Meet Roberto Penacastro Ortega from Leadsales

Q: Can you introduce yourself and your company?

A: Sure, I’m Roby Peñacastro, the CEO and co-founder of Leadsales. Our company is a conversational commerce platform aimed at helping businesses scale their sales operations. We focus on enhancing sales and improving customer response times on social media and WhatsApp. Our goal is to make communication between businesses and their customers as seamless and effective as possible, leveraging the most popular digital channels.

Q: What inspired you to start your company?

A: The concept for Leadsales emerged in late 2019 out of a necessity my brother and I faced with our own business. We needed a way to scale our operations through WhatsApp effectively. Initially, we created an internal tool to address this challenge. However, as the pandemic hit and the demand for digital communication solutions soared, we saw a significant opportunity. Our solution, which started as a simple internal tool, quickly evolved into a growing business. It resonated with many companies facing similar challenges, helping us expand rapidly.

Why Skydeck?

Q: How did Skydeck become part of your journey and what was the application process?

A: In September 2021 we had around 300 customers. My co-founder and I understood that to scale a tech startup significantly, engaging with venture capital was almost inevitable. We aimed for Silicon Valley, the heart of tech innovation, and sought out accelerators that could bridge us to that ecosystem. We applied to Berkeley Skydeck, attracted by its reputation and the potential for growth it represented. The deal on offer was $200k for 7.5% of the company, which, along with the opportunity to live and work in Berkeley, seemed like the right step for us. The application process required us to demonstrate traction and a clear plan on how we would leverage Berkeley’s network to our advantage.

Q: Can you share more about the impact of joining Skydeck?

A: Joining Skydeck was pivotal for us. Although Skydeck operates independently from the University of Berkeley, it provides access to the university’s vast resources. We had to articulate how we would utilize this network to propel our growth. We were very deliberate in planning our engagement with this network, aiming to leverage it to become one of the leading tech companies globally. During our time in the program, we grew from 300 to nearly 900 customers and hit the milestone of $1 million in annual recurring revenue.

Funding and Growth Metrics at Skydeck

Q: Could you clarify the funding you received from Skydeck?

A: Yes, as part of our participation in Skydeck, we received $200k in exchange for 7.5% equity in LeadSales. This arrangement is standard for Berkeley Skydeck, offering a solid foundation for startups to accelerate their growth within the program.

A Day in the Life at Skydeck

Q: What was the Skydeck program like for you?

A: Skydeck felt somewhat like going into a high performance intensive workshop for your startup, its real value depends on how actively you engage with the opportunities it presents. The program offers numerous workshops on various topics, and participation is up to you. You could be hustling non-stop or choose to benefit from these workshops and advisor sessions. We were matched with up to three advisors tailored to our specific challenges, which significantly broadened our network. The initial phase is all about goal-setting, leading up to Demo Day – a crucial event where you showcase your progress to investors. For us, reaching $1 million in ARR was a significant milestone we aimed for, greatly aided by the insights from workshops and advisors who had worked with industry giants. This experience immersed us in the Silicon Valley ethos, expanding our ambitions and perspective.

Q: How important is the environment to your growth?

A: Absolutely crucial. The physical setting of Skydeck, especially being in Berkeley and using their penthouse office with views of the Golden Gate, was incredibly inspiring. It motivates you to work tirelessly, embodying the spirit of Silicon Valley. Unlike some programs that have shifted towards a hybrid format, Skydeck’s in-person experience is irreplaceable for us. Being surrounded by that environment, where ambitious goals feel within reach, significantly accelerated our growth and ambition.

Q: Do you believe in the unique value of in-person accelerators?

A: Definitely. The in-person experience at Skydeck was transformative. Before joining, we were relatively unknown in the ecosystem. Skydeck, while perhaps under the radar, it’s at par or I’d say better than other programs in the Bay Area, like YCombinator (YC), Skydeck offers a powerful and valuable platform for growth. The connections made there, and the sheer energy of being in Silicon Valley, cannot be replicated virtually. The main difference comes in being a small batch of companies that really makes you feel special during the duration of the program. It’s an environment that fosters ambition and drive, something we deeply appreciated and capitalized on during our time there.

Comparing Skydeck to Stanford’s StartX

Q: How would you compare Skydeck to StartX at Stanford?

A: The comparison between Skydeck and StartX is like comparing apples to oranges due to their fundamentally different models. StartX, being an equity-free accelerator run as a non-profit by Stanford alumni and current students, offers a unique value proposition. Its network is incredibly valuable, featuring insights from startup luminaries like Naval Ravikant and essential fundraising resources like Ryan Breslow’s renowned book “Fundraising”. While StartX operates on a hybrid model, emphasizing remote collaboration with periodic in-person gatherings, its strength lies in the comprehensive resource library it provides. This includes thousands of documents, slides, and video workshops led by top-tier executives from Stanford, all designed to equip founders with the knowledge they need to succeed.

Q: Can you speak to the importance of being proactive within these accelerators?

A: Absolutely, the outcome of participating in any accelerator hinges on the founders’ willingness to leverage the resources and network available actively. Many founders mistakenly believe that acceptance into an accelerator guarantees success. However, without putting in the necessary work, their chances of achieving their goals are slim. Success in these programs requires a proactive approach, focusing on learning, networking, and applying the insights gained to your business.

Accessing Resources at Skydeck

Q: Are similar resources available at Skydeck?

A: Yes, Skydeck offers a wealth of resources similar to those at StartX, facilitated through a vibrant community on Slack that includes all past and present batches. Being part of Skydeck’s community allows for easy access to a wide array of resources, from recordings of previous workshops to fireside chats with prominent VCs and founders. This open environment encourages active participation, where any member can seek advice, share insights, or request specific resources. The strength of Skydeck lies in its community’s willingness to support each other, fostering a culture of continuous learning and mutual assistance.

Skydeck’s Areas for Improvement and Impact on Leadsales

Q: What could Skydeck improve on from your experience?

A: Honestly, the most challenging part for us wasn’t directly related to the program itself but rather the logistics of relocating to Berkeley. It’s incredibly expensive and finding short-term housing suitable for a six-month stay was tough. We initially landed in an Airbnb, planning to find a more permanent place within two weeks, but lucked out by meeting a local who helped us secure accommodation. This experience highlighted the need for better support in finding housing. Perhaps Skydeck could facilitate access to student residences or help connect incoming participants with housing options, especially during the summer when many students are away.

Q: Can you elaborate on the impact Skydeck had on your startup?

A: The accelerator was transformative for us, primarily through the invaluable feedback and strategic advice we received. It taught us to approach challenges smartly, not just with hard work. Our advisors and the network we engaged with at Skydeck, including the managing partner of the fund, were instrumental in helping us refine our approach and significantly advance our business. We nearly reached $1 million in ARR by leveraging both the hard work of our team and the strategic insights from our mentors. Moreover, the connections made during and after the program were crucial. Skydeck provided introductions to some of the top investment funds in the Bay Area, like Andreessen Horowitz, Founders Fund, and Sequoia. Demo Day also brought us in front of investors we wouldn’t have met otherwise, ultimately helping us secure our pre-seed and seed funding rounds. The overall experience was not just about growth in numbers but also about the strategic and network growth essential for a startup’s success.

The Ongoing Relationship with Skydeck

Q: How has your relationship with Skydeck evolved post-accelerator?

A: Our relationship with Skydeck has continued to strengthen, especially after demonstrating our commitment and growth. They even decided to invest in our seed round, which is a significant show of support and confidence in our potential. Unlike some other accelerators that may have more stringent conditions attached to their investments, Skydeck’s approach is much more founder-friendly, offering not just capital but also flexibility and trust. Their decision to follow on with an investment in our seed round speaks volumes of their belief in our vision and drive. This level of support and investment is relatively rare among accelerators and is something we highly value.

Advice for Applying to Accelerators

Q: Do you have any advice for startups looking to apply to accelerators?

A: The most critical piece of advice I can offer is to be intentional with your applications. It’s not just about applying to as many accelerators as possible and hoping for the best. That strategy shows a lack of focus and understanding of what you want to achieve. When we applied to Skydeck, we tailored our pitch specifically for them, highlighting our detailed plan for the next six months, including our focus areas for product development, sales, and fundraising. This level of detail and customization in our application made us stand out. Being intentional and showing that you genuinely want to be part of an accelerator, understanding how it aligns with your goals, is crucial. It’s about demonstrating your commitment, not just being another application in the pile. This approach will not only help you stand out but also ensure you’re applying to programs that genuinely align with your startup’s needs and goals.