#220: You Can Skip Venture Capital and Still Raise Too Much - Jerry Nettuno

Summary of #220: You Can Skip Venture Capital and Still Raise Too Much - Jerry Nettuno

by Greg Head

1h 6m•October 30, 2026
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Overview of #220: You Can Skip Venture Capital and Still Raise Too Much - Jerry Nettuno

This episode of the Practical Founders Podcast features Jerry Nettuno, founder of Schedulicity, a scheduling and payments platform built for small service businesses like salons, spas, fitness studios, and other appointment-based businesses. Jerry shares how he started the company in Bozeman, Montana, bootstrapped early, then raised roughly $28 million from angel and private investors without taking VC funding. He explains how the business grew, how COVID disrupted the model, why he ultimately sold to a private-equity-backed competitor, and what he learned about fundraising, category creation, and founder messaging.

What Schedulicity Did

Schedulicity began as a solution to a very personal problem Jerry had as a busy single father: it was hard to book simple appointments like haircuts and massages.

Core product

  • Online appointment scheduling for small businesses
  • Eventually expanded into payments
  • Built for businesses such as:
    • Hair salons
    • Barbers
    • Massage therapists
    • Fitness instructors
    • Dog groomers
    • Other local service providers

Market positioning

  • Jerry recognized early that the “competition” was often just:
    • paper calendars
    • phone calls
    • manual back-and-forth scheduling
  • The company helped normalize online booking before it was common in this segment

Growth, Traction, and Funding

Jerry describes Schedulicity as a two-sided platform with both businesses and consumers.

Key business metrics

  • Roughly 15,000–20,000 small businesses on the platform
  • About 40 million consumers used the service over time
  • Revenue at sale: around $10–20 million annually
  • Headcount before COVID: around 100 employees

Funding approach

  • Started bootstrapped
  • Began raising money as growth demands increased
  • Raised about $28 million, mostly from:
    • angel investors
    • high-net-worth individuals
    • private backers
  • No institutional VC funding
  • Jerry says capital was used mainly for:
    • hiring engineers
    • scaling support
    • accelerating marketing
    • supporting growth before revenue caught up

Why funding was useful

  • Small business software required real marketing spend to scale
  • Product development was expensive in the early SaaS era
  • More capital helped the company move faster in a very large market

Go-to-Market: How the Company Grew

Jerry emphasizes that Schedulicity grew in a market where many potential customers didn’t even realize they had a problem.

Early growth tactics

  • Early traction came from people Jerry already knew in Bozeman
  • Facebook ads were a major acquisition channel in the early years
  • The platform benefited from referrals:
    • one happy business owner would bring in multiple customers
    • customers who booked online would expect the same convenience elsewhere

Important market shift

  • The rise of booth-rental / independent stylist models in salons helped accelerate adoption
  • This meant Jerry could land individual stylists, not just salon owners, and then expand outward through their customer bases

Bozeman, Montana as a Startup Base

Jerry talks about building a software company in a place that was not known for tech at the time.

Key points

  • In the early years, Bozeman had very few software developers
  • Jerry had to recruit talent from elsewhere, including Denver
  • He says the town later changed dramatically, especially after:
    • COVID
    • the popularity of Yellowstone
    • an influx of wealthy newcomers and tech-connected residents
  • He and the host discuss how unusual it once was to build software outside major tech hubs

The COVID Shock

COVID was the biggest operational and emotional disruption in the company’s history.

What happened

  • Schedulicity’s core customers were heavily affected because they depended on in-person services
  • Appointment volume dropped almost to zero within days
  • Jerry’s daughter, who worked in a salon/spa, personally experienced the collapse in bookings
  • The company’s biggest growth period had been just before COVID, making the reversal especially painful

Jerry’s response

  • He called a leadership meeting and proposed waiving fees
  • The goal was to:
    • avoid losing customers permanently
    • support businesses that were forced to shut down
    • preserve the customer base until reopening
  • The strategy generated goodwill and publicity
  • He says it ultimately worked

Outcome

  • The team rallied
  • The company survived the crisis
  • But Jerry says the business never fully returned to its pre-COVID growth trajectory

Sale of the Company

Schedulicity was eventually sold to Vagaro, a competitor in the same space, which was backed by FTV Capital.

Transaction context

  • Jerry says the sale started as a conversation about a possible “strategic alliance”
  • That evolved into serious acquisition talks
  • The board got involved once the offer became more concrete
  • The company had also recently been through a period of major market turbulence

Why he sold

  • Post-COVID growth was weaker and less predictable
  • He worried about needing to raise another large round
  • He felt the market had changed structurally
  • The acquisition offered a reasonable exit and a softer landing for investors, employees, and the business

Deal dynamics

  • At one point, the market had supported very high revenue multiples
  • By the time of the sale, multiples had compressed significantly
  • Jerry says the deal still made sense, but the post-COVID environment changed the math

What Jerry Learned About Fundraising

One of the episode’s core themes is Jerry’s hindsight on capital.

Main takeaway

  • He says he would not raise that much money that early again
  • He believes the company could have:
    • bootstrapped longer
    • raised less
    • reduced dilution and exit pressure

Why founders often regret over-raising

  • Every round raises expectations
  • The amount needed for a satisfying exit increases as more capital is added
  • A company that might have been a good outcome at one valuation now needs a much larger sale price to satisfy everyone involved

His view on VC

  • He did not like the VC process when he tried it
  • He felt many investors were dismissive, especially because he was in Montana
  • He struggled to see the value VCs would add relative to the cost and control they would take

Advice for Founders

Jerry’s most repeated advice is very practical and message-oriented.

His top recommendations

  • Understand your market deeply
  • Be very clear about who you serve
  • Know exactly how your product helps
  • Learn to explain your company in under a minute
  • If founders cannot quickly communicate the problem and solution, they will struggle with:
    • customers
    • investors
    • partners
    • employees

Why this matters

  • In a crowded market, clarity is a competitive advantage
  • Especially for SMB products, people won’t spend long trying to figure out what you do
  • Jerry says many founders have good ideas but fail to explain them clearly enough to create momentum

What Jerry Is Doing Now

Jerry has not retired from startup life.

Current and recent ventures

  • He co-founded Pulsara, a healthcare communications platform
    • connects first responders with emergency departments
    • aims to reduce dangerous gaps in emergency communication
    • he says it is growing strongly and is now approaching $30M ARR
  • He also mentioned being involved with or considering other startup opportunities, including:
    • a live music platform called E-Resonate

Broader pattern

  • Jerry continues to work with founders and high-net-worth investors
  • He remains drawn to large markets where software can solve real operational problems

Notable Takeaways

  • Big markets can exist outside big tech hubs
  • Clear, relatable problems are easier to sell
  • Bootstrapping first can preserve flexibility
  • Raising too much capital can raise the exit bar
  • COVID exposed how fragile service-based business models can be
  • Founder storytelling and clarity are essential to growth

Bottom Line

Jerry Nettuno’s story is a classic practical-founder case: a real problem, a clear solution, scrappy early growth, non-VC fundraising, and a hard-earned lesson that more money is not always better. Schedulicity became a meaningful company by solving a simple, widespread scheduling pain point, but Jerry’s hindsight is blunt: he could have raised less, stayed leaner longer, and still built a valuable business.