”
Other types of coaching and professional development have proven similarly meaningful for founders in other spaces, like Sydney de Arenas, who had spent more than a decade building multiple companies. Even with that experience, de Arenas benefited from hiring a coach who had been exactly where she was.
“It showed me that my businesses could only grow as far as I was willing to grow,” says the founder of The Hive. “That investment changed how I lead, how I make decisions and how courageously I show up, helping me become the woman and leader I always knew I was meant to be.”
Beth McNamee is so passionate about professional development that she includes it as a core line item in the annual business plan for her consulting business. Most recently, she made five trips from Los Angeles to Amsterdam to secure a certification in Systemic Intelligence and Organization Constellations. The resulting skillset and community, she says, has helped her move closer to where she hoped to be.
Before building a company dedicated to placing house managers, Kelly Hubbell experienced firsthand the payoff that came with investing in this sort of personal support. She needed it to unlock her personal capacity by getting more help in her daily life, and in securing it, became her own first customer for Sage Haus. Today, her team serves thousands of families seeking similar support.
For Relatable Nonprofit founder Catalina Parker, investment in capacity means everything from therapy and retreats to health support and daily wellness practices.
“They helped me notice the patterns and limiting beliefs that were affecting how I made decisions, showed up in relationships, and ran the business,” Parker says of these investments. “The more I invest in myself, the better the business does, because I’m leading from a much healthier, clearer place.”
Every founder’s growth unlock looked different, but the underlying principle was consistent: meaningful growth often required intentional investment before the payoff was guaranteed. Whether that meant hiring the right person, strengthening systems, joining the right community, or investing in their own capacity to lead, these founders chose to bet on the future version of their businesses.
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.)
