For 14+ years, we’ve invested in unicorns like Lyft, Wish, Gusto, and Scale at the earliest stages. On April 4th, you’re invited to meet 5 of our current early-stage portfolio companies at the Outlander Spring Showcase

Here’s a sneak peek at the lineup:

Crow Industries 

🎯 autonomy, ML/AI, robotics 📍 Scottsdale, Arizona
🎙 James Crowell, CEO + Founder 📧 info@crowindustriesinc.com

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

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.


HavocAI 

🎯 maritime autonomy, USVs, attritible 📍 Providence, RI
🎙 Timothy Rhatigan, CEO + Co-founder 📧 info@havocai.com

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.

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 📧 adit@luladelivery.com

Lula Convenience builds digital commerce enablement software for convenience stores, enabling them to swiftly introduce modern websites, delivery & pickup on every viable channel (i.e., Doordash, Uber Eats, Grubhub, and more).

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).


Skyways

🎯 autonomy, AI, aerospace, drone 📍 Austin, TX
🎙 Charles Acknin, CEO + Founder 📧 charles@skyways.com 

Skyways is revolutionizing how we think about transportation by building large autonomous cargo drones to transport people and cargo.

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.


Tryby

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

Tryby AI is building hyper-realistic, advanced conversational AI for businesses that answer and execute on 100% of calls, 24/7.

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 to learn more about these game-changing startups! Meet the rest of our portfolio here.

Building a successful startup requires a founder with exceptional vision, intelligence, character, and execution to navigate the inevitable ups and downs. In the Outlander Unicorn Rodeo Series, we sat down with founders Blake Hall of ID.me, Fritz Lanman of Mindbody & ClassPass, Jonathan Neman of sweetgreen, Josh Reeves of Gusto, Matt Pohlson of Omaze, and Waleed Nasr of Medely to dig into the early strategies of these now-unicorns. 

Here’s their advice for founders beginning their startup journey:

1. Conviction is the foundation of startup success: First and foremost, only start a company if you can’t imagine not doing it. Startups require immense resilience and sacrifice that can only be justified by a founder with a greater level of conviction. The most successful founders truly understand and deeply resonate with the problem space they’re trying to solve. Compelled by how their vision will change the future for the better, impact-driven founders are more likely to persevere when things inevitably get tough.

“Don’t do it unless you have to do it—unless you’re just so compelled that it’s not a decision.” — Fritz Lanman of Mindbody & ClassPass

“Companies don’t exist for the sake of it. We exist to fix stuff. It all starts with the problem space. It all starts with something being broken and painful, and you’re so compelled to try to fix that thing that you almost have to start a company to fix it because it’s not getting fixed otherwise.” — Josh Reeves of Gusto

2. Build a complementary, mission-driven team: Identify your strengths and weaknesses as a founder, then seek mentors and team members who augment your capabilities. Beyond complementary skills, your core team must share your conviction and be bought into the vision. Invest in a strong relationship foundation with your team, especially co-founders. Company culture can make or break your long-term success, and hiring a people/HR leader early can enable founders to remain focused on product and sales without sacrificing the top-tier talent needed as the company scales.

“The single most important thing for a first-time founder is to get mentors that help you with your blind spots. Be really cognizant of the archetype that you fit into, and build a founding team that complements but doesn’t duplicate your skill set.”  — Blake Hall of ID.me

“Hiring as a search for alignment. You don’t convince someone to join, and they don’t convince you to hire them—it’s both parties figuring out, ‘Can we do something great together and having an intentional approach to that?’, whether it’s the values, motivation, skill, alignment approach, or whatever you create.” — Josh Reeves of Gusto

3. Storytelling is an early-stage founder’s most valuable tool: Your ability to sell your vision is crucial for not only fundraising but also hiring, sales, product development, and beyond. Investors invest in the story, not just the numbers—especially in the early days when experienced VCs know not to expect flashy metrics yet. Likewise, storytelling is critical in mobilizing a team around a shared vision. In the early days, there’ll be less capital to offer potential hires, so founders must sell the vision to attract top talent. The best way to craft a compelling pitch is by going out and pitching over and over, A/B testing your way through it. Similarly, get your hands dirty and personally tackle customer support and product testing challenges. This hands-on approach gives you greater insight into your company, helping you lead and fundraise more effectively.

“The most underrated skill set for an entrepreneur—the one that I would argue might be the most valuable, but people invest the least in—is storytelling. Investors use numbers to fortify the story, but they’re investing in the story.” — Matt Pohlson of Omaze

“If you can’t convince a great engineer to come and work for you and build this thing, you’re going to have a really hard time building a successful company.” — Fritz Lanman of Mindbody & ClassPass

“But for growth-stage investors, when you’re coming up to pre-IPO type level, the story matters 25%. Your numbers matter more than anything. Being to being able to tell the story about your numbers became more important than just the story.” — Waleed Nasr of Medely

4. Prioritize everything against your North Star Metric: Have a deep understanding of your metrics from the early days. Prioritize initiatives that scale your core business and contribute to your North Star Metric (NSM). Start small and remain capital-efficient in the early days by focusing on what advances your value proposition. By staying lean and agile, you can prove your business proposition without over-raising capital and, in turn, raising the bar for your next round or exit.

“Think about what that core business is and make sure you’re investing in what your real value proposition is, not some of the other stuff on the periphery.” Jonathan Neman of sweetgreen

“The military teaches that you always need to lead two levels down. For me, I’m responsible for the profits and losses (P&L). That’s ultimately what I’m accountable for to my investors and the board. So, in order for me to have confidence that my reports are bringing clarity and focus on what matters, they have to show me that they understand how the different things they do tie back to our P&L and then say, based on this, here are the KPIs that are always true.” — Blake Hall of ID.me

Throughout the Outlander Unicorn Rodeo Series, every founder emphasized the importance of vision, resilience, effective team-building, and alignment with the company’s mission as the cornerstones of successful early-stage startups. Without this foundation, it’s easy for founders to lose the forest for the trees. Unsurprisingly, each founder emphasized the need for a North Star Metric to serve as a compass for all aspects of company building. 

However, as Fritz Lanman advised, there’s no substitute for a founder getting their hands dirty, which is why hearing fellow founders’ experiences is often more enlightening than generalized advice. So, we invite you to watch the full firesides with Blake Hall of ID.me, Fritz Lanman of Mindbody and ClassPass, Jonathan Neman of sweetgreen, Josh Reeves of Gusto, Matt Pohlson of Omaze, and Waleed Nasr of Medely to soak up all of their expertise, and save your spot for our upcoming events, too!

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, Twitch.tv, 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

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:

BoxedUp 

🎯 SaaS, B2B, rental, e-commerce 📍 Atlanta, GA
🎙 Donald Boone, Co-founder & CEO 📧 hello@tryboxedup.com

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.


Heartbeat 

🎯 SaaS, paid membership, virtual community 📍 Atlanta, GA
🎙 Murtaza Mambot, Co-founder & CEO 📧 founders@heartbeat.chat

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.


Huddle 

🎯 future of work, marketplace 📍 Miami, FL
🎙 Michael Saloio, Co-founder & CEO 📧 mike@huddle.works

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 📧 founders@straptvending.com

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.


Vidrovr 

🎯 AI, ML, computer vision, enterprise software 📍 New York City, NY
🎙 Joe Ellis, Co-founder & CEO 📧  joe.ellis@vidrovr.com

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.

While a great deck and pitch are imperative, they’re just the tip of the fundraising iceberg—especially in today’s market, where investors do more diligence before writing a check. Since securing a “yes” from investors from an excellent first pitch is unlikely, founders need a 360° fundraising strategy to convert pitches into capital. So, after securing a first meeting and nailing your pitch, here’s how we coach our portfolio founders through the two critical “closers” of a successful fundraising strategy: consistent follow-ups and a robust data room at the ready. 

Follow up, follow up, follow up

Fundraising is a time-consuming necessity for founders, so being prepped and ready is paramount. Immediately after a pitch, have your first follow-up email queued to send, thanking them for their time and providing access to your data room. Quick responses throughout the fundraising process signal that you are serious about your raise, proactive about potential concerns, and respectful of their time.

At every stage of the raise, your follow-ups should be consistent and professional, acting as an extension of your pitch. Here’s how to wield follow-ups to maximize fundraising efforts:

  1. Address concerns directly and quickly. Typically, what separates founders from a “yes” is how quickly they alleviate their potential investor’s concerns. If they voice concerns during the initial pitch, use your first follow-up email to address them directly. Don’t mistake an investor’s concerns for an outright rejection. Instead, take it as an invitation to address their concerns head-on.
  2. Clarify where you stand. The fundraising advice we always give to founders is, “The second best thing to a ‘yes’ is a quick ‘no.’” So, in your follow-up emails, ask for updates on your status in their pipeline, including the expected timeline and next steps. Equipped with this information, you can better tailor your approach to each investor’s investment process and prioritize your time accordingly.
  3. Build excitement between rounds. The reality for startup founders is that you are always either actively or imminently raising. So, it’s wise to provide strategic updates to your current and potential investors to prime them for your next raise. Create excitement between rounds by providing quarterly updates on your progress, celebrating important milestones and new hires, and boosting any prominent media features. Then, tap this primed audience to announce an upcoming round and share the exciting milestones, such as securing notable investors and closing the round.

Build a robust data room in advance

Every investor operates from a unique investment thesis, which prioritizes different elements of your business accordingly. A robust data room is the most efficient way to quell as many investor concerns as quickly as possible, freeing you up to make more intros, book more meetings, and nail more pitches. Failing to prepare these materials in advance will delay your response to investor concerns, potentially jeopardizing funding.

Your data room has to be secure and accessible by only designated people, such as your potential investors. An impressive data room will show investors that you’ve put time, energy, and thought into how you’re running your business today and how you plan to run your business in the future, including but not limited to:

  1. Pitch Deck: Include a copy of the deck from your initial meeting for investors to review.
  2. Business Plan/Operational Model: A detailed description of the company’s strategy, target markets, competition, monetization model, and projections for the next 3-5 years.
  3. Financial Information: Historical financial statements (Profit & Loss, Balance Sheet, Cash Flow), financial projections, capitalization table (the more information the better, including ownership percentages, shares, options, and warrants), and a list of all investors and terms from previous raises.
  4. Legal and Compliance: Formation documents (Articles of Incorporation, Bylaws, etc.), voting agreements, first refusal and co-sale agreements, stock purchase, shareholder agreements, and any outstanding or potential legal issues.
  5. Governance and Corporate Structure: Information about board members, board meeting minutes, and details on any subsidiaries or joint ventures.
  6. Term Sheet: If you don’t have an executed or theoretical term sheet to include, let potential investors know the general terms and funding mechanism of the raise.
  7. Market Research: Supporting documents from your research on your target audience, market size, competitive analysis with features and pricing, and trends.
  8. Customer Information: Key customer metrics (customer acquisition cost, lifetime value, cohort analysis, and churn rate), key customer insights (case studies, testimonials, or success stories), customer contracts and agreements, and anonymized user behavior data, if any.
  9. Sales and Marketing: A detailed overview of your marketing strategy, sales pipelines, metrics and processes, and sample materials (one-pagers, decks, fliers, etc.).
  10. Team Information: Biographies and CVs of key team members, current organizational chart, details on advisors and their roles, and future hiring plans.
  11. Technology Information: For hardware, include a spec list with pricing, vendors, and/or factories. For software, include system architecture diagrams, and details about the technology stack, such as API documentation, infrastructure, security measures, third-party integrations, and any “special sauce,” like ML or AI.
  12. Product Information: A high-level product roadmap showing past milestones and future plans, including product descriptions, specifications, tutorials, and demos.
  13. Intellectual Property: Details and copies of patents, trademarks, copyrights, and other intellectual property rights, including IP-related agreements or disputes.

An initial pitch can only cover so much and dive so deep, so providing supplemental materials shows you’re a prepared, strong operator who has done their homework on the business you’re trying to build. Think of your data room as not only a repository of your financial and operational documents but as a place to illustrate the full breadth of your vision. Include supporting documents that speak to your future vision for the business, such as future product development, future sales or marketing initiatives, and other strategies that you couldn’t cover in your initial pitch deck. 


Early-stage investments are a bet on the founding team’s long game. As you court potential investors, part of your job is to build their trust and conviction that you understand the problem you’ve set out to solve and are the right person to build its solution. So, as you implement these follow-up strategies and build your robust data room, treat each piece of outreach or supplemental materials as an extension of your pitch: professional, optimistic, and well-crafted. 

And if you’re an exceptional early-stage tech founder building something big, we want to hear. from you! Learn more about Outlander VC’s investment strategy and connect with our investors now.

The journey of startup fundraising is a process of risk removal. At each Series, certain risks are expected by investors, certain risks diminish, and the company gets more valuable as they do. With enough foresight, founders can leverage the timing of their raises and control the answer to the age-old startup question, “What are we worth?”

For our first Outlandish Speaker Series, we hosted serial founder and venture capitalist Eric Feng to tackle the importance of timing in fundraising. With a background in computer science, Eric has successfully built and sold three companies and loves investing in the consumer, media, and commerce sectors. He previously led e-commerce at Facebook, led early-stage consumer Internet investments at Kleiner Perkins, and was the founding CTO and Head of Product at Hulu. As of this Field Guide, he is the co-founder and CEO of Cymbal and a General Partner at Gold House. 

Here’s how Eric Feng advised founders to think about and time their next round of funding. 👇

  1. Startup founders wield a key advantage: controlling when their company is priced. Private startups have no publicly traded shares, so their valuations are determined during fundraising rounds. Timing is a significant factor, especially during economic uncertainty or downturns when securing funding and higher valuations is difficult. With this foresight, founders who manage their runway well can control the timing of their raises and the context of their company’s valuation, laying a sturdier foundation for future funding rounds. 
  1. Fundraising prices fluctuate with assumed risk. Now for the other half of the equation: the check writers. In exchange for their capital, investors receive equity or partial ownership in a startup, the price of which is based on the company’s valuation and assumed risks. From an investor’s perspective, the early days of your startup are when the company is least valuable: too many risks and very few assets. As such, early-stage investors invest in higher-risk companies at lower prices. As your startup grows, your risks begin to diminish, your assets grow, and the company becomes more valuable. Growth-stage investors invest in lower-risk companies at higher prices. As such, founders must continue to remove risks as they grow.
  1. In between rounds, use your runway to remove risks and grow value. At least, this is the expectation of your current and future investors! Now that you’ve raised capital, there are six general categories of startup risk you can tackle to grow your value: 
  1. At each Series, focus on minimizing stage-appropriate risks. Investors focus on different risks depending on the stage of your company. At the Seed stage, the unknowns around profitability, monetization, and market fit are normal risks, but investors want to feel bought into your vision and founding team. At Series A and B, it’s normal not to have revenue, but investors will want to see a working MVP and product-market fit. At the Series C+ stages, it’s okay not to be profitable if you demonstrate that your business model can scale to profitability.
  1. Plan for your next raise immediately after closing your current round. Don’t wait until you’re running low on cash to think about your next round. Instead, consider what investors will expect from your company the next time you raise capital and prioritize your efforts accordingly. As you map this out, keep a buffer of ~1 year of runway before your next raise to account for any unknowns and prepare for the raise. Great founders are always “fundraising,” even in between raises. In the interim, keeping current and potential investors informed as you diminish risks and grow value is an excellent way to prime them for your inevitable next raise.
  1. If you lose control of runway, you lose control of fundraising. Regardless of stage, your most important asset to manage is runway. If you burn through your runway too quickly, there are only two options: raise additional capital or shut down.  Instead, try to raise more than you need to remove risks and grow value, and always spend less than you raise. Otherwise, you may find yourself with 6 months of runway left, and you’ll be forced to raise capital whether you want to or not. And if you’re forced to raise before addressing stage-appropriate risks, investors will be less willing to take a gamble on your venture, which can impact both your potential valuation and capital raised.

Marc Andreessen says, “Running a startup is also how I think about raising money — it’s a process of peeling away layers of risk as you go.” And as you peel, always keep your next raise and its potential investors front and center. Investing your energy and runway into minimizing stage-appropriate risks allows you to control the timing and context of your startup’s price.

Join us for the next Outlandish Speaker Series to ask our guest experts all your startup Qs! Check out our Events page to learn more.

Founders are the captains of a startup, steering the ship and crew toward their vision of the future. Your relationship with fellow co-captains and the rest of your team will dramatically impact how efficiently and effectively the ship can progress. The stakes are even higher between co-founders, where soured relationships can turn into dissolved cap tables, hefty legal expenses in untangling, or even the company’s failure.

So, we asked the founders of the Outlander Community about their hard-learned lessons in failed co-founder relationships and advice for productively handling co-founder conflicts. Though all agreed conflict is inevitable, keeping the resolution process productive requires the same ingredients as any other relationship: clear expectations, proactive touchpoints, data-driven communication, and support from neutral third parties.

Step 1: Explicitly outline expectations

After messily parting ways with co-founders, many surveyed founders’ biggest regret was not catching misaligned expectations until it was too late. These founders were adamant about co-founders delineating their shared vision, values, and expectations before signing any contracts. United by more than money or clout, co-founders who rally around a shared vision, values, and expectations are less likely to implode from infighting.

For example, consider how aligned your answers are to the following questions:

Next, it’s time to codify your agreed-upon responsibilities and conflict resolution process. When conflicts arise, the legal agreements governing your startup will dictate what options are available. From your articles of incorporation to operating and shareholder agreements, these documents outline the rights and responsibilities of each co-founder, ownership stakes, decision-making processes, and dispute-resolution mechanisms. Safeguarding your legal rights and obligations in an operating co-founder agreement is a vital first step for equitable, productive conflict resolution down the line.

Step 2: Be proactive with routine co-founder touchpoints

While a shared vision can help anchor difficult conversations, it’s just as easy for such aspirations to get lost in day-to-day operations. With so much to juggle, surveyed founders recommend scheduling a routine co-founder meeting specifically to get issues out in the open regularly and addressed as quickly as possible. With frequent opportunities for direct dialogue, co-founders can address issues incrementally instead of letting them sour the working relationship.

For the co-founders of Heartbeat, establishing a standing co-founder dinner ritual has been paramount to preserving their working relationship. Every Thursday, they grab dinner and air out every annoyance, frustration, or problem that needs addressing from the past week. “Knowing we had this time each week ensured there were never any pent-up emotions,” explains Murtaza Bambot. “We got better and better at voicing problems and dealing with them together,” and ultimately, this ritual “created the best working relationship I’ve ever had with anyone.” 

A good co-founder dynamic boils down to good communication. By addressing conflicts routinely and directly, you and your co-founder can focus on building your company, not fighting.

Step 3: Use a data-driven approach to problem-solving

With your expectations outlined and routine touchpoints set, resolving conflict productively will boil what you say and how you say it. In difficult conversations, things can quickly become emotionally charged, so it helps to stay anchored in a shared value (i.e., your company’s mission) and lead with the facts. 

Using a data-driven approach to solve problems was the most frequent advice from surveyed founders, but with an important caveat: Don’t dismiss emotional responses in pursuing this approach. A co-founder’s emotional response offers valuable insights into their motivations, values, and more. Instead, name the emotions for what they are: a reaction to your interpretation of a situation. And, in the words of Michael Saloio of Huddle, “Conflicts don’t lie inside facts. Conflicts only lie inside our interpretations of those facts. It’s tough to create real solutions when the facts aren’t clear.” 

Here’s his fact vs. interpretation framework and how he taught his co founder and team to use it:

  1. Take a piece of paper and draw a line down the middle.
  2. On the left side of the paper, write down the facts about a given situation. Facts are ONLY things you can prove in reality: numbers, things someone actually said or did, etc. You’ll likely find that the facts are simple, and there aren’t that many of them. 
  3. On the right side of the paper, write your interpretation or the story you’re telling yourself. Two people rarely ever share the exact same interpretation, so this exercise opens up a discussion where people can share their experiences instead of arguing. You might also find you had a whole entangled story you thought was real, and it’s not.
  4. Create a new narrative by replacing interpretations with facts. Think of this as creating a blank slate. The goal is to move away from your individual interpretations of the situation and create a new, shared narrative so that you can move forward.
  5. Decide your next steps based on the agreed-upon facts. Suppose you acquired 50 new customers in Q1, and your target was 65. One interpretation of this situation could be: “We suck, we’re behind, I’m no good at this, it’s [insert person]’s fault, etc.” However, another interpretation could be: “Our product is showing a lot of promise, we’re so close to meeting our goal of 65, we’re moving in the right direction, etc.” After reorienting the conversation around the simple facts, the shared narrative and subsequent action plan could be: “We got 50 customers in 1Q. Our stated goal was 65. Based on what we learned, let’s reset our goals and try three new customer growth strategies.”

Other founders added that as you work to create a new narrative, focus on trying to understand your co-founder’s perspective, not winning the argument. If you hit a wall, pause and take a break from the conversation. When you reconvene, stay solution-oriented by anchoring your difficult conversations in your shared vision and values. Remind each other about what you’re striving toward. Dive back into the problem at hand.

Step 4: Bring in a third-party perspective

Often, co-founders get so deep in the weeds of a conflict that they can’t see the forest for the trees. That’s why you have mentors, executive teams, and board members: to support your business through issues like a complex co-founder conflict. So, if direct communication proves unproductive, it’s time to bring in a third party. 

For example, Renato Villanueva from Parallel suggests role-playing a difficult conversation with a neutral third party. With the unbiased person pretending to be your co-founder, practice delivering your feedback or approaching a conflict, seeing how your pretend co-founder reacts. Try a few different tactics to see which delivery avoids unnecessary escalation. Similarly, bringing a facilitator to help you and your co-founder find a mutually satisfactory resolution. Mediation can be a cost-effective and less adversarial alternative to litigation, preserving the working relationship and potentially avoiding legal battles. 

In some cases, co-founder conflicts may reach a point where an amicable resolution seems impossible. At this stage, it is crucial to consult an experienced business attorney before considering any legally binding decisions. A skilled attorney can provide valuable legal advice tailored to your specific situation, such as understanding your legal rights, obligations, and potential remedies, including co-founder exits. However, litigation can be costly, time-consuming, and may harm your startup’s reputation, so it should be your last resort to resolving conflict. 


Co-founder conflicts can be challenging and emotionally charged, threatening the very foundation of your business. Though conflict is inevitable, the Outlander Community is full of founders who have been exactly where you are now. So, learn from their mistakes and get explicit about expectations, be proactive about co-founder conflict resolution, and don’t wait until conflict impacts the business’s operations to seek third-party support and legal advice to protect your rights and find a resolution.

Outlander VC invests at the earliest stages, which means that most of our portfolio companies are pre-revenue and pre-product businesses. All of these early-stage startups follow a similar trajectory: First, founders must turn their idea into a reality by building a Minimum Viable Product (MVP). Then, it’s mission-critical to get that MVP into your potential customers’ hands to test and validate. Based on this feedback, it’s time to iterate until you’ve built a product your customers are willing to pay for, and viola: revenue! 

Effectively developing your MVP into a full-fledged product requires a lot of prioritization. Rome was not built in a day, and your solution won’t be either. After advising countless early-stage founders through this process, I’ve distilled this process into three distinct phases: designing, building, and iterating. Here are the most important considerations and most common founder pitfalls for each stage: 

Phase 1: Designing

  1. First and foremost, understand the objective of your MVP. Think of your MVP as an experiment: its purpose is to validate your hypotheses and gauge market interest. As such, your MVP should be the stripped-down version of your envisioned product, containing only the core features and functionalities required to solve a specific problem. By focusing on the essentials, you can quickly and cost-effectively test your product idea before sinking significant time and money into product development.
  2. Quantify what “success” looks like before you build. To prove your solution is viable, define clear and measurable objectives for its initial iteration. The data you collect from your MVP will validate whether your product solves a real problem for your target market. These objectives should ladder up to your North Star Metric and will serve as your initial KPIs. Keep in mind that you will use this data to demonstrate the feasibility, viability, and early traction of your product concept to attract investors or potential partners. 
  3. With MVPs, simplicity is key, and done is better than perfect. In fact, your initial product should be somewhat terrible because it was built as quickly and efficiently as possible to get it into the hands of someone to give you feedback. You do not want to spend a year or two in development only to get it in customers’ hands and realize you’ve spent a long time building the wrong product. 

Phase 2: Launching

  1. Attract initial users. After you’ve built your MVP, it’s time to get beta customers to test your product and provide feedback. Move quickly to get your MVP into the hands of potential customers. Consider offering trial versions or beta programs to attract early adopters and gather feedback. 
  2. More users = more data. Be wary of spending too much time in stealth mode. Limited beta user access testing also limits the amount of data you can collect. I often hear early-stage founders say things like, “I have ten people on a trial right now, but I have a hundred waitlisted!” Why are those hundred people not on a trial, too? More people testing your product earlier gives you better data to build faster. 

Phase 3: Iterating

  1. Data-driven development is the key to growth. Establish continuous feedback loops with your users to collect insights and validate assumptions. However, do not lose the forest for the trees, and don’t act on every request. Instead, quantify the aggregate feedback from users and compare it to your analytics and metrics around user engagement, retention, and conversion rates. Leverage these data-driven insights to determine the best ways to enhance your product. When in doubt, always prioritize new feature developments by their impact on your North Star Metric.
  2. Balance scalability and stability. User needs will evolve with your product, so you’ll need to prioritize development efforts accordingly. As your user base grows, focus on optimizing your infrastructure and ensuring your product can handle increased demand while maintaining stability and performance. 

Early-stage product development is critical for turning your vision into a successful business. But the transition from MVP to full product will not happen all at once! Instead, you will gradually evolve your MVP into a full-fledged solution based on market feedback, scalability requirements, and business goals. And by following the steps outlined above, founders can effectively validate their assumptions, gather user feedback, and iterate toward building a robust product. 

Remember, the key is to get your product into the hands of users as quickly as possible, gather feedback, and leverage data to fuel growth and, ultimately, achieve your startup’s North Star Metric.

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.

© Outlander VC. 2022.