Ted Guggenheim once took more than a dozen cowbells into a recording studio. The assignment was to find the right ring for an iPhone app aimed at spectators of the 2010 Winter Olympics. A phone would impersonate a bell. Before it could do that convincingly, somebody had to listen to the real ones. Guggenheim, a music industry veteran who had worked with Sting and managed The Samples, was well placed to conduct this slightly peculiar audition.
The result, Cowbell2010, cost 99 cents. Fans could dress their virtual bell in a national flag and make themselves heard without clapping through mittens. Rage Digital, the three-person Boulder company behind it, also supplied schedules, medal counts and a feed from more than 150 Olympians. It was a small product with an unusually attentive ear. The joke was in the premise; the work was in getting the sound right.
Guggenheim would later become known for a quieter signal: the text-message reply. As co-founder and CEO of TextUs, he helped turn a familiar phone habit into software for businesses. His working life has since included another recruiting technology company and, with his wife Trish, an indoor pickleball club. The job titles change considerably. The audience keeps its vote.
An audience before an inbox
Guggenheim graduated from the University of Colorado Boulder with a business degree in 1986. Music became part of his professional life before software did. Years later, when he talked about entrepreneurship, the comparison he reached for was managing a band: keeping the enterprise alive long enough for something to connect. The album and the product arrive in different packages. Both require an audience willing to give them a chance.
That comparison gives his career a more useful shape than a list of industries. A band manager has to attend to the people making the work and the people receiving it. A software founder inherits a similar double obligation. A product may please its creators while leaving its intended customers indifferent. Getting those two groups into agreement is a substantial part of the job.
There is also something reassuringly concrete about the cowbell episode. Even a novelty app had a detail worth fussing over. Guggenheim had changed businesses without entirely leaving the sound studio behind. A new medium had given an old skill another assignment.
The phone already knew how
By 2013, Guggenheim and his Rage Digital colleagues Andrew Kimmell and Mike Hickman were pursuing business texting. The app market had grown crowded. Texting offered an established behavior without the preliminary chore of persuading each customer to discover and download another app. “Everybody text-messages,” Guggenheim said. His argument began with what people already did.
Early TextUs.Biz products show how broadly the team explored that idea. One enabled text messaging on ordinary ten-digit business landlines. Another, iPad Receptionist, grew from a request by the venture capital firm Foundry Group: visitors could announce themselves on a tablet and notify the person they had come to see. A restaurant waitlist product was also in development. A vacant front desk and a waiting diner both suggested uses for a short message.
The early picture is less tidy than the later company description. Several practical experiments sat under one proposition: a business could use the phone more conveniently. “Phones bottleneck, but not texts,” Guggenheim said. The attraction was the reduced effort required to get a conversation started.
- MusicManage the performers
- Mobile appsMake the phone useful
- Business messagingHelp the reply arrive
- Indoor courtsBring people together
A salesperson changed the conversation
TextUs initially expected small businesses to provide its market. In 2015, the company hired its first full-time salesperson, Erich Hugunin. He knew staffing and recruiting and recognized an application there. Recruiters were already using their personal phones to contact candidates. The behavior existed; the business infrastructure around it was the opportunity.
For Guggenheim, the discovery narrowed the problem. Someone at work or moving between commitments could answer a brief message more readily than take a call. A recruiter often needed an indication of interest or availability before proceeding. Even a refusal was useful, because it allowed the conversation to move on. Speed mattered in a market where another agency could reach the same candidate.
The revealing part of this episode is the colleague’s contribution. The company found direction through someone who understood a particular customer. A founder’s original plan had room to accommodate another person’s experience. Plenty of business plans become more persuasive after that happens, although the revised version rarely gives the first draft much credit.
The reply had to fit the working day
A useful channel still had to belong inside a recruiter’s workflow. In September 2016, TextUs announced that its hundredth staffing firm had selected the service. That milestone counted organizations, rather than treating every message sent as evidence of a relationship. The product was finding buyers in a defined industry.
Integrations made the practical case clearer. In October 2018, TextUs added Greenhouse, allowing users to send and receive personalized messages from their applicant tracking system and record those contacts in candidate profiles. A text sent from a private phone may produce an answer. A text connected to a candidate record can become part of the shared work.
In May 2019, Guggenheim advocated a “Text Us” call to action that would let people begin a conversation from a website, email or elsewhere online. The front door deserved attention too. A business could spend considerable effort persuading somebody to visit, then make the final step feel like paperwork. The proposed link shortened the distance between interest and a person who could respond.
Growth, with a date attached
In August 2018, TextUs debuted at number 573 on the Inc. 5000. The company reported 886 percent growth from 2015 through 2017 and annual revenue above $2.4 million. Those figures mark a particular stretch of Guggenheim’s leadership. They give the recruiting turn a measurable consequence without requiring his entire biography to become a scoreboard.
By February 2020, TextUs reported serving more than 75,000 professionals. An initial Series B close, combining new equity and an expanded debt facility, provided $5 million of additional capital. The company planned to invest in products, its team and its staffing business. Its TextUs Next platform brought voice and messaging into a dashboard connected to customer or applicant records.
Guggenheim’s earlier leadership advice placed limits on what money and features could accomplish. He urged future CEOs to understand the customer’s problem and accept responsibility when things went wrong. A funding announcement can buy time and resources. It leaves the daily obligation to make something people will use quite intact.
The band gets back together
Staffing Engine’s public launch in 2021 brought Guggenheim back together with former TextUs collaborators, including Kimmell and Hickman, alongside co-founder Jay Cutler. The new venture applied conversational AI to staffing. Website chat, messaging and handoffs to recruiters could sit within tools teams already used. The company’s promise again concerned the awkward pause between somebody showing interest and somebody responding.
Matt Dichter, who joined to lead sales after eight and a half years at Bullhorn, supplied a telling detail. Guggenheim had tried to recruit him to TextUs for years. The timing had never aligned. Staffing Engine finally gave him an opportunity to join early, with a team he knew and a problem he wanted to tackle. A business relationship had survived the unanswered recruiting pitch.
The technology had changed from the TextUs days. The concern about adoption remained recognizable. Connecting a new conversation to familiar collaboration tools gave the recruiter less to rearrange. For the customer, convenience is part of the purchase. For the employee asked to use the product, it can determine whether the purchase ever becomes a habit.
“Speed of communication is critical to a staffing agency’s success.”Ted Guggenheim, 2017
Seven courts, and a different kind of return
By December 2025, Ted and Trish were preparing an indoor pickleball facility in Goleta’s Fairview Shopping Center. A former Bed Bath & Beyond store would house seven courts. Their venture initially operated under The Picklr franchise. The planned setting included a community lounge and equipment for practice. Here the invitation would lead through an actual door.
In September 2026, the couple announced a break from the franchise and a new name, The Grove Pickleball, recalling the lemon grove that once occupied the property. They proposed lower prices and a player pass system that would welcome occasional customers alongside regulars. Guggenheim said the franchise model had proved a poor fit for the local community. The decision made the business more directly theirs to shape.
The couple’s local venture brings a familiar business question unusually close: who is the offer for, and what will persuade that person to come back? Seven courts make the answer visible. There are spaces to fill, preferences to hear and people with other ways to spend an evening. A software dashboard can represent a customer. A court lets the customer arrive.
Guggenheim’s career has moved through music, apps and messages to a place where the audience carries a paddle. The cowbell recording session remains a pleasing opening detail, because it shows someone attending to a small experience before asking people to buy it. The latest business asks for another kind of response. This time, people can give it by turning up to play.