This episode is a bit different from our usual format. Instead of hosting a guest, I'm taking the hot seat to address the questions that have been hitting my DMs.

We'll be exploring a range of topics that are crucial for founders and entrepreneurs in 2024. From the strategic advantages of outsourcing to the challenges of managing remote teams across different cultures, we'll delve into the nitty-gritty of building and scaling a business. We'll also touch on some of the personal challenges that come with being a founder, including managing mental health and finding support networks.

Whether you're a seasoned entrepreneur looking to optimize your operations or a first-time founder navigating the complexities of starting a business, this Q&A session will give you some practical insights and actionable advice.

So grab an empanada (or your comfort food of choice), and let's dive into these questions that are shaping the future of entrepreneurship and global business.

For those that prefer listening to reading, be sure to catch the full episode here:

Why did you start a podcast where you eat empanadas with founders?

About a month and a half ago, I brought my Philippines leadership team at NeoWork to Colombia for our team retreat. One of my fondest memories is all of us coming together over empanadas. Despite being on opposite sides of the world, both countries share colonial Spanish ties, resulting in surprisingly similar culinary traditions.

If you go to a restaurant in either country, you'll hear familiar words like tenedor (fork), vasada (glass), and mesa (table). Empanadas are super popular in both places, making them the perfect accompaniment to our conversations. I found it fitting to dive deeper into uncomfortable topics with some of my founder friends over this shared comfort food. It's a unique way to bridge cultures and create a relaxed atmosphere for discussing the challenges and triumphs of entrepreneurship.

Why should I outsource instead of hiring a recent college grad?

I've been through the wringer with this one. When I was at Bird, we initially hired a lot of recent college grads for support roles. The challenge we found went beyond just cost considerations. Within the first three to six months, many of these recent grads and interns were eager to move into different departments, like marketing or launching new cities with Bird. Meanwhile, we still needed to fulfill the core functions of answering support tickets.

The strength of outsourcing, particularly to countries like the Philippines, is that a support role is seen as a career instead of just a job. The pay is very competitive, often comparable to what university professors make in the Philippines. These professionals can support their whole families and find fulfillment in advancing their careers within customer support, eventually becoming supervisors or working on quality assurance.

I found the level of effort and dedication to the role to be significantly higher compared to US-based recent graduates. Plus, there's a maturity factor to consider. Recent college grads, typically under 25, are still developing professionally. I've seen issues with typos, lack of punctuality, and sometimes unprofessional decision-making that can negatively impact brand representation.

When you're building a business, especially in the early stages, you need a team that represents the elite level of your brand. Outsourcing to experienced professionals who see support as a viable long-term career can provide that level of dedication and professionalism.

I've had a bad experience in the past with outsourcing to the Philippines where they just ghosted after a few days. How do I address that or stop it from happening in the future?

I actually started NeoWork to address this exact pain point. I used to be in the client's shoes and saw a really high turnover rate with these outsource teams. To answer your question, it really comes down to onboarding and training.

There's not a lack of talent overseas, but there is often an inequality in how these professionals are trained, onboarded, and managed as employees. I've seen some pretty shocking practices, like BPOs not even providing toilet paper to their employees out of fear it would be stolen.

When I started NeoWork, my number one priority was to approach employee benefits and recognition the way top US startups do. We focus on setting very clear expectations during training and onboarding about exactly what the role will entail. We invest heavily in our team members' professional development and skills training, making them feel like they're earning beyond just their salary with this role.

By addressing these factors and treating our team members as valuable long-term assets, we've been able to significantly reduce turnover and create a more stable, reliable outsourcing experience for our clients.

How did you handle the typhoon in July in the Philippines?

That was a challenging situation. The Philippines is part of the Pacific Ring of Fire, which means it's prone to natural disasters like typhoons, earthquakes, and volcanic eruptions. This geographical reality necessitates robust business continuity planning when working in the region.

To give you an idea of how unpredictable it can be, back in 2020, right before the pandemic, I flew out of Manila just two hours before the Taal volcano erupted. It's that kind of unpredictability that we've had to factor into our operations.

At NeoWork, we've been very intentional about setting up our teams in pods. They work remotely, but within close geographical proximity in areas like Metro Manila, Naga, and Cebu. This setup allows us to have backup plans in place for when natural disasters strike.

When the recent typhoon hit last month, our business continuity plan kicked in. After the immediate danger had passed, but while there were still power outages and internet issues, our team members were able to go to one of our backup sites. These sites are equipped with Starlink internet and generators, allowing us to continue operations for our clients even in challenging conditions.

But it's not just about maintaining business operations. We also make sure to take care of our teammates' immediate needs, providing food, transportation, and any necessary medical assistance. It's about balancing business continuity with genuine care for our team members' well-being.

Joshua, how do you work through depression as a founder?

This is a deeply personal question, and I appreciate the opportunity to address it. I spent about a year and a half of my life in bed during my early 20s in college, grappling with depression. It wasn't a lack of happiness per se, but more a feeling of being a zombie.

Through this experience, I learned a lot about listening to my body and prioritizing self-care. Honestly, I've found exercise to be the best antidepressant on the market. It's a non-negotiable part of my schedule - a blocked-out part of the calendar that can never be moved.

I also pay close attention to my diet and how different foods affect my mood and energy levels. Learning to recognize the early signs of burnout and paying attention to that internal chatter in your mind is crucial. Don't lock these feelings away - address them head-on.

I've found it helpful to view my depression as a part of me that's trying to communicate something important. Is it telling me to slow down? To be more mindful about my health and sleep? If so, depression might actually be trying to help me.

I often think about the movie "Inside Out" and the idea of having different emotional parts within us. Instead of trying to block away the uncomfortable parts, I try to embrace them and understand what they're telling me. Remember, being a founder is challenging, and it's okay to struggle sometimes. The key is to develop healthy coping mechanisms and to seek help when you need it.

I'm starting my first company - what's your biggest piece of advice?

My biggest piece of advice is to find your circle of peers. Being a founder can be an incredibly lonely role. There are going to be a lot of day-to-day challenges that come up that you can't really share with friends and family without them fully understanding what you're going through.

Finding a peer group of like-minded founders can be invaluable. I recommend programs like YCombinator, OnDeck, or other founder communities. These networks allow you to learn from the expensive mistakes others have made and provide a safe space to confide in others about the day-to-day challenges of being a CEO.

Having this support system has been crucial for me in making it through the marathon of entrepreneurship. It's not just about sharing struggles - it's also about celebrating wins, bouncing ideas off each other, and sometimes just having people who truly understand the unique pressures of founding a company.

Why do you outsource talent from Colombia?

While the amazing empanadas are certainly a perk, there are several strategic reasons why we source talent from Colombia, particularly from Medellín.

Medellín has emerged as one of the major tech hubs in South America. In fact, there's currently a friendly rivalry between Medellín and Santiago, Chile, over which city will become the "Silicon Valley of South America". This means there's an incredible pool of tech talent in the region.

But it's not just about tech roles. For Spanish-language support roles, Colombia offers a unique advantage. The Medellín accent, known as "paisa", is universally regarded across Latin America as very appealing and easy to understand. Many voice actors are based in this region because the accent is neutral and easily understood across all of Latin America and by Spanish speakers in the U.S. market.

This linguistic advantage, combined with the growing tech ecosystem and the cultural affinity I've developed for the country, makes Colombia an excellent source of talent for our operations.

How does the management structure work with outsourcing? Are they an extension of my internal team or managed through NeoWork? Any advice for success?

This is a crucial question, and I'm glad you asked it. I've seen many companies, especially larger enterprises, make a huge mistake by treating their outsourced teams as completely separate entities. They often hand off responsibilities like customer support with a "figure it out for us" attitude. This approach is a recipe for disaster.

For outsourcing to be successful, it's essential to integrate your outsourced team with your internal team. Ensure your outsourced team aligns with your brand voice. They should understand and embody your company culture and values. Especially for startups that experience rapid operational changes, it's crucial to keep your outsourced team in the loop. Include them in your Slack workspace or whatever communication tools you use internally. More than anything, your outsourced team should feel a sense of ownership. They should feel like genuine members of your internal team.

Invite them to be part of your Slack community, weekly huddles, or whatever team-building activities you do with your internal team. The best way to approach outsourcing is to welcome your outsourced team fully and make them feel no different from your U.S.-based employees. Remember, these team members, although geographically distant, are an extension of your company. The more integrated and valued they feel, the better results you'll see in terms of productivity, loyalty, and quality of work.

Wrapping Up

I want to thank you all again for your support over the first month of Founders & Empanadas. I'm excited about the future of this series and can't wait to bring you more insights and conversations. If you ever need help or have more questions, please don't hesitate to reach out to me on LinkedIn or directly through NeoWork.com. Talk to you soon!