The events of the past few months have only reinforced what we've always known at Roble: the most compelling opportunities come from betting on uncommon thinkers.
Take our recent investment in Holly, a software platform transforming how local governments manage their workforces. While most founders chase the familiar – MBAs building for MBAs – Holly's founders Brendan Hellweg and Cherie Chung saw an overlooked opportunity in local government services, a sector with billions in potential but largely ignored by tech.
In uncertain times, it's tempting to follow the crowd. But we're doubling down on our commitment to founders who bring fresh eyes to forgotten problems.
These are the entrepreneurs who've charted their own course and carry a chip on their shoulder – the ones determined enough to turn contrarian thinking into outsized returns. Their time will never go out of style.
As you’ll read more below, this has been a busy year for Roble and our portfolio companies. We wish you all a restorative holiday season ahead, since there’s a lot more to look forward to in 2025!
The Latest From Our Founders
PORTFOLIO NEWS AND UPDATES
Congratulations to Teachy for their $7M Series A round, led by Goodwater and Reach Capital!
We’re proud to double down on one of the most promising productivity software companies using tech to enable teachers and raise the standard of education in developing countries across the world.
Teachy has seen remarkable growth in the past year, now supporting over 1 million teachers with a suite of AI tools to improve learning outcomes for over 10 million students while reducing unpaid labor time for teachers.
All workers should benefit from AI's productivity gains, and Teachy is making sure that the world's educators aren't being left behind.
We’re also excited to announce our other recent investments:
Remyx AI is on a mission to make machine learning accessible to companies of all sizes, regardless of their in-house AI expertise. Their AI application studio streamlines the entire ML development process, from data preparation to getting models up and running.
The dynamic duo of Salma Mayorquin (CEO) and Terry Rodriguez (CTO) combines world-class technical expertise with real-world experience in building and selling ML and AI applications. Their time at Databricks, the $47B incumbent in the space, gives them unique insights into the market's needs and pain points.
Always tinkering and sharing with the developer community, Salma and Terry also run a blog called Smells Like ML, showcasing experiments and innovations in AI.
Hey, Walt! is set to transform how real estate agents track and transact with their book of business, bringing cutting-edge market intelligence and lead generation to an industry ripe for technological advancement.
This co-investment alongside M13 will help professionalize the real estate industry, enabling deskless workers in the proptech space to convert their leads and double their transactions — overcoming decades of tech debt.
CEO Mike Peregrina previously scaled the venture-backed Homie.com platform to $50M in revenue and managed over 500 residential real estate agents. This firsthand experience gives him unique insights into the pain points of real estate professionals, as well as deep industry relationships.
As previously mentioned, we’ve also invested in Holly as they empower the public sector with the workforce it deserves, starting with an AI-powered job design system that helps local governments benchmark salaries and create better roles to bring in talent.
In other portfolio news, Rising Team had their leadership offsite to celebrate their extremely successful 2024 (including an $8M Series A lead by Zeal Capital Partners and the launch of a never-before-seen AI leadership coach).
Dragonboat won the 2024 Proddy Award for ‘Top Product to Watch’, a prestigious recognition that was unveiled live at ProductCon San Francisco. This is Dragonboat’s second accolade from Product School’s Proddy Awards, which recognize the best and most innovative digital products worldwide.
UBITS partnered with Harvard Business Publishing to gather data for a report on corporate learning and development in Latin America. Insights from the incoming report will impact the future of business training in LATAM.
Lens Into a Human-Enabled Future
THOUGHT LEADERSHIP HIGHLIGHTS
Our latest addition to our blog examines how AI startups can get their “foot in the door” with enterprise customers with training tools that optimize onboarding as well as continue to provide contextual insights as a workflow co-pilot – like being able to take your coach out on the field with you.
You can read the full post here.
David traveled to New York to attend the Culture Shifting Summit, a deal-making event that seeks to narrow the inequality gap in venture capital by gathering a coalition of prominent Black and Latino investors.
“It was inspiring to be amongst LPs and GPs who share this vision,” he wrote. “As we enter an exciting time to build new technology companies, we share the belief that next-generation unicorn companies will reflect the broader demographics of the US, and we are excited to actively collaborate to make that a reality.”
David also joined the Board of the Latinx MBA Association, the largest organization of Latino professionals (with over 2k members) from top 50 U.S. MBA programs. They are currently in the midst of planning for their 2025 Annual Summit.
Sergio attended both the RAISE Global 2024 Summit and Affinity’s Campfire conference, where he had the opportunity to share our VC OS with representatives from the CRM’s over 3,000 customers across the financial services industry.
Emily mingled with many successful founders at a venture & startup gala hosted by VC in DC and Halcyon House, then Sergio joined Emily in DC for Zeal Capital Partners’ AGM, which focused on reimagining work, wealth, and wellness.
What Keeps Us Up at Night
KEY RISK FACTORS
By Sergio Monsalve
As we look ahead towards what to expect in 2025, I wanted to continue the thread on uncommon thinkers we started in the intro to this newsletter. Their diversity of thought and experiences are useful to VCs to determine the grit they’d bring to the level of selling and scaling that’s required to make it past the seed stage.
The 3 flavors of “uncommon thinkers” we believe are the best-positioned to succeed in the early stage:
- You’re a user of their own product, or built it for yourself.
Ex: Becky Flint built Dragonboat, a product operations platform, and has scaled it to Series A after working as the Product Lead for POS and Demand Gen at PayPal. - You find your customer and tinker until it really works for them.
Ex: Sai and Atul pivoted Hyperbound from an email customization copilot into a full-blown AI chatbot coach for SDRs, sharing their iterations, learnings, and momentum with their online following — and are now looking at over $1M ARR in little under a year. - You were selling to your customer and were frustrated by how inefficient it was.
Ex: Salma Mayorquin was a Databricks machine learning engineer and data scientist who learned the unique pain points of the developer community while working at Databricks for over 2 years; she recently closed her pre-seed round for Remyx (a platform for custom AI models) led by us and Alchemist.
As advantageous as this orthogonal thinking can be, each one comes with their own potential shortcomings:
- You’re too enamored with your own idea. The enthusiasm and passion is there, but you still need to go out and get validation that others in your space actually need what you see as the solution. Our founders counteracted this by landing anchor customers who were willing to experiment with them.
- You need to work harder for customer empathy. You may have to dig a little deeper to really understand the heart of your customer’s problem, and what would get them to really use your solution. You haven’t done your customer’s job day in and day out, so make sure you have a robust [source of truth] that helps you get inside their shoes. As mentioned during our brand webinar earlier this year, Hyperbound co-founders Sriharsha and Atul counteracted this by doing months of research into their target customer before making their first LinkedIn post.
- Creating something too adjacent can be easily copied by the incumbent they’re trying to complement. This one is pretty self-explanatory, and is always a risk for early-stage SaaS. You can mitigate this by becoming cozy with the incumbents and/or gather intel on what they’re focused on, which can often be done even by looking at their job boards and hiring needs; if they’re looking for engineers and product people in your space, they are likely building your competition. Lastly, you should also be an active “secret shopper”, getting their sales teams to tell you about new features they have coming soon.
Even if you’re an uncommon thinker, you should be on the lookout for these potential blindspots, and the VCs you talk to should have an open mind about some of the more uncommon problems you may be trying to solve.
What Caught Our Attention
NEWS AND RESOURCES
Generative AI, the American worker, and the future of work (Brookings)
Services as software, executing on the 4.6T opportunity (LinkedIn)
Insights for founders:
- Position at the interface where data is born
- Target labor budgets, not software budgets
- Look for labor market arbitrage
- Build for work humans never did
ServiceTitan S-1 Breakdown (Tanay’s Newsletter) – Great $5.2B IPO in the future of work theme; seems like AI will create many opportunities here given the specialization of the models. ~David
About the author
Roble Ventures is a future-of-work focused fund investing in technologies that enable people, teams, and organizations to achieve their most ambitious work.
