You might start your career with one plan, only to have it completely change course. That’s what happened to Rob Hoffman. He set out to be a writer, chasing journalism dreams, but ended up in sales at a struggling startup. Instead of letting that derail him, Rob leaned in, and in his first year, he closed half a million dollars in deals. The next year, he doubled it.
That success became the base for building Contact Studios, where Rob now leads as CEO. He combines his deep content knowledge with sharp sales skills to help marketers scale their content output without hiring more people.
On the Founders and Empanadas podcast, Rob shared what founder-led sales really feels like, the pressure, the doubts, and the wins. He talked about why authenticity matters when closing deals and how using a mix of skills can change the game.
If you’re running a startup and trying to grow without burning out, Rob’s experience with building a sales team and stepping back from being the only closer offers lessons you can use right now.
Key Takeaways
- Authenticity Beats Perfection: Rob's success came from being genuine rather than following rigid sales scripts. His Superman poster backdrop and creative showmanship proved more effective than polished presentations.
- Question-Based Selling Reduces Pressure: The best salespeople ask questions rather than pitch constantly. This approach makes prospects feel heard while taking pressure off the salesperson to have all the answers.
- Leverage Your Unique Background: Rob's writing skills gave him research abilities and storytelling techniques that differentiated his sales approach. Every background offers transferable skills for business success.
- Document Everything for Scaling: Transitioning from founder-led sales requires systematic documentation through tools like Loom videos, allowing new team members to pattern-match your approach at 90% effectiveness.
- Mental Health Drives Performance: Managing the emotional toll of sales through dedicated personal time isn't just self-care—it's essential for maintaining the energy and positivity that prospects respond to.
The Unconventional Path from Favela to Fortune
Rob's story begins with a dramatic career pivot. After getting fired from a Toronto startup along with 39 other employees, he saw an opportunity rather than a setback. "I was miserable in Toronto," Rob shared on the podcast. "Getting fired meant I could finally move back to Medellín, which was all I really wanted in life."
With just $10,000 in savings, Rob moved to one of Medellín's less economically developed neighborhoods, a place so rough that taxi drivers would ask "Are you sure?" when he gave them his address. He was paying just $70 a month for rent in what he describes as "a bit of a favela."
When the same startup that had fired him reached out nine months later, Rob jumped at the chance to rejoin, but this time as an entrepreneur, not just a writer. "I didn't see myself as a writer anymore. I saw myself as an entrepreneur," he explained to podcast host Joshua Eidelman.
The transformation was immediate and dramatic. On his first day in sales, Rob closed a $133,000 deal. His secret weapon? A Superman poster strategically placed behind his desk to hide the unfinished concrete walls of his modest apartment. "I'd take this stupid Superman poster and put it behind me, and that was like my good luck charm for closing deals," he recalled with a laugh.
That year, Rob closed half a million dollars in deals. The following year, he doubled it, hitting a million. But for him, success wasn’t only about the numbers. It was about proving that being authentic and confident can break through any barrier, even when you’re starting in a place most would see as a disadvantage.
Managing the Emotional Toll of Founder-Led Sales
Founder-led sales can be brutal, and Rob doesn’t shy away from that reality.
In his chat with Joshua Eidelman on Founders and Empanadas, he opened up about how emotionally taxing sales can be when you’re also juggling all the other roles of a founder.
“Sales is so emotionally toxic. It’s such an emotional labor... What I find is really helpful, especially because sales is such a social thing, you really have to be turned on, put your best foot forward... so I think just creating space where you can kind of have time to yourself.”
Rob’s way of protecting his mental health is simple but effective: set aside personal time that’s off-limits for work. “For me, I love just going to the park and carving out like an hour of my day that’s non-negotiable where I’m going to just sit, maybe watch the sunset, read a book, and just have me time.”
One of the biggest challenges in sales is facing rejection. But Rob encourages you to change your perspective. “The hardest part about sales is just dealing with a ton of nos,” he said. “If you just say, ‘I’m going to put this mental armor on and be okay with having many people say no to me,’ then you can build a great business.”
The Art of Question-Based Selling
One of the most valuable strategies Rob shared on the podcast was his approach to sales calls, which he describes as question-based selling:
"The best salespeople ask a lot of questions. So create a document where you have a little bit of a script for the opening that you're gonna give... After that, it's just a lot of asking questions. And that takes the pressure massively off of you because your job is pretty simple. You're just kind of sitting there. You're like a doctor diagnosing a patient by asking questions."
This approach serves multiple purposes. It takes pressure off the salesperson, allows for better discovery of client needs, and creates a more consultative rather than pushy dynamic. Rob emphasized that the goal is to talk as little as possible while learning as much as possible about the prospect's business and challenges.
The Power of Authenticity and Showmanship
Throughout his interview with Joshua Eidelman, Rob consistently emphasized the importance of authenticity combined with strategic showmanship. His philosophy challenges conventional sales wisdom that focuses on rigid scripts and manipulation tactics.
"People just want to work with people who they trust and who they like," Rob explained. "95% of it is just empathizing and being a genuine, kind of trustworthy person."
For Rob, sales isn’t about faking it. It’s about building real trust through empathy and honesty. But he also knows that being genuine alone isn’t always enough to stand out in a crowded market. That’s where his creative showmanship comes in.
When pitching Dribbble, a company with a basketball logo, Rob actually spun a basketball on the call. For a prospect with a green mustache logo, he crafted a green cardboard mustache on a stick and wore it during the presentation.
“It just shows that we’re willing to go the extra mile,” he said. “We put a little bit of showmanship in there. Now they remember us out of the other five agencies that they’ve talked to.”
This combination of authenticity and memorable moments helps Rob connect deeply with prospects while leaving a lasting impression. It’s not just about being liked—it’s about being remembered and trusted, which is what really closes deals.
Leveraging Writing Skills in Sales Success
Rob's background as a writer proved more valuable than he initially realized. During his Founders and Empanadas interview, he highlighted how writing skills translate directly to sales success:
"Being a writer is actually super advantageous in business and in sales for many reasons, but one area in particular is knowing how to do proper research."
His journalistic training taught him to approach each sales call like an investigative story. "Ideally what you want to do is put your investigative journalistic hat on before a sales call and try to figure out, what's the story behind this company?"
This research-first approach allows Rob to:
- Understand the prospect's background and interests
- Identify conversation starters beyond business
- Demonstrate genuine interest rather than treating prospects as numbers
- Uncover the company's trajectory and challenges
Building and Recruiting a Global Team
Rob’s experience building Contact Studios’ team, including operations in Colombia, offered important lessons about recruitment, especially for founders handling sales themselves.
His philosophy on hiring reflects the same authenticity he values in sales.
“Most people just want to work for somebody who they see as legitimate and trustworthy and inspiring,” Rob shared. “And it doesn’t need to be that your company is going to change the world. It just might be, ‘Hey, we’re building something pretty interesting, pretty cool.’”
For Rob, successful team building comes down to:
- Genuine enthusiasm and energy that’s contagious
- Clear progress toward real, defined goals
- Honest communication about the challenges and the journey ahead
- Creating an environment where people can see and feel growth happening
This approach helps attract individuals who share the company's mission and aspire to grow alongside it, rather than those seeking only lofty promises.
Transitioning Out of Founder-Led Sales
As Contact Studios has grown, Rob has had to confront every founder's eventual challenge: transitioning away from being the primary salesperson. His solution, shared during the podcast, is elegantly simple yet highly effective.
"To transition yourself out of your role, really what you want to do is just document everything that you do. And the best way of doing that is through Loom videos," Rob explained to Joshua Eidelman.
His approach removes the pressure of creating perfect training materials. Instead of narrated, polished presentations, Rob records himself naturally going through his daily sales activities, preparing for calls, conducting research, handling objections.
"People are really good at pattern matching," he noted. "So if I just film a video of myself—it's just like a 20-minute, no narration video of me preparing for a sales call—I can then take and hand it over to a salesperson who I'm going to be hiring."
Contact Studios has built a comprehensive repository of these Loom videos covering everything from lead qualification to the differences between discovery and proposal calls. This approach enables new team members to adopt Rob's methodology with 90% effectiveness, eliminating the need for his direct involvement in every interaction.
Content as a Sales Multiplier
Rob’s unique blend of content expertise and sales skills gives Contact Studios a real edge. In his interview on Founders and Empanadas, he explained how content serves as both a lead generation tool and a trust-building mechanism.
"Content is kind of everything these days, mainly because people want to see that you are active on social platforms like LinkedIn before they buy from you. Buyers are more sophisticated than they've ever been."
His content strategy serves multiple purposes:
- Warming up leads before sales conversations
- Demonstrating expertise and thought leadership
- Building familiarity so prospects feel they already know him
- Creating trust through consistent value delivery
The synergy between content and sales creates a powerful flywheel effect. Rob's sales conversations often inform content ideas, while his content creates qualified inbound leads who are already familiar with his expertise.
Lessons for Growing Companies
Rob Hoffman's journey from writer to million-dollar closer offers several additional insights for founders navigating sales challenges:
- Embrace Your Background: Rather than seeing his writing background as irrelevant to sales, Rob leveraged research skills, storytelling ability, and content creation expertise to differentiate his approach.
- Authenticity Over Tactics: While sales techniques have their place, Rob's success stems from genuine enthusiasm, thorough preparation, and creative showmanship that feels natural rather than manipulative.
- Question-Based Discovery: The most effective sales approach focuses on understanding prospect needs through strategic questioning rather than delivering perfect pitches.
- Content Amplifies Sales: In today's marketplace, content creation and sales success are interconnected. Prospects research thoroughly before buying, making thought leadership content essential for trust-building.
Building the Future of Content Production
Today, Contact Studios helps marketers scale their content production efficiently, allowing companies to increase output without proportionally increasing headcount. Rob's journey from that Superman poster in a Medellín favela to leading a successful content agency demonstrates how unconventional paths can lead to extraordinary outcomes.
What does this mean for you? First, don’t see failure as the end of the road. For Rob, losing a job was actually the start of a new opportunity. Failure can be part of the path to success if you learn from it.
Second, being authentic matters. Rob’s genuine approach, combined with strategic thinking, helped him turn what seemed like disadvantages into strengths.
If you’re facing challenges growing your business or team, Rob’s journey shows that staying true to yourself and thinking creatively about growth can lead to unexpected and impressive results.
This article is based on Rob Hoffman's appearance on the Founders and Empanadas podcast, hosted by Joshua Eidelman, founder of NeoWork. In this engaging conversation, Rob shared valuable insights on entrepreneurship, sales strategies, team building, and scaling content operations. The full episode explores even more of Rob's journey and business wisdom.
