Paige McPheely’s move into software began with a service business that could not meet demand quickly enough. At 33Vincent, the remote executive assistant company she cofounded, prospective customers sometimes faced an eight-week wait. The business needed more people prepared to do the work.
In this Founder Factor conversation, McPheely explains how that constraint led to Base, why the two businesses eventually came together, and how she learned to lead a venture-backed company. Her account keeps the human side visible: assistants learning their work, employees experiencing uncertainty, and a founder deciding what she can responsibly promise.
What you'll learn.
- Base grew from observing the training and workflow challenges of a remote assistant service.
- Repeated investor conversations helped McPheely learn fundraising, while introductions and experienced support opened doors.
- A written guide to working with her made leadership expectations more explicit.
- Cash planning, hiring discipline, and respect for employees remained necessary alongside growth ambitions.
An eight-week wait exposed the service’s constraint.
McPheely and a friend had started 33Vincent as a remote executive assistant staffing company. Over time, finding enough prepared assistants became difficult. Customers often arrived when they already urgently needed help, so asking them to wait two months meant losing business.
The team also saw new assistants struggle with disconnected processes and the amount they needed to learn. Across many client relationships, they could observe how experienced assistants worked, but individuals were still repeatedly figuring things out for themselves.
That combination prompted a software question: could useful working methods become easier to follow through a product? McPheely describes the idea developing gradually from frustration and need, with the long waitlist making the cost of inaction particularly clear.
The product was designed as the assistant’s workspace.
McPheely describes Base’s software as a private space for assistants. At the time of the interview, the executives they supported did not have direct access. Assistants could choose which outputs to share with them.
This product boundary reflected who needed help doing the work. The aim was to make good practices easier to use within the software. McPheely also explains that the staffing business worked with contractors, which affected how it could direct their activities. That is her account of the operating constraint that informed the product, rather than a general statement of employment rules.
Base was also developing training and community offerings. After bringing 33Vincent under its umbrella, the combined business offered routes to part-time assistant support and custom full-time searches, with placed assistants using the software. Marketplace and further training ideas are described as directions the business was pursuing, not finished features in every case.
Fundraising became a skill learned through practice.
McPheely had not previously raised venture capital, hired software engineers, or worked closely with software development. She credits High Alpha, the Indianapolis startup studio that invested in Base, with resources and peers who helped her understand those unfamiliar parts of the job.
Reaching that support took time. Existing 33Vincent clients made introductions after hearing what she wanted to build. Those connections eventually led to High Alpha through a process she describes as involving many steps over many months.
She also recalls unsuccessful investor conversations before she understood what the audience expected. Her advice is to practice with investors who are not at the top of a founder’s preferred list. Repetition exposes difficult questions and gives the founder a chance to improve the explanation before the most important meetings.
A written guide made her leadership easier to understand.
McPheely discusses learning to stay authentic in venture-backed technology, where she often found herself among people whose ways of talking about work differed from hers. She wanted to become an effective leader without hiding the rest of her life.
One practical step was writing a user manual for herself. The document describes how she works well with people, what frustrates her, and what happens when she is struggling. Leaders joining the company receive it as a starting point for discussion.
The exercise made her examine her own habits and gave colleagues permission to discuss them. That matters particularly in a remote company, where important expectations can remain unspoken. Instead of asking teammates to infer her preferences from occasional interactions, she tried to put enough information in front of them to have a direct conversation.
Three responsibilities helped her decide where to spend time.
McPheely organizes her role around representing Base publicly, setting the company’s direction, and ensuring the team has the resources to do its work. Those resources include capital, a workable budget, and capable people.
The acquisition brought her former 33Vincent cofounder into the combined company as president. Having another leader at the helm created support, but it also required attention to how the organization would work after combining two teams.
These responsibilities helped McPheely redefine a successful day. She describes herself as someone who likes completing tasks, while leadership increasingly involves work that takes months or never reaches a simple finishing point. A request outside her main responsibilities became a reason to consider delegation or hiring, rather than automatically adding another task to her own list.
Planning for uncertainty required customer and cash awareness.
The interview takes place amid concern about a possible recession and more difficult fundraising conditions. McPheely describes reviewing customers across the software and services businesses to understand who might be vulnerable and beginning conversations with them early.
She also discusses recurring revenue, adjusted growth assumptions, and continuing to hire carefully. Those were plans and expectations at the time, rather than outcomes established by the conversation. She explicitly avoids describing the company as recession-proof.
For founders expecting to raise money, her emphasis is on showing that customers buy, remain satisfied, and continue working with the company. Later, she describes the painful consequences of mismatched hiring and fundraising timing: Base had conducted layoffs when the alternative was running out of cash. She says she would revisit some hiring decisions, particularly while establishing a new category and route to market.
Bringing software and services together solved complementary problems.
McPheely describes the merger with 33Vincent as a major celebration as well as difficult integration work. The businesses had originally been separated partly because of the investment environment she encountered. By the time they combined, she says investor attitudes toward software alongside services had changed.
The service company brought an established operation but continued facing supply and margin constraints. Base brought software, automation, and a different cost structure. Combining them meant the team could work on those connected problems together rather than recreate each other’s capabilities.
The reunion also meant working closely with her friend again. McPheely values that partnership but does not recommend starting a company with a friend indiscriminately. She says they had agreed early that their relationship mattered more than the business or money. Their experience rested on that shared priority and complementary working styles.
Respect and flexibility were part of running the company.
McPheely talks about the strain of raising three young children while running a company through the pandemic. Flexibility included reconsidering constant responsiveness and what it meant to be present at a desk. She also discusses the value she found in working with a therapist who was a professional coach.
Within the company, she wanted people to be able to acknowledge when they needed time for their mental health. Ideas about different Friday schedules were under discussion; she presents them as possibilities for healthier work, rather than settled company policy.
When asked for a non-negotiable, she chooses respectful treatment of people. Thoughtless or offensive comments still require attention even when the speaker did not intend harm. Her broader ambition is to build a successful company whose operating choices allow employees to remain healthy people.
McPheely’s story ties the product, the financing, and the workplace back to the people doing the work. A software opportunity emerged from assistants struggling with repeated tasks and customers waiting for support. Building the company then required the same kind of attention to constraints: what the team could deliver, how much cash it needed, and how its people were treated.
