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.

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:

Backbar 

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.

📧 founders@backbar.com


Eskuad 

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.

📧 founders@eskuad.com


Made 

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.

📧 w@mademfg.co


Talli 

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.

📧 hello@talli.me


Velvet 

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.

📧 support@velvetfs.com

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

Lucy Guo’s tech entrepreneurship began as an act of rebellion. After the confiscation of her (admittedly, black market) Pokemon card and pencil profits in second grade, she taught herself coding and marketing and took her talents online. Never one to waste time, Lucy has since cofounded two Outlander VC portfolio companies: Scale AI and Passes. In 2016, Scale AI launched to help companies train, hone, and grow artificial intelligence systems. Since leaving Scale AI, she cofounded venture capital firm Backend Capital and, most recently, launched Passes, a software startup revolutionizing the creator economy with an all-in-one suite of content monetization tools.

“[Creators] are entrepreneurs,” Guo said at this year’s Forbes Under 30 Summit on October 3 in Detroit. “Most creator salaries I’ve seen match those of tech entrepreneurs and engineers. But maybe 10% of the creators are making almost all the money, and everyone else is barely making a living. There needs to be a shift.” 

Prior to Scale AI, Lucy was a product designer at Quora and Snapchat. She studied computer science and human computer interaction at Carnegie Mellon but dropped out to pursue the Thiel Fellowship. For fun, she works on random projects (that have been used by 10M+ people around the world), skydives, works out (too much) at Barry’s Bootcamp, and rides electric longboards.

At Outlander VC, we bet on brilliant founders at the earliest stages using our Founder Framework. Outstanding founders like Lucy exhibit strength across the vision, intelligence, character, and execution categories of this framework. We grabbed time on Lucy’s busy calendar to dig into her founder journey and revisit a few reasons we’ve been bullish on her from day 1.

What initially drew you to entrepreneurship?

I’ve always been an entrepreneur at heart. When I was younger, I got suspended from kindergarten for selling everything from Pokemon cards to colored pencils at school. But when my parents started taking away those cold cash dollars, I turned to tech. I discovered PayPal and figured, “Okay, cool, this is how I can make money.” So, I taught myself how to code and started making bots and in-game items for gaming sites like RoomScape or NeoPets; then, I learned to build my own websites and make money through ads. So, My Pokemon cards and colored pencils became my virtual arcade game websites and internet marketing tools.

Then, I went to college for computer science and human-computer interactions, but I was actually going to a bunch of hackathons, where I discovered startups. Then, I received the Thiel Fellowship. So, with a few semesters left, I dropped out to start building.

Any formative experiences that equipped you for startup life? A history of entrepreneurship in your family?

No, my family is pretty risk-averse. My parents didn’t even want me to study engineering because “Women aren’t made for engineering,” so I should study to be a pharmacist instead because that’s what women are better at. All of which is funny because my mom was an electrical engineer! But she would say, “I was the only one in my class. It’s unusual for women to be good at it.” She didn’t believe I could do it because, statistically, it was less likely for women to excel in engineering or tech. 

I, on the other hand, always wanted to prove myself. So, when my parents were pissed that I dropped out of college and told me I couldn’t do a startup, I wanted to prove them wrong. I had a chip on my shoulder. When people tell me I can’t do things, I like proving them wrong.

We bet on founders who act quickly and decisively as they advance into the unknown. Can you speak to your ability to be quick and decisive? 

I’ve always been a quick decision-maker because I hate wasting time. Once I gather enough data, I act. You don’t need years of data for every decision. For example, you’ll never regret firing someone too early, but you always regret firing them too late if something’s not working.

This is also why I’ve always been a pivoter. If something’s not working, I take the original idea but change it slightly to test what gets a better product-market fit. Also, I always try to create a bare minimum MVP to ensure I don’t waste too much time in the initial engineering work without feedback from the target audience. 

What motivates you?

The desire to impact the world and people’s lives is the #1 thing that drives me. A startup can only become valuable if you’ve made a significant impact on people’s lives. You won’t reach unicorn status without improving people’s lives; a startup is one of the best ways to do it. 

In the long term, I’ve imagined impacting people’s lives directly by starting a nonprofit targeting human trafficking. But, for one thing, I don’t know how to run a nonprofit, right? On the other hand, I’m good at startups. I’m good at figuring out ideas, building teams, and executing. So I figure I’m better off making money and donating to the best nonprofits. So, by focusing on what I’m good at, I can create a really f*cking big impact on other people’s lives.

What led you to seek Outlander VC to invest in Scale AI and again for Passes?

An Uber driver mentioned how Paige Craig had coined the term “Silicon Beach” and said I should reach out to him. So, I did via Twitter!

I’ve always liked bouncing ideas off of Paige because he’s invested in so many companies that he’s knowledgeable in almost every space. He’s had his hands in a lot of different early-stage companies across a lot of different verticals. So, we’ve always kept in touch.

I like people who bet on me early and people who bet on me in general. So, when I started working on Passes, I wanted him to be part of the journey again.

Let’s talk about Passes. What is Passes trying to solve? What makes Passes’ solution different?

Yes! Passes is the best place for fans to connect with their favorite creators.

One of our differentiators is that even though Passes is a Web3 platform, we built it very Web2.5 because we want to be one of the first companies to onboard people onto Web3 easily. We’re one of the new products with good UX where all you have to do is sign up with an email, pay with your credit card, etc., and then the NFT mints into a wallet we create for you.

Passes allow creators to scale one-to-one intimate relationships. I can’t go into our secrets, but most creators make money through pay-to-view and customer-requested content (think: Cameo). Passes lets them take a piece of content and DM it directly to their target audience. So, for example, if I have a segment of CosPlay fans within my audience, Passes lets me send CosPlay-specific content directly to them as a locked, pay-to-view direct message. Direct messages gave a much higher purchase rate than platforms like Patreon, where all the content is available on one feed. 

One of our creators was making $515/month on Patreon; on Passes, she is now making $40,000/month. Another creator was making $2.8k/month through Instagram subscriptions, and within 48 hours of using Passes, she’s already made $6,000. So, our tool is helping creators make life-changing money that scales with their fanbase.

Learn more about Passes here.

What are your short and long-term goals for Passes? 

My short-term goal is to make all our competitors obsolete, and Passes already has more features and is built to be more scalable than most competitors.

Creators are the future. Every creator’s becoming an entrepreneur right now. We are seeing creators starting VC funds, brands, etc., and they’re realizing the value of being an entrepreneur instead of just relying on brand deals, especially with the influence they have over their fans. So, in the long term, Passes is building a suite of tools to help creators become entrepreneurs and build wealth, too. Think about Google’s suite of tools, right? We want to be that suite of tools for creators.

You are pretty active on Twitter (@lucy_guo). As a founder, how do you use it for your business goals? 

Twitter is a great sales funnel. Generally, I am controversial because I know that’s what gets views and engagement. I think it’s better to be a little polarizing because, especially for hiring/recruiting for an early-stage startup, you can’t compete with the budgets of larger companies. The best engineers are getting paid $500,000 a year in cash. You can’t do that as a startup. People are going to work for you because they want to work for you, right? If you have super fans who are die-hard for you, they will take a huge pay cut to work for you because they believe in you. So, I think it’s much better to be polarizing in that sense. Elon Musk is an excellent example of this, actually. Even while Twitter is like paying pretty poorly, people are at Twitter because they just want to be next to Elon Musk.

Explore all of Outlander VC’s brilliant portfolio companies!

Remote-first startups have quickly become the ecosystem’s new normal. In A16z’s recent survey, 86% of early and late-stage founders said they’re opting for remote/hybrid teams, excited by the potential of a global talent pool and the added flexibility of working from anywhere. With input from some startup veterans and remote work experts, here’s what every founder needs to know to build a happy, high-performing virtual team.

Screen talent for remote-friendly skill sets. Remote work widens your talent pool to anyone, anywhere. However, your team’s happiness and performance rely on your ability to hire talent equipped to excel in a remote environment. Outside of job-related skills, experts suggest hiring talent with above-average communication and organizational skills, tech-savviness, and a self-starter mentality for the best remote team. Posting openings on remote-specific sites like FlexJobs, Remote.co, and Remote OK will also help you attract virtual-ready workers.

Be realistic about time differences. Leading a virtual team includes building trust and camaraderie between people in different time zones. Even though you can hire from anywhere in the world, time zones can get complicated fast. Keeping your team within ~6 time zones makes attending meetings, collaborating, and connecting with their teammates easier on remote-first teams.

Take onboarding seriously. Onboarding is much more than ensuring your new employee has all the necessary equipment to fulfill their role. To set new hires up for success on a virtual team, be sure to include the following in your onboarding process:

To keep your team engaged, create opportunities for impromptu connection. One of the biggest issues with remote-first teams is that it makes informal interactions more complex, resulting in increased social and professional isolation. To keep your team’s morale, collaboration, and creativity high, create virtual alternatives for impromptu, unstructured break room chats. These opportunities to connect can be as simple as adding buffer time to meetings for non-work conversation, adding apps like Donut to your Slack channel, or hosting regular coworking Zoom sessions.

Prioritize working “out loud.” An easy way to avoid siloed workers is to prioritize regular, company-wide updates from every team. To protect everyone’s time, make these updates brief and high-level. Experts suggest weekly highs/lows or holding daily check-ins covering topics like: What did you work on yesterday? What are you working on today? What is blocking your progress? Celebrating small and big wins in a group thread is another great way to keep motivation high!

From recruiting new talent to retaining longtime employees, virtual team management requires a focused and intentional approach to building culture and clear communication. With the right leadership, your remote-first team culture will translate into increased employee engagement and better organizational outcomes. Remember, remote work doesn’t mean working alone—connection matters even more in a virtual environment. 

When challenges arise for early-stage startups, VCs often advise founders to hire or build their way out of trouble. But with limited funds, people and time, early-stage founders must be strategic in their problem-solving. So, while the weight of your neverending to-do list may make hiring and building seem appealing, we recommend reaching for a quicker, more efficient tool first: optimize, optimize, optimize!

Like a good Swiss army knife, optimizing should be every founder’s go-to tool. By optimizing what’s on hand first, founders can quickly cut deadweight and adapt to changing conditions on the go without wasting time or capital. Instead, try the 5 following optimizations before sinking time and money into more intensive solutions. 

  1. Prioritize everything by impact. Before you add any new variables to the equation, take stock of your teams’ current goals, projects, and to-do list items. Rank all of your startup operations by how much they affect your North Star Metric’s growth rate. Once ranked, kill or delay low-impact projects to ensure every team member is working on an essential element of your startup’s growth.
  2. Assess team performance. Similarly, take stock of each team member. Is everyone carrying their weight and contributing to the growth of your NSM? We often find founders keep underperforming team members around for too long in the hopes that they’ll reach productivity and avoid a firing. But, as the founder, assembling an effective team is mission-critical to building a successful business and, ultimately, your responsibility.
  3. Get all hands on deck. In the early days, the entire team should be working toward your NSM whenever and wherever possible. Avoid any siloed team members by soliciting input from everyone while problem-solving and assessing team members for additional capabilities. For instance, your engineers may have insights on which features to spotlight in marketing campaigns, and your sales team may have insights on how to best streamline customer service. With everyone tackling problems together, you can quickly troubleshoot and resolve issues as they arise.
  4. Look for low-hanging fruit. To avoid overextending your team and limited resources, always ask yourself, “What’s the lowest-effort solution with the highest impact that will keep us on track?” Making a habit of looking for the low-hanging fruit first will force your team to get creative and avoid overcomplicated solutions that waste time and resources.
  5. Hack it with free or low-cost tools. The more free or low-cost tools your team can hack together, the better—especially in the early days! Before splurging on a new tool with all the bells and whistles, assess which features actually contribute to your NSM versus the nice-to-have features. Then, research low-cost or free alternatives for those must-have features to get the job done while keeping cash burn low.

Now, this is not to say that adding new team members is a bad move—it’s just not a quick one. Plus, after the months you spend on recruitment, interviews, and onboarding, there is no guarantee that your newest team member(s) will be the silver bullet you’d hoped for. Similarly, building new-and-improved versions of your solution will eventually be vital to scaling your company, but it’s all about timing. It’s a resource-intensive process that will quickly burn the finite funding and resources currently at your disposal. When it comes to choosing the right moment, be sure you feel confident that it’s feeding your NSM directly.

So, before you jump to hiring or building, reach for your optimization Swiss army knife. Founders who make a habit of optimizing what’s on hand first will stay agile and preserve resources to outlast the competition.

© Outlander VC. 2022.