For 14+ years, we’ve invested in unicorns like Lyft, Wish, Gusto, and Scale at the earliest stages. Watch our April 4th Outlander Spring Showcase to meet 5 of our current early-stage portfolio companies: Crow Industries, HavocAI, Lula Convenience, Skyways, and Tryby!

Here’s an overview the lineup:

Crow Industries 

🎯 autonomy, ML/AI, robotics 📍 Scottsdale, Arizona
🎙 James Crowell, CEO + Founder 📧

Crow Industries (CI) is a full-stack autonomy startup focused on developing cognitive heavy equipment for the mining industry.

The mining industry is experiencing major production shortages due to a growing labor crisis, precisely when production of critical minerals must dramatically increase to keep pace with the Clean Energy Transition. CI is working to close this labor gap by creating fully autonomous fleets for mine operators that go far beyond the automated equipment utilized today. Rather than one person operating one machine, CI’s solution will allow one person to supervise hundreds of machines at multiple sites, monitoring for problems that may arise in real time. The company successfully completed the Techstars Industries of the Future accelerator last summer, Outlander VC led their PreSeed in the Fall, and Winklevoss Capital joined the round soon after.

Best Outlander VC value-add: Working closely with the Outlander team to optimize our internal business structure and push closer to solving customer problems in the market has been invaluable.

Best advice from Team Outlander: Too many to count! One that stands out is to be relentless in pursuing customer solutions while demonstrating outsized value-add.


🎯 maritime autonomy, USVs, attritible 📍 Providence, RI
🎙 Timothy Rhatigan, CEO + Co-founder 📧

HavocAI is a scalable maritime autonomy startup focused on bringing low-cost, high-rate production sUSVs (small Uncrewed Surface Vessels) to the defense and commercial markets by early 2025.

Leveraging the latest in robotics and controls software and combined with established low-cost, high-volume advanced maritime manufacturing processes, HavocAI, through its proprietary HavocOS and HavocCloud, enables large force autonomous USV operations, built an order of magnitude cheaper per unit and within OSD Replicator’s stated goal of acquiring and operating 1000s of attritible unmanned assets within the next 18-24 months. HavocAI’s mission, shaped by real-world operations in the Black Sea, Red Sea, and growing threat(s) in the Indo-Pacfic, is to prove autonomous maritime operations at scale by the end of 2024 – to both ‘control the chaos and wreak havoc’ on our adversaries.

Best Outlander VC value-add: Outlander VC is the ideal early investor and partner for HavocAI – they understand the importance of moving aggressively, even audaciously, fast to market and have authentically supported our efforts here since our earliest days.

Best advice from Team Outlander: Expect the unexpected and be ever vigilant with early burn because the $$$ will go faster than we think.

Lula Convenience 

🎯 SaaS-enabled marketplace 📍 Philadelphia, PA
🎙 Adit Gupta, Co-founder & CEO 📧

Lula Convenience helps retailers through their digital transformation journey. Whether that’s getting a store or chain of stores onto all online delivery, pickup, catering, or helping them launch their own website, Lula is the one-stop shop vertical saas solution trusted by several thousand retail locations across the United States.

Best Outlander VC value-add: Access to an incredible network & candid feedback available 24/7. 

Best advice from Team Outlander: It’s vital to keep burn low, and while most founders decide to increase burn, they often forget to cut unhealthy fat – something you need to think about every single day (not once a year).


🎯 autonomy, AI, aerospace, drone 📍 Austin, TX
🎙 Charles Acknin, CEO + Founder 📧 

Skyways is creating a new form of transportation to advance our civilization. Starting with fully autonomous cargo drones sold to DoD and B2B commercial markets, Skyways drones allow transportation of parts to complex or dangerous places. Once we operate for our customers with thousands of aircraft at scale, we will then build a larger aircraft to transport people and address traffic congestion issues. Ultimately, we want to become the world’s largest airline and completely rethink how we move cargo and go places.

Best Outlander VC value-add: Proactive and moves fast when needed.

Best advice from Team Outlander: When in doubt, there’s no doubt — fire people immediately.


🎯 AI, SaaS, Voice, AI Agents 📍 New York City, NY
🎙 Michael Woo, CEO + Co-founder 📧

Tryby AI is building hyper-realistic, advanced conversational AI for businesses that answer and execute on 100% of calls, 24/7. Today, businesses struggle to maximize revenue from leads and spend hours each week on repetitive responses & actions. We help our customers provide exceptional service to their customers with AI, growing their revenue while saving their teams hours on daily tasks with our conversational AI and AI agents.

Best Outlander VC value-add: Exceptional partners who care for you.  Foster growth through the extensive Outlander network and provide insightful feedback throughout the startup journey at any point and time.

Best advice from Team Outlander: Move fast, keep an open mind, and pivot fast if needed. I appreciate not only the advice but also the confidence and support Outlander provides to founders to execute on ambitious, ambiguous, but promising problems and tech.

Register for the Outlander Spring Showcase for asynchronous access to decks, pitches, and to learn more about these game-changing startups! Meet the rest of our portfolio here.

Welcome to Venture Visionaries, a brand-new series brought to you by Outlander VC. Hosted by Paige Craig, Managing Partner at Outlander VC, this series explores what sets these investors apart and provides unique insights into their perspectives on the startup world. Join us as we sit down with some of the most influential investors in the industry, uncovering the secrets behind their success and learning how they navigate the ever-changing landscape of investing. 

From their investment strategies to their predictions for the future, we’ll bring you inspiring conversations that’ll resonate with aspiring entrepreneurs and anyone curious about the world of venture capital. So, grab your headphones and get ready to be inspired by the visionaries shaping the future of innovation! 

First up, we have Mike Maples, Jr. from Floodgate! Mike is a renowned venture capitalist known for his keen eye for breakthrough startups and his ability to identify successful founders. We’ll dive deep into the key characteristics that make founders successful and the traits that set breakthrough startups apart from the rest. Mike will also share his insights on the role of an investor as a co-conspirator, working closely with founders to drive their success. In our conversation, we cover: 

If you’re ready to dive in, listen to our full conversation now to hear Mike’s thoughts on successful founders, breakthrough startups, and the future of venture capital. Alternatively, keep scrolling to discover our three biggest takeaways from the episode, key quotes from Mike, and more exciting content below. 👇

Takeaway 1: Invest in pattern breakers, not pattern matchers

In our conversation, Mike Maples, Jr. emphasized his investment philosophy of backing pattern breakers—individuals who propose a new way of doing things which challenges the status quo. He believes that a great startup forces a choice, not a comparison, and is essentially a challenge to the established norms.

“My job is to invest in pattern breakers,” Maples stated. “A lot of people say that venture capital is about pattern matching, and I actually somewhat reject that. My job is to find the people who propose a new way and say, hey, the way that you’re used to doing things isn’t the best way. There’s this radically different way.”

He further explained, “The pattern breaker engages in pattern breaking thinking, the pattern breaking actions.” Maples believes the pattern breakers are distinguished by their thoughts and actions, often acting in ways that make others uncomfortable, but leading to innovation and change.

Takeaway 2: Inflections are vital to startup success

According to Mike, inflections play a critical role in a startup’s success. He believes that a powerful inflection point is a precondition for success in a startup, as it provides them with the ability to wage asymmetric warfare on the present.

“I look for, on the ideas front, are they harnessing inflections?” Maples said. “An inflection is kind of like a surfer has to have skill, but they have to pick the right wave. And a good wave is a precondition for success at surfing. And I believe that a powerful inflection is a precondition of success in a startup,” he explained.

He also emphasized that timing is a significant risk factor, and thus, understanding inflections can help in evaluating whether an idea is well-timed or not.

Takeaway 3: Influence of AI and digitization on future startups and businesses

Maples shared his fascination with the rapid advancements in generative AI and its potential implications on various industries. He also discussed the concept of “digital twinning,” where a product’s usage and potential issues are simulated and tested in the digital domain before being built in the physical world.

“The thing I find interesting about AI is there’s so many inflections and they’re happening so quickly and they’re so unpredictable that one thing displaces the next thing from one week to the next,” Maples said.

“It’s not how I would have normally thought about things in the past,” he said, discussing digital twinning. He added, “You start to wonder if more and more products will have a digital twin that is specified, and then that digital twin will simulate lots of different corner cases.”

Key quotes

Meet Mike Maples, Jr.

Mike Maples, Jr. is a co-founding Partner at Floodgate. He has been on the Forbes Midas List eight times in the last decade and was also named a “Rising Star” by FORTUNE and profiled by Harvard Business School for his lifetime contributions to entrepreneurship. 

Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.) Some of Mike’s investments include Twitter,, Clover Health, Okta, Outreach, ngmoco, Chegg, Bazaarvoice, and Demandforce.

Mike is known for coining the term “Thunder Lizards,” which is a metaphor derived from Godzilla that describes the tiny number of truly exceptional companies that are wildly disruptive capitalist mutations. Mike likes to think of himself as a hunter of the “atomic eggs” that beget these companies.

Mike is the host of the Starting Greatness podcast, which shares startup lessons from the super performers.

I have been investing in AI startups for most of the last decade. AI startups have been hot recently, with a reported $75 billion invested in the space in 2020 alone. In 2016, however, getting investors to take AI seriously was no small feat. Then, AI felt like something from Star Trek, and while the ideas were fascinating, many investors wondered, “How will you make money?” Admittedly, it is hard to predict how foundational technologies will create value but I’ve always hedged my bets on exceptional founders first and foremost, which is what led me to write first checks into two AI unicorns back in 2016.

When I was introduced to the Scale AI and Imbue founders, they were purely in the idea stage: pre-product and pre-business model. That year alone, I’d received hundreds of AI startup decks, investing in only five or so. Of those handful of AI bets, only these two grew to multi-billion dollar companies. In both instances, it was all about investing in the right founders, then helping them find the right vertical. 

From recruitment tech to Imbue: 

In January 2016, I was introduced to the founders of Imbue. Formerly known as Sourceress, they were building an AI tool to source candidates for recruitment efforts, match those candidates with open roles, and send personalized outreach to schedule initial interviews. From our first call, the founders were exceptionally smart, curious, and customer-driven, jotting down notes from our discussion on how to build a successful brand. There was no fundraising deck, but only three months into building the business, they’d already acquired customers, proven initial interest, and were poised to solve a massive problem using AI.

By February 2016, we became their first investors, investing $500k at $4.8M Cap. Over the next five years, I introduced the founders to potential customers and met with them for monthly brainstorms, especially as they worked through their pivot in 2019. While the initial focus on recruitment had already evolved into sales, their pivot to an AI with more generalized intelligence was the key to their success. With this broader scope, Imbue has created a fundamental technology that will change the world. With its latest $200M in Series B funding and $1.5B valuation, Imbue’s primary mission is to drive the development of AI systems capable of advanced reasoning and coding. The company is poised to create practical AI agents capable of accomplishing substantial tasks while maintaining safety in real-world applications.

One of the few women-led AI unicorns, Imbue co-founder Kanjun Qiu is really excited about “how can we make that accessible to everyone so that everyone can imbue intelligence and be able to use that intelligence.”

From medical matchmaking tech to Scale AI: 

Back in April 2016, Scale AI co-founder Lucy Guo reached out to me on Twitter, pitching the first iteration of Scale AI. Initially, they were building a tool to help millennials find medical professionals with the unique idea of rating specialists by specific tasks/procedures versus a generic rating. While I wasn’t 100% sold on the product/market, I was beyond impressed with the founders. Both Lucy Guo and Alexandr Wang are hands-on, driven, brilliant, and possess the kind of locus of control and communication skills that inspire others to join their teams, help them succeed, and invest in their vision. In every conversation with Lucy, she is unfaltering in her creative problem-solving and unafraid to experiment and adjust until something finally works. These things were true in 2016 and remain true today, which is why our #1 investment criterion is always the founding team.

Two months later, Lucy reached out with their latest pivot, the Scale API: “With just one line of code, you can deploy a human on-demand to do tasks such as content moderation, data extraction, appointment scheduling, and more!” I immediately wrote back to tell her this pivot was critical and that they should drop everything else and run with it. With their exceptional Founder Framework scores, I knew they could build something big and had the grit to pivot as needed. So, in August of 2016, I invested $150k SAFE on a $3M cap in what is now Scale AI, the $7.3B AI unicorn; and then reinvested months later when they raised a much larger seed round. 

Most recently, co-founder Alexandr Wang was recently named one of the top 100 Most Influential People in AI and spoke at the White House on the risks of AI, while Lucy Guo has joined our portfolio a second time with her latest venture: Passes.

Now that AI has become crowded with everyone on the hunt for their AI unicorn, I take a slightly different investment approach. I still look for the right founders and the right vertical, but I take a more nuanced approach looking for niche, verticalized applications of AI largely within SMB, enterprise, industrial and government applications. 

A few examples below:

Coco Delivery – AI for Enterprise Logistics

Coco Delivery has married robotics with AI to augment its human workforce. Coco’s robot delivery fleet is driven remotely by humans plus an AI co-pilot. Learning from the human drivers, the AI co-pilot is initially used to augment the human driver, quickly reacting to obstacles, monitoring speed, etc. Eventually, the AI co-pilot will replace the need for a human driver piloting every delivery, elevating the human workers to oversee fleets of robots. 

Fabi – AI for Data Science

Fabi is leveraging AI and natural language processing (NLP) to democratize data insights. Fabi’s AI enables seamless communication with datasets for non-technical teams, empowering them to extract meaningful insights independently. Likewise, leveraging Fabi’s AI enhances the efficiency of data science teams by transforming the way they analyze data and providing advanced tools for analysis. Fabi’s application of AI ultimately fosters a more collaborative and productive data-driven decision-making process across many industries. 

Skyways – AI for Drone Navigation

Skyways is a company at the forefront of advancing drone technology. In addition to their innovations in aviation, Skyways is leveraging AI to overcome traditional limitations and enhance the autonomy of drones. Skyways’ cutting-edge AI technology allows drones to navigate and operate seamlessly even in areas where GPS signals are unreliable or unavailable. This technology has significant implications for various industries, opening up new possibilities for autonomous drone applications in challenging and complex environments.


Barometer – AI for Brand Safety

Barometer leverages advanced artificial intelligence to enhance brand safety and contextual targeting in the realm of podcasts. Their innovative approach involves machine learning algorithms to analyze and understand podcast content, ensuring that advertisers can maintain a safe and contextually relevant environment for their brands. This innovative approach allows major brands to ensure their advertising is aligned with values in a rapidly growing podcast space.

Crow Industries – AI for Mining Operations

Crow Industries (CI) is building the Robotic Labor Force of the mining industry, creating autonomy for heavy equipment and underground operations. CI’s initial product enables the mapping of mines 10X faster than traditional methods, while simultaneously collecting real-world training data for the autonomous models. CI’s robotic solutions are addressing the ever-growing need for safe and reliable labor as the mining industry rapidly continues to grow.

Vidrovr – AI for Video Analytics

Vidrovr uses patented AI and multimodal machine learning algorithms to understand video like a human would, and then helps businesses make smart, efficient, and profitable decisions based on the information in video. Vidrovr is revolutionizing an outdated and arduous process of data collection, analysis, and instrumentation by bringing the task to the physical world through video analysis. Today their system is driving efficiency for leading federal and private sector companies.

Within AI, we are particularly focused on startups using this formula: 1) a gritty, complicated, or mundane job that usually requires a human worker to be on-site somewhere to do the job, plus 2) AI that learns from that human worker until it can do the labor intensive/repetitive or complicated tasks at a faster, more efficient rate. AI’s ability to extend a person’s capabilities will revolutionize how we work and live, and that’s where I’ve always loved to invest.

For 14+ years, we’ve been investing in unicorns like Lyft, Wish, Gusto, and Scale at the earliest stages. Now, meet 5 of our current early-stage portfolio companies that presented at our 2023 Outlander Fall Showcase

From innovations in AI/ML in computer vision, Mar/AdTech in consumer product sampling, future of work via flexible talent marketplaces, paid membership and SMB community building, and e-commerce and API for B2B equipment rentals, these companies are building the future of everything:


🎯 SaaS, B2B, rental, e-commerce 📍 Atlanta, GA
🎙 Donald Boone, Co-founder & CEO 📧

BoxedUp is a subscription-based software that allows equipment rental companies to set up online stores quickly. Founded by three Amazon alum, the company uses APIs and a set of rental-specific features to streamline equipment quoting, logistics, and inventory management so that B2B suppliers can grow their operations. In just 3-months, the company has amassed more than $20M of contracts with suppliers in industrial equipment and motion-picture categories.

Best Outlander VC value-add: Experienced team, access to successful founders and investors, and a robust network.

Best advice from Team Outlander: Find a problem in an underserved market that you’re uniquely qualified to solve, build a solution for an underserved customer group, and grow it from there.


🎯 SaaS, paid membership, virtual community 📍 Atlanta, GA
🎙 Murtaza Mambot, Co-founder & CEO 📧

Heartbeat is an all-in-one SAAS platform for managing large communities for SMBS digitally. People are tired of duct-taping Slack + Notion + PayPal together, and we do it all in one platform & give them the tools to scale engagement and revenue fast (i.e. subscription management, upsells, affiliate tracking & payouts). They often make 3x revenue in 6 months.

Best Outlander VC value-add: he fundraising assistance is huge — They secured 70 meetings in 2 weeks to close out follow-on capital for our pre-seed round. All incredible investors & many of them we never dreamed of ever getting meetings with. 

Honestly, the thing I’m most grateful for, though, is the day-to-day operating advice. Leura has helped a TON with key strategic decisions — and doing that together for months & months has massively helped us fine-tune our own product sense & build something really meaningful. She constantly pushes us to challenge our assumptions & think more strategically, given the limited resources we have as a startup, and we are so, SO much better for it.

Best advice from Team Outlander: What to prioritize while building a product. We get hundreds of feature requests from our customers, but our focus is always on prioritizing features that over 50% of users will immediately use and either grow revenue or improve stickiness. Everything else is secondary.


🎯 future of work, marketplace 📍 Miami, FL
🎙 Michael Saloio, Co-founder & CEO 📧

Huddle is a market network where founders can reserve time with flexible teams of expert designers and builders. Today, we’re an elastic workforce that makes it easy for startups to hire fast and flexibly, where you can post a project and start with your team in under a week. Our network is a highly vetted community of ~1k builders from companies like Square, Spotify, Amazon, and more. In the future, we will be the online HQ for the most in-demand workers in the world.

Best Outlander VC value-add: Fundraising and talent support (in areas beyond technical talent) and advice from seasoned founders and investors.

Best advice from Team Outlander: Paige and Leura’s advice all seems aligned with one key theme. In my own words, I’d summarize it as: “Swing BIG, stay scrappy.”

Strapt Vending 

🎯 IoT, MarTech, AdTech 📍 Atlanta, GA
🎙 Carly Simenauer, Founder & CEO 📧

Strapt is reimagining CPG marketing through experiential, automated, and data-driven product sampling. Through their innovative service model, Strapt has identified a uniquely scalable approach to vending that offers CPGs their first opportunity to get products into consumers’ hands at the exact point of need, all while driving measurable traffic, conversions, and upsell opportunities for their partners.

Best Outlander VC value-add: Outlander’s network seems endless. Whether investors, customers, mentors, or otherwise, Outlander always seems able to connect me to the right person at the right time.

Best advice from Team Outlander: Stay focused on the vision. As an early-stage company, there are endless ways to grow and scale. Team Outlander has helped me identify and adopt (or disregard) strategies and opportunities that keep me laser-focused on realizing our vision.


🎯 AI, ML, computer vision, enterprise software 📍 New York City, NY
🎙 Joe Ellis, Co-founder & CEO 📧

Vidrovr transforms video data into knowledge for enterprise and federal leaders. Our patented and proprietary machine learning technology unearths the mission-critical insights hidden in messy, unstructured video data sources like social media, terrestrial cameras, live television, aerial footage, and beyond. Our platform will help you transform video data into knowledge whether you’re a major broadcaster analyzing how guest appearances impact TV ratings, an airfield evaluating the safety of a plane live plane landing, or a DoD analyst reviewing thousands of hours of video to determine movement patterns. Vidrovr is the key to unlocking the information decision-makers need to drive revenue, lead strategically, and automate monotonous processes. To date, Vidrovr has analyzed over 25 billion frames and monitored over 2700 unique data feeds for organizations such as the US Air Force, State Department, DARPA, Associated Press, and many other enterprises. 

Best Outlander VC value-add: Too many to name! We’ve hired folks directly from Outlander referrals, which has been a major value-add.  The team is never afraid to dive deep with you and get into the nitty gritty details of solving a problem. Finally, they’ll always give you their honest assessment of where you’re succeeding and where you need to improve. 

Best advice from Team Outlander: We lost a candidate due to our offer process and some inefficiencies that we had. The team helped us revamp how we communicate offers. We haven’t lost a candidate we’ve given an offer to since that advice.

Watch the replay of the Outlander Fall Showcase to learn more about these game-changing startups! Meet the rest of our portfolio here.

Over the last 15 years, I’ve funded visionary founders building everything from robot delivery fleets to web3 creator economies and everything in between. Excited as I was by every new venture, I quickly realized that—like our founders—expertise in every moving piece of the now 150+ investments was impossible and tactical advice was not Outlander VC’s role to fill. So instead, we learned to ask the right questions to support our founders in forging their way into the unknown.  

First and foremost, founders must identify their startup’s North Star Metric, i.e., the #1 most important metric in the business. Then, build a plan that ladders up to their target NSM, including sub-goals like product roadmaps, hiring plans, operational optimizations, sales/marketing strategies, etc. Learn more about defining your North Star Metrics here

With a target North Star Metric and plan in place, here are the seven key support questions we ask our portfolio founders to ensure they prioritize their startup’s success:

First, establish the financial baseline:

  1. What’s your monthly burn and current runway? Burn and runway will impact how to prioritize every subsequent element of the business. As such, we always ask this question first to establish the baseline health of the company and to contextualize the appropriate priority and timeline for the following questions.
  2. What goals do you need to achieve to raise your next round? Do you have the runway to achieve those goals? Building on #1, founders should always be laying the foundation for their next raise. By establishing what must be accomplished before the next round, founders can adjust their short-term targets to reach their North Star Metric and burn accordingly. 
  3. Are you being realistic about your financials? By starting with these baseline financial questions, we can help founders prioritize where their efforts will be most impactful and build long-term success. For example, while “always be fundraising” would be ideal, we recommend founders allow for six months (minimum of four) to fundraise and close capital. Checking in with #1 and #2 lets both the founders and our team better plan for their next raise.

Second, assess operational highs & lows:

  1. What problems are keeping you up at night? This is a great question to gauge not only where the most energy is being spent but also if solving this problem aligns with achieving the startup’s North Star Metric. Once you contextualize pain points within long-term goals, it’s easier to prioritize each problem against your North Star Metric strategy.
  2. Are you on track to achieve your target North Star Metric? Do your “wins” support your target NSM? Not all “wins” are created equal. Keep the conversation focused on how each win drives their target North Star Metric. Things aren’t “working” if they haven’t launched, just launched, or haven’t dramatically moved toward their target NSM. For early-stage startups, we are looking for big wins that demonstrate traction, not minor optimizations.

Finally, asses team performance:

  1. How is the current team doing across character, work ethic, and results? One of the most common founder pitfalls is hesitation around firing “bad fits.” To keep this front of mind, founders should regularly assess each team member’s work ethic, performance, and character, too. While deliberating if the situation is “bad enough,” an ineffective or inconsistent team member can make or break your startup’s success.
  2. How is the team evolving? Are you finding the right people to bring on? On the flip side of #6, scaling your startup will require growing your team, too. Hiring is another pain point that can hinder a startup’s ability to scale, and a founder who cannot inspire others to join them indicates they may need additional support from our team. 

Much like the parable of teaching a man to fish, the best way to support your portfolio companies is not by prescribing tactical advice. Instead, asking these seven key support questions at least once a month trains founders to keep them front of mind as they prioritize their team’s efforts to maximize their startup’s success.

For 14+ years, we’ve perfected investing in unicorns like Lyft, Wish, Gusto, and Scale at the earliest stages. Now, meet 5 of our current early-stage portfolio companies who pitched at the Outlander Spring Showcase

From innovations in robotic automations in hospitality, fintech marketplaces for investing in VC funds, no-code productivity and compliance platform  for field data, B2B manufacturing marketplaces, consumer health tech for care data tracking, these companies are building the future of everything:


SaaS, automation, ecosystem

Backbar is automating the creation of complex beverages like cocktails, mocktails, coffees, superfood juices, and more. We’re solving for increasing cost pressures, labor shortages/turnover, and lacking guest experience by creating an end-to-end beverage platform. We’re going to make a 3-5% margin improvement in an industry where $70 billion is spent every month.

Based in San Diego, CA, co-founder and CEO Rishabh Kewalramani is laser-focused on optimizing hospitality’s highest-margin product, beverages, with the largest innovation in decades through BackBar.



SaaS, mobile-first, future of work

At Eskuad, it’s our mission to help natural resource squads save time and resources by providing access to our platform anywhere and anytime, regardless of internet connectivity. Eskuad’s platform makes it easy to digitize old-school paper forms as well as automate data collection like GPS information, direct upload photos, and automated reporting. Designed for field operators that operate in Natural Resources and Environmental related companies, Eskuad is connecting the disconnected and building the future of field work.

Based in Atlanta, GA, founder and CEO Max Echeverria is committed with simplifying and streamlining field work with no-code productivity and compliance technology through Eskuad.



SaaS, enterprise, manufacturing, marketplace

Made is a B2B marketplace platform that solves points of friction between aerospace and defense manufacturers and US-based suppliers. We focus on cutting down lead times with fast quoting, superior ERP tooling, and a robust marketplace of suppliers building the highest quality goods for the toughest environments.

Based in Boulder, CO, founder and CEO William Allen is obsessed with building a B2B marketplace platform for manufacturers to meet and work with suppliers through Made.



health tech, care economy, IoT, SaaS

Talli is a modular, configurable platform of software and hardware options designed to take the work out of capturing daily care and health information across the $648B care economy. We started with babies because that’s where the Talli story began. We’ve done $1.1M in revenue in the baby market with 16k MAU and 30M events logged. We grew our revenues by almost 400% from 2021 to 2022 and our SaaS revenue is growing an average of 36% per month since launch. Now, we’re expanding into senior care as well. After making our platform fully configurable in the summer of 2022, we started seeing customers buying our baby product and adapting it for care of their aging parents. Even before releasing a configuration marketed for elder care, we had more than 500 users in our database logging for someone over the age of 60. We’re releasing our Talli Care configuration for senior care and chronic conditions on March 22nd.

Based in Atlanta, GA, founder and CEO Lauren Longo is disrupting consumer health tech with a flexible, a la carte platform of software and hardware options for simple tracking of daily care and health information through Talli.



fintech, wealth management, marketplace, AI

Velvet makes it easy for institutional investors to discover, evaluate, and invest in private funds. The traditional process is tedious, difficult, and expensive. We’re here to make private funds simple and transparent. We save investors time by listing funds at scale, automating diligence, and simplifying the investment process. Velvet helps you easily discover funds, connect with managers, evaluate track records, and make investments on behalf of clients or yourself. Velvet curates hedge funds, venture capital, private credit, and private equity at scale. Our listing platform makes it easy to find pre-vetted funds based on mandates, categories, fund types, asset exposure, size, returns, and more.

Based in Salt Lake City, UT, co-founder and CEO Andrew Pignanelli is obsessed with building the future of private finance through Velvet.


Watch the replay of the Outlander Spring Showcase to learn more about these game-changing startups! Meet the rest of our portfolio here.

In the last few years, Atlanta has birthed several multi-billion dollar tech companies, including SalesLoft, Calendly, and Rubicon just to name a few. But now, we are sitting at a critical crossroads in terms of our city’s future leaders.

So, I’m reaching out to you—our network of outlanders from Los Angeles, New York, DC, Miami, and across the country—to help us elect a mayor who will have a profound impact on the most diverse startup city in America.

Atlanta needs an ethical, progressive mayor who wants to engage with the startup and venture community, and Andre Dickens has impressed me since day one. That’s why I’m hosting a critical fireside chat with Andre on 11/18 at 11 am ET, so you can see for yourself why he’s the right candidate for the job.

Even if you are not an Atlanta voter, consider this: Elections—like startups —require capital to succeed. But unlike state elections, the benefits of diverse startup hubs like Atlanta extends beyond state and even country lines.

With a donation as small as $1,000 (and as large as $4,300), you can invest in the leadership necessary to build the next Atlanta unicorns and the future of diverse emerging managers and founders alike. Leura and I are maxing out our individual donations to support his campaign, and we are asking our friends and family to join us in supporting the future of Atlanta innovation through a contribution to his campaign, too. 

If you are an Atlanta voter and believe our city deserves an ethical, progressive mayor, look no further than Andre Dickens.

At our fireside, we will dive into his plans to advance education, build bridges with the startup and investment community, and provide a safe, efficient, and ethical local government. I believe that for the future of our startup ecosystem and the health and safety of our great city, he is the right person for the job.

Hope to see you all there!

— Paige

Up next: OutPitch 2.0

5 finalists. 1 virtual stage. $100,000 investment on the line. 🏆

Calling all innovative early-stage tech startups in the United States:

If you’ve got what it takes to outvision, outbrave, outperform, outsmart, and outpitch the competition, start your OutPitch 2.0 application now! The winner of the $100,000 investment from Outlander VC will be chosen from the five finalists who pitch live on December 7, 2021.

APPLY x OutPitch.20

Attendees are invited to join us virtually on December 7, 2021 at 5 pm ET to watch the five OutPitch finalists pitch live for a chance to win a $100,000 Outlander VC investment. Spots are limited, so save your seat now!

In celebration of Outlander’s first birthday 🎂, we’re hosting another Outlander Demo Day on September 30, 2021, where you can meet five of the game-changing companies and visionary founders we’ve invested in since our September 2020 launch! For your convenience, there are two ways to celebrate with us:

  1. Register now and join us virtually on 9/30 to participate in the live audience Q&A with the presenting companies.
  2. Register now and watch the event recording at your own leisure!

The recording of Outlander Demo Day will be available to all registrants immediately afterward here, so either way, register now! You do not want to miss these pitches.

From innovations in Video Robotic Process Automation (vRPA) and machine learning, consumer health and care data tracking, and SaaS-enabled marketplaces to shop local, build your next startup dream team, or find inclusive transportation, here’s a sneak peek of the magic to come at Outlander Demo Day:

City Shoppe — SaaS-enabled marketplace powered by local small businesses and values-based consumers.

City Shoppe’s SaaS-enabled marketplace is an interconnected platform bridging the gap between local businesses and modern consumers. On the business side, we manage and build SMB’s business behind the scenes, allowing them to just focus on product curation. The consumer side is our one-stop-shop marketplace that exceeds the expectations of the next generation of consumers by enabling them to shop ethically, filter by values, empower local vendors, and change the world. City Shoppe is the future of  “Think Local First.”

You may recognize City Shoppe as the winner of OutPitch 2021! Based in Austin, TX, founder and CEO Ash Cintas is laser-focused on creating a SaaS-enabled marketplace that empowers anyone to shop locally from anywhere through City Shoppe.

Huddle — where freelancers invest in startups with their time + startups scale in exchange for equity or cash.

At Huddle, we get that finding talented people to work on your startup is hard. After spending an average of 3-6 months fundraising, founders spend an additional 3-months putting their team together. That’s why we build Huddle: a social marketplace that connects the world’s top startup builders to founders. Founders pitch the Huddle community on what they’re building and need help with (pitch deck, mobile app, new brand, etc). Huddle’s platform matches startups with flexible, super teams that can move fast and be paid in cash and equity, meaning no more wasted time scrolling freelance marketplaces and interviewing expensive agencies. 

Based in Miami, FL, co-founder and Chief Product Officer Stephanie Golik is obsessed with increasing entrepreneurship and creator ownership via the FinTech, AI, blockchain, and creator economy marketplace that culminates to Huddle.

MedHaul — enabling safe, reliable, and efficient transportation for patients with unique needs.

Access to transportation can mean the difference between chronically ill patients safely managing their health at home or missed treatments and costly unnecessary visits to an emergency room, and MedHaul is here to close that transportation gap. We serve as a conduit between multiple communities—healthcare providers, transportation workers, and underserved populations—creating a unique solution that empowers the entire community to better health. MedHaul’s technology makes it easy for healthcare providers to find and book rides for their most vulnerable patients, regardless of their unique needs. Through our streamlined transportation platform, we help healthcare workers save time, reduce costs, and improve patient satisfaction while closing critical transportation gaps for those who are impacted most. 

Based out of Memphis, TN, founder and CEO Erica Plybeah is committed to providing safe, cost-effective, and reliable healthcare transportation for all through MedHaul.

Talli — hardware + software solution for one-touch, mobile, hands-free logging of health and care data.

Our mission at Talli® is to reduce the mental burden of caregiving through easier logging of care and health data. Our flexible IoT platform provides hardware and software options for one-touch, mobile, and hands-free logging across infant care, senior care, and home health markets. Talli is flexible enough to track any type of event and then translate that data into actionable information and the insights you need most.

Based in Atlanta, GA, co-founder Lauren Longo is disrupting the tracking and sharing of health and care data through an IoT logging and health data platform with configurable hardware and software solutions through Talli.

Vidrovr — video analysis platform for indexing and activating video content to create vRPA workflows.

Vidrovr enables users to index live and archival video content, access embedded video data, and use their video data to create Video Robotic Process Automation (vRPA) workflows. Our platform unlocks the untapped potential of a  company’s unstructured data within video, audio, and image assets, then translates those data points into actionable business insights. As a result, we leverage video data to modernize industries dependent on physical operations in ways never thought possible! Vidrovr’s AI localizes the complex interactions between people, objects, and events within video data and then creates insights on improving safety, simplifying compliance, and streamline logistics. Simply put: At Vidrvor, we make videos as searchable as the web.

Based in Atlanta, GA and New York, NY, co-founder and CEO Joe Ellis is obsessed with everything machine learning, artificial intelligence, vRPA, and workflow automation—all culminating in Vidrovr.

Click here to meet the rest of our innovative portfolio companies.

Mistake: Emphasizing company potential over people potential

When I began investing over a decade ago, I evaluated deals using a holistic lens: a well-built company with an innovative product made for a good investment. Using this company-centric framework, I invested $1M into 20 companies during my first year that I thought had a good shot at success, but within 12 months, all but a few (shoutout to ExpenseCloud, Klout, Ticketmob, and Burstly—all 4 of which I later sold my shares in for $2.7M) were clearly failing. 

Frustrated, I began taking inventory of the different factors that could’ve prevented them from succeeding, but their solutions, business models, and market influence all checked out. And yet they were still failing. 

At the time, I was meeting with founders and listening to traditional pitches and predictive cash flows, which always painted a really pretty picture of the future if all went well. But over time, I understood that expecting things to go according to plan was unrealistic. The only real predictable factor with startups is that their industries will inevitably shift, and their founders will have to find ways to effectively respond. So if change is as inevitable and uncontrollable as the weather, then what aspect of each startup can we look to for constancy?

I decided that if I wanted to be an adept predictor of startup success, I would have to develop a specialized talent in evaluating the founders themselves.

Operation: Founder Expert 

I started observing and analyzing the factors that set successful founders apart from others. What psychologically differentiated them, and how did the stories they told us about themselves differ? 

The answers that I found won’t come as any surprise to literature buffs: the most successful founders had shared characteristics rooted in the defining moments of their lives. In other words, they all followed the archetypal hero’s journey. Their personal stories often hinged on a moment (or moments) when they struggled deeply but somehow found a way to persevere or overcome an obstacle they couldn’t control or foresee.

These kinds of stories gave me a glimpse into a founder’s internal GPS, which could be used to predict how they would handle the chaos of a startup’s lifecycle. I began to see that some founders are more wired for adaptability, so I stopped asking for their pitches first and started asking them to tell me about themselves—their stories, their challenges, their fears. The answers they shared in conjunction with the success or lack of success they inevitably experienced provided me with the evidence I needed to build Outlander’s Founder Framework.

Building the Framework

Our Founder Framework is the most important evaluation tool we use when deciding whether or not to invest in a startup, and like the industry we work in, it’s constantly evolving as we learn more about founders and their psychological makeup. Currently, the Framework consists of 38 characteristics divided into four categories: vision, intelligence, character, and execution. Like any good literary hero, outstanding founders need strength in each area.

Vision: Think of a founder’s vision as their map. It might not be extremely detailed, but it gives them a necessary outline for the journey that lies ahead of them. It helps them predict hurdles, and it gives them a compelling way to convince others to join in on the quest. Founders with great vision aren’t as focused on the ways they want to get to their destination; they tend to focus on the fact that they’re dedicated to getting there by any means necessary. 

Intelligence: When I refer to intelligence, I’m not talking about how high their IQ is or where they got into college, although those things don’t hurt. What I mean is that they have a great internal compass—meaning knowledge of their venture’s industry, the skills to navigate through complications, and experiential knowledge that led them to create this particular solution. When their ship goes off course (and it will), they have the intelligence to get back on course and to learn from the detour.

Character: A lot of extremely successful founders have been what people might refer to as “a real character,” but when I’m evaluating a founder’s character, I’m actually trying to find out what fuels them. I’m looking for homegrown mental fortitude, something akin to grit and determination. A lot of people say they’re ready to give all of their time and energy to see a venture through, but only a handful of them really mean it.

Execution: A founder’s ability to execute is all about their ability to make choices. Founders with this strength know how to combine their vision, intelligence, and character in order to arrive at the next course of action quickly and deliberately. They must be open to adapting their approach or perhaps even looking for opportunities to experiment. 

Founder Framework Applied

At Outlander VC, we believe in the methodology behind our Founder Framework, and we apply it early when determining whether or not we will invest in a company. So what does that look like in a practical sense?

Founders must score highly in all four categories or we will not invest no matter how good their idea is. That may sound extreme, but let me ask you:

Without a visionary founder, who will entice investors to give the startup an opportunity?

Without an intelligent leader, how will a company know what the next best move is?

Without strong character, who will keep pushing the team and find ways to renew morale?

And without someone ready to execute, how will the startup progress to new levels?

After 14+ years of investing, I know this much: even the greatest ideas are doomed to fail without a well-rounded and dynamic founder to lead the way.

Food production isn’t keeping up with the global demand, as Earth’s middle class is expected to double – with consumption levels alongside it – by 2030. The population’s demand for nutrients has outpaced production since the mid-1990s, with the most acute shortages occurring in developing economies. Drought and erratic weather conditions from global climate changes have accelerated the problem even further, with estimates that it will reduce crop yields 10-20%.

Fortunately over the last few years there’s been a surge of interest from tech entrepreneurs and venture capital firms in confronting this challenge by leveraging the latest advances in technology. In 2016, the modern farm has moved far beyond merely genetically enhanced seeds; it’s becoming a conglomeration of robots, aerial imaging, and data analysis. There is a new wave of innovation to make farms “smart,” ultimately resulting in substantially increased crop production.

As Pablo Borquez Schwarzbeck (CEO of our portfolio company ProducePay) points out however, while nearly all the attention and capital is flowing toward improving crop yields, that’s just one piece of the bigger puzzle. As yields improve and overall production increases, there remains a massive financial bottleneck holding back the industry’s ability to actually bring more of those crops to market.

Once a farm has fresh, nutrient-rich produce ready to sell, they get it to market by way of a distributor (a.k.a. a wholesaler), who takes their fresh produce and sells it to retailers like grocery stores and supermarket chains for a commission of 8-12%. It typically takes 45 days from the date a farm ships its produce to when it – and the distributor – actually gets paid, however. And farms, whose expenses are disproportionately weighted to peak harvest season, don’t have the cash flow to wait that long.

Normally, a business owner would negotiate a line of credit with a bank to handle a cash flow problem like this, but banks won’t lend to farmers. In their eyes farms are too high risk because the collateral – the farm’s produce – is perishable, hard to track, and hard to value. To enable farmers to cover short-term expenses, the distributors in the industry – whose wellbeing is tied to the farmers’ shipments – took on the role of making loans to farmers that get repaid a few weeks later once money flows back upstream.

Distributors are in the business of wholesaling produce, however; they don’t want to be banks. Their need to make loans to farms has created a bottleneck holding back their growth: they can only work with as many farms as they can afford to lend money to. So as new technology and farming practices improve yield, the financial bottleneck is only going to become more strained. Distributors can’t bring massive amounts more produce to market because they can’t afford to loan more money. (Imagine if an Uber driver had to loan every rider the money for their ride and not get paid back or earn their cut until 6 weeks later; they wouldn’t be able to offer many rides.)

We made our first agtech investment a few months ago in Pablo’s company ProducePay, which is pioneering a new model of financing to solve this problem.

He and his team are creating a proprietary tech platform that makes it easy for farms to record data on their produce shipments and for distributors to accept and record market price information according to the daily movement of the fresh produce commodities market. This valuable real-time data enables to ProducePay to responsibly provide growers payment advances the day after the produce leaves the farm — essentially significantly accelerating their cash flow without a cumbersome bank loan process.

Envision you, like Pablo’s family, run a farm in Mexico that partners with a distributor in California to sell your produce on the US market. ProducePay will vet your request then – assuming you meet their criteria as a USDA compliant business – they will set up a cash flow plan for your farm’s unique circumstances. As data comes in on the size, characteristics, and location of each shipment, the company will automatically advance the grower the agreed upon percentage (up to 80%) of that produce’s market value. On average this amounts to $25,000 advanced to the farm every day throughout the harvest season.

The distributor in California isn’t disappointed that a farm they usually lend to is getting financing without them either; it means they now have that more working capital to either invest in their own operations or lend to other farms that don’t yet use ProducePay. The distributor earns far more money by wholesaling a greater volume of produce for 10% of the sale price than they ever did making short term loans.

This win-win-win scenario is rather unique: the incumbents in this industry actually want to be “disrupted” and are ProducePay’s leading referral source for new fresh produce farming clients.

The Borquez family has been farming in Mexico since Pablo’s great-great-grandfather ran the show. His father grew their farm in Obregon from 30 acres to 3,000 acres over the last 100 years – a journey Pablo saw every facet of as a child growing up helping with the farming and operations. In particular, he recalls the lifestyle of a family business where most of the year is spent preparing for a 2-3 month harvest season in which the entire year’s income is made (and heavily subject to the luck of weather, etc.).

After college, he moved to the US to work on the finance and Grower Relations team of a large produce distributor in Los Angeles. There he realized how frustrating lending to farms like his is from the distributor’s perspective. The distributor’s inventory from farms could only grow in balance with their ability to lend, and it created massive credit risk for the company to do so.

When he started his MBA at Cornell a couple years later, he had decided he wanted to find a solution to the problem. Midway through his degree he settled on the idea for ProducePay and partnered with the development studio Coventure to build out the basic tech platform to test the concept in the field. The first advance ProducePay made – as an MVP in March 2015 – was $100,000 to help get $250,000 of asparagus to market. The test went perfectly: in just 30 days, the farm repaid the principal, plus ProducePay’s fee of 1% produce value ($2,500).

The company has since raised a $1.2M lending facility for its first season (June-July), a $6M one for its second season (September-January), and has surpassed it’s goal of enabling $100M in produce shipments within the first year of operations. The platform has already supported large shipments of asparagus, grapes, mango, and lemon coming into the US, with berries, squash, tomato, and other produce coming soon.

Although ProducePay works with US growers, early success has been focused on distributing Mexican and South American produce into the US market. In addition to being the largest developed market for agricultural products, the US offered the best publicly available data on daily produce imports (the Department of Agriculture monitors the price movements of ~100 produce commodities. That information helps the company offer financial solutions with the most accurate predictive future market price metrics around.

The US market is just the start though. Pablo has seen interest from farms and distributors globally, and the ProducePay model is a particularly powerful solution for developing countries where farmers don’t currently have access to any sophisticated financial infrastructure. Moreover, his team is working to make the ProducePay platform a dynamic marketplace where farms and distributors can more efficiently find and trade fresh produce around the world.

If they can more efficiently facilitate the movement of agricultural products in markets around the world, he thinks, the elimination of financial bottlenecks will drive an increase in the overall supply of fresh produce actually becoming available to the end-users, everyday people.

© Outlander VC. 2022.