Wisdom from Venture Visionary Mercedes Bent of Lightspeed Venture Partners

Welcome to Venture Visionaries, a brand-new series brought to you by Outlander VC. Hosted by Paige Craig, Managing Partner at Outlander VC, 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. 

This month, we had the pleasure of talking with Mercedes Bent, Partner at Lightspeed Venture Partners! Bent is not only an incredible investor, but a 2X founder and managing team member who has helped startups grow from the inside from $2M to over $100M in revenue. Since her early days sitting at the dinner table brainstorming fun hypothetical inventions with her father, she has lived and breathed innovation. 

Bent invests in consumer, FinTech, EdTech, LATAM, & multicultural regions and founders including Flink, Outschool, Stori, and more. In 2016, she was named a “40 Under 40 for Tech Diversity in Silicon Valley” and in 2021, WSJ named her one of 9 “Women to Watch in VC“. She has an MBA and a Masters in Education from Stanford University and an AB from Harvard University. She is an African-American of Bermudian, Grenadian, and Colombian heritage and in her free time she enjoys playing board games & off-roading in her Jeep.

Below, we’re going to unpack one of the key traits that Bent looks for in winning founders – a trait that can be crucial in the rollercoaster ride of entrepreneurship in order to build a successful business. Beyond what we uncover here, there were so many more gems in our conversation that it’s worth watching the full replay. The 1-hour chat flew by and holds incredible insights & tricks for founders and investors alike. 

Let’s dive in!

Mercedes Bent’s Top Key Trait for Founders: Learning Velocity

As Bent points out, the only constant in startups is change and “you have to be able to scale yourself faster” than your startup to grow. 

“The best founders in the world are thinking that every meeting, every opportunity that they interact with someone is a chance to learn,” Bent told us. Founders with this approach can accelerate learning cycles to quickly scaffold up their learning level. When repeated over and over again, this learning compounds and can dynamically help founders keep up with the scale of their businesses. 

For best practices in steepening a founder’s learning velocity, Bent walked viewers through a great educational framework:

  1. Consume – ingest as much information as possible
  2. Analyze – think critically about what you’ve learned
  3. Create – build or do something with this new knowledge
  4. Teach – the highest form of learning is teaching others

In the real world, this could look something like:

  1. Consume – Reading articles on an interesting topic or idea
  2. Analyze – Reaching out to specific experts and forming of opinions
  3. Create – Building, tinkering, testing, getting feedback
  4. Teach – Writing informative blog posts, joining as a guest on podcasts

For Bent, learning velocity isn’t just a checkbox either – it’s a mental metric that she actually tracks when speaking with founders from conversation to conversation. To illustrate an example, she highlighted Pamela Valdes – the first Teal Fellow from Mexico and founder of Beek.io

When AI was having a resurgence in 2022, Valdes approached Bent saying, “okay, here’s how we’re going to incorporate AI into our product” and literally “a week later, she had hit up all of the top experts at OpenAI and Anthropic and showed me an actual prototype that she had built with a new feature and the product.”

A fast-learning, action-oriented founder can simply go so much further in a shorter period of time. And often, fear of failure holds a founder back significantly more than if they could simply fail quickly, learn, and iterate. 

So how can founders develop a stronger learning mindset? 

  1. Cultivate curiosity – founders tend to be naturally curious, but a good indicator of a curious mind is when a founder “can go on and on and on about [a random topic like] roses or about kiteboarding or beekeeping” says Bent. To cultivate this more deeply, Bent encourages founders to go down the rabbit hole more and treat any conversation with anyone as a learning opportunity. 
  2. Embrace vulnerability – Bent specifically highlighted the perceived trade-off that founders often feel between confidence and vulnerability. That mindset of “I have to go in there and sell my investors, sell my future teammates, sell the product. And I have to show confidence, I can’t show any vulnerability.” But, as Bent pointed out, this fear of showing any perceived gaps and cracks can actually inhibit learning. So when a customer or an investor asks a question that a founder may not have an answer to, she encourages them not to “bluff your way through,” but rather to candidly admit “I’m not exactly sure. This is how I would think about it. How would you think about it?”
  3. Practice Advocacy – the greatest founders are often also true advocates for their customers, ensuring that their voices are heard and their needs are met throughout the product development process. “Do they understand what that customer does when they wake up in the morning, what their fears and hopes are like, what their motivations are?” Bent asks. This means actually talking to customers and really getting inside their heads.

When a strong learning mindset is present, it can touch everything and everyone in a business. A genuine obsession with learning is infectious and can translate in pitches and conversations to help founders pass what Bent calls the “time test” (how long since she checked the time during a pitch). When we, as humans, feel like we are engaging in an exciting educational exchange, we lean in, ask questions, and can’t wait until the next conversation. 

There are so many other incredible insights from our conversation with Lightspeed’s Mercedes Bent, including diving into other key founder & investor traits. Be sure to check out the full replay and sign up for our next livestream event, an interview between Outlander VC’s Leura Craig and Tim Young, the co-founder & general partner at Eniac Ventures

You can RSVP for the 6/25 live interview now!

Welcome back to Venture Visionaries, a 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.

This month, we had the pleasure of sitting down with CRV’s Saar Gur, who has invested in household-name companies like DoorDash, Ring, Patreon, and AirTable. Below, you’ll find three of our favorite takeaways from that conversation, but you can also watch the full interview here. Let’s dive in!

Takeaway 1: Dare to be weird (but with utility)

One of the standout messages from our conversation with CRV’s Saar Gur was that when he invested in Patreon, DoorDash, and Ring, for example, they weren’t obvious. In Gur’s own words, they were actually, “pretty funky” at the time.

But Gur has found a lot of investment success in looking towards the weird and wonderful, to the less obvious solutions that have early utility and could therefore make a convincing case of mainstream viability. In some cases, Gur argues that “the weirder the better,” because these differentiating qualities capture attention. It can also help founders make a stronger case for why their solution is going to come out on top. “Doing AI for customer support makes a ton of sense [but] it’s not totally clear to me why a startup is gonna win that.” So when founders can be bold enough for their solution to be different, not obvious, and then demonstrate that it’s not just a dream, but that there are early signs of product-market fit – that’s where the magic happens.

As a complete, non-tech, real-world example, Gur talked about how teaching yoga on Stanford’s campus was illegal 20 years ago and now there are more yoga studios in Palo Alto than traditional gyms. What used to be a “weird,” fermented drink called kombucha 15 years ago is now sold at Seven Elevens. Now compare this with Ring – founder Jamie Simiofff was famously rejected on Shark Tank in 2013, but his “weird” DoorBot eventually transformed home and community security, selling to Amazon for a monumental deal in 2018.

The big takeaway: dare to be weird, but also be useful.

Takeaway 2: Chase Big Markets with Bigger Conviction

To really catch Gur’s eye, he has to believe that the market opportunity is massive. “A lot of passing happens where I just can’t see how this can be a huge business […] we’re looking for businesses that can generate billions of dollars in revenue.” He loves commercially-oriented founders who are deeply in touch with the problems they are solving, are so obsessed that they will teach him something new (that’s his favorite part of the job!), and can see market opportunities from new angles. These traits are part of what make up a north star in Gur’s investing decisions: the founder-market fit.

With DoorDash CEO, Tony Xu, the founder-market fit was clear to Gur right from the first meeting, which enabled DoorDash to stand out from the other food delivery companies that Gur was doing diligence on at the time. The profoundly emotional experience with the problem had already been clear to Gur: as a parent, “at that time, you couldn’t reliably order food […] if you had young kids, they were going to melt down if that food showed up half an hour, an hour late.” But Xu’s conviction and approach made it clear that DoorDash realized they were running a logistics business and that their solution came from a deep understanding of the restaurants’ problems as much as the consumer. That combination of a deep understanding of those problems combined with the unit economic orientation and Xu’s passion & conviction sold Gur: ”I was like, Oh my God, [this is what] I’ve been looking for.”

The big takeaway: Go after a multi-billion-dollar problem and spend time understanding why you, as a founder, are the right person to lead the charge in solving it. Be obsessed and be honest with yourself so that you can develop the clear conviction needed to stand apart.

Takeaway 3: Lead with honesty, especially in tough times

Founders still have to do all of the difficult work in finding product-market fit, acquiring customers, and wearing all of the hats that come with entrepreneurship, but now with the added challenge that getting capital over the last two years has gotten increasingly harder. There will always be plenty of investors looking for great founders with even greater ideas, but the new fundraising environment is certainly more difficult.

Newer companies will find it easier to raise; Gur pointed out that “most of the companies that we invest in [are] in the first 18-to-36 months from incorporation.” Even so, Gur believes all founders of all stages will need total conviction in the problem, market, and their differentiated story to succeed. Fundraising challenges, after all, don’t stop after getting seed funding. “Even if you get it at seed, at the next stage, at Series A, at Series B – the fall-off rates are very high.” While they haven’t participated as much, Gur has also seen the industry’s rising number of down and inside rounds and shared some practical advice for founders who may be facing that exact predicament:

The big takeaway: Conviction and honesty are key. In this fundraising market, Gur sees founders who are struggling and need to raise a down round having more success in doing the hard and honest work with their current investors first before approaching new investors.

More to uncover with CRV’s Saar Gur:

We covered so much more in our conversation with CRV’s Saar Gur that is absolutely worth a listen. From how AI is a powerful accelerant to creativity to how CRV sees its role in providing value and guidance to its portfolio companies to how Facebook changed private markets forever…you don’t want to miss out on all of the other gems this and future conversations provide! Click here to watch the full interview and, if you haven’t already, join our mailing list so we can continue bringing you valuable content to help in your founder journey!

What’s coming next?

Up next, we will be sitting down with Mercedes Bent of Lightspeed Venture Partners, a renowned venture capitalist known for her keen eye in identifying breakthrough startups and top-performing founders. We’ll dive deep into the key characteristics that make founders successful and the traits that set breakthrough startups apart from the rest. You can RSVP for the 5/22 live interview or signup to receive the asynchronous viewing link afterwards here!

Event flyer featuring Mercedes Bent of Lightspeed Venture Partners

Recruiting and retaining talent is critical for scaling your startup.

As your business grows, hiring a team to turn your vision into reality creates an inevitable founder dilemma: how do you find top-tier candidates and inspire them to join you? How can you effectively screen for rockstar candidates at scale? And once you’ve assembled your dream team, how do you keep them inspired by your vision long-term?

Luckily, we hosted former SVP of Ziprecruiter and people expert Kevin Gaither for an Outlandish Speaker Series, where he shared his tried-and-true recruitment best practices and lessons from his mistakes along the way.

Recruitment Dos + Don’ts

From his time at multiple early-stage companies to growing Ziprecruiters’ sales team from 1-500+ employees, Kevin likens recruitment to dating. So, regardless of your recruitment method, keep “swiping right” until you find a candidate who excites you, avoid trying to force a fit, and beware of settling because you’re tired of looking!

Here are a few key aspects to always consider when evaluating potential matches:

✅ Define what great means. 

Before you start swiping, understand what a “great” fit for this position means in quantifiable ways. First, think of your ideal candidate, then make a list of the specific characteristics, experiences, skills, etc., that will help them succeed in the role

✅ Create benchmarks and systems for evaluating employees. 

Now that you’ve outlined your ideal candidate, it’s time to date! While interviewing, evaluate your potential hires against your ideal candidate. Using your ideal candidate as a rubric will enable you to screen and rank potential hires efficiently and effectively at scale.

🛑 Try cloning a top performer. 

When looking to expand a team, searching for a clone of already existing team members is a mistake. Using a real person as your screening rubric often leads to dead ends and potentially overlooking even better talent from a different background. Instead, reflect on what characteristics, experiences, skills, etc., enabled your top performers to succeed in their roles, then evaluate which potential hires share those qualities. 

🛑 Force yourself into liking a candidate. 

If recruitment is like dating, hiring is like marriage. In both arenas, Kevin’s advice is the same: don’t take the plunge unless it’s love! In HR-compliant terms, don’t settle for a candidate that doesn’t excite you. If a potential hire requires extensive internal convincing, they probably are not the best fit for the job.

Retention Dos + Don’ts 

After finding a rockstar candidate, it’s time to put a ring on it! The hiring process is arduous and time-consuming, so retaining your dream team is a top priority.

From the day they enter the office to their promotion to high-level management, it’s essential to create the best possible environment for employees to keep them inspired long term.

✅ Prioritize onboarding.

From the first day on the job, employees should have explicit schedules with proper training in all aspects of the business with clear delineations of how their role fits into the puzzle. New employees are not set up to succeed without adequate onboarding, which will inevitably upset the balance of their teammates, too. After the strategic decision to hire a top-tier candidate, avoid the tactical mistake of poor onboarding at all costs.

✅ Set clear expectations. 

In order to both motivate and provide security for employees, it is essential to have clear expectations on goals, firing thresholds, and company culture norms. Likewise, employees expect their performance to be reflected in promotions and pay raises. So, setting clear, quantifiable benchmarks—via sales numbers or other measurable metrics—allows them to run towards concrete goals from day one. 

🛑 Prioritize results > culture. 

Prioritizing performance alone sends the implicit message that it’s every person for themselves—quickly killing team-wide collaboration and individual motivation. Success at the expense of company culture is a sure-fire way to lose rockstar employees to companies led by more empathetic leaders who value their high-performing employees as human beings, too.

🛑 Jump straight to firing employees. 

While it’s sometimes inevitable, firing talent should be a last resort. Get curious about why your rockstar candidate is falling short. If they looked so good on paper, what is getting in the way of their success under your leadership? In the interim, finding different roles for struggling employees should be the goal of managers.

Organize for culture

The team you hire will directly impact your startup’s capacity to adapt and grow, so being thoughtful from recruitment through retention should be a high priority for founding teams. And as your company grows, you must build recruitment, hiring, onboarding, and employee retention processes that can scale with your organization and set each team member up to succeed in executing your vision.

The tools Kevin Gaither amassed through years of experience provide a vetted framework. Still, the specifics on how you execute these Dos and Don’ts will vary based on your company’s specific context and experiences—just like dating!

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

The pandemic changed how we do business, pushing sales teams to adapt to new, more virtual-than-ever strategies for reaching customers. Before the pandemic, many companies nurtured leads in person through dinners, meetings, events, etc. Now, the #1 sales and marketing asset for your business is its website because, in a virtual-first world, your company’s website is your new storefront.

Challenges of a Virtual Storefront

First, invest in your website early to set your sales team up for success. Aside from curbside appeal, your website must reflect your vision via engaging content that is easy to navigate and drives users to connect with you further. 

However, a beautiful website alone won’t do the trick anymore. 

Website conversions are down from 10% in 2010 to <1% in 2022. The pandemic expedited the shift to virtual-first shopping, which has impacted consumer activity, too. First, users are less willing to give up their personal information. Second, converting virtual leads poses unique challenges: 

Response time is critical, but so is replicating the personal touch of traditional sales strategies. As with in-person sales strategies, you need to understand: Which user in the market to buy? How do we engage with each user in a personalized way? How do we meet users with buyer intent at the exact moment they want to talk to you? 

The challenges of your virtual storefront will require tools for tracking prospects on and off your website.

Optimizing a Virtual Storefront

You will drive potential customers to your website through a variety of marketing and sales campaigns, including paid ads, outbound sequences, SEO, review sites, social media, event promotions, and email marketing. Using UTM tracking tools, Google Analytics, or a pipeline generation tool like Qualified, you can track the highest-performing sources of inbound traffic and personalize subsequent marketing touchpoints to a greater degree. 

For example, here’s how Qualified customers increase the >1% web conversion rate to +25% through their pipeline cloud:

  1. Step 1 [>1% → 10%]: Once users land on your website, engage with them directly via chat, video, or audio. Personalized, synchronous communication methods increase the >1% conversion rate up to 10%. 
  2. Step 2 [10% → 15%]: Then, with the information gleaned from the conversation, marketers can personalize outbound advertising even further, bringing the conversion rate up to 15%. 
  3. Step 3 [15% → 25%]: When your sales team reaches back out, their outbound messaging will reinforce the groundwork laid in steps 1 and 2, bringing conversions up to 25%. 

Tracking user behaviors throughout your sales funnel will enable you to identify and assess bottlenecks or leaks hindering your conversion rates, such as willingness to pay, competitive price points, when users ghost reps, time from the first touchpoint to closed-won, customer sources, and more. Then, the next step in your sales playbook is segmenting your accounts, pricing, and packaging to create a repeatable, competitive funnel.

Outlandish Sales 101 x Eric Sikola

A strong sales strategy sets the foundation for every successful sales organization. Ideally, it should focus the team around a set of shared goals, enable the team to build trusted relationships with customers, and ultimately drive more pipeline and revenue. Nobody knows this better than Eric Sikola, President and Chief Operating Officer of Qualified

With 20+ years of enterprise software and SaaS experience, Eric knows what works. Watch the replay of his Outlandish Sales 101 session for his tried-and-true selling strategies and best practices for startups so you can convert more leads than ever before.

This Field Guide is a synopsis of the first half of Eric Sikola’s 45-minute Outlandish Sales 101 presentation. Click here to view the entire presentation and audience Q&A, and access the deck!

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

The consumer packaged goods (CPG) market is massive, expanding, and becoming more and more distributed—with new players stepping into the ring every day. The $2 trillion industry encompasses the food, beverage, household, and personal care products consumers rely on habitually, making brand loyalty the cornerstone of successful CPG brands. 

Brand loyalty vs. digital marketplaces

Accelerated by the pandemic, consumer preferences have evolved along with the shift to digital marketplaces. They want the convenience and speed of online retail, but, due to the abundance of digital retailers, they are now facing a critical choice overload. With more CPG brands fighting over digital ad space and, subsequently, consumers’ attention online, the digital fatigue is real.

While online shopping is incredibly convenient, consumers will rarely convert to new products without trying them first. Think of your go-to brand of toothpaste, deodorant, tampon, etc. To convince you to switch from your tried-and-true household staple, CPG brands are bidding against each other for your attention via digital marketing campaigns with dismal conversion rates.  

In today’s world, digital just isn’t enough. CPG brands need more effective ways to convert customers, and that’s exactly what we offer at Strapt Vending.

Strapt’s win-win-win solution for CPG brands

After a frustrating encounter with a crusty old tampon dispenser, I realized that the existing vending solution—unchanged since the 70s—was past due for an overhaul. I quickly learned that solving the unmet consumer need for basic access to [paid] period products required a more symbiotic partnership between consumers, consumer brands, and hosting facilities. Otherwise, there was little incentive to bring these dispensers into the 21st century. 

So, I shifted the Strapt strategy to solve for facility and CPG brand pain points, too. In these brands’ increasingly crowded market, the problem is twofold: 1) reaching new consumers and 2) overriding their crippling overchoice dilemma. 

 Through contactless IoT dispensers, Strapt Vending offers a new and frictionless way for users to sample personal products and the first fully transparent opportunity for brands to reach customers at their exact point of need. 

Sampling <> data-driven marketing technology

For Strapt’s brand partners, this means reaching their target market at a critical inflection point: exactly when and where they need the products via a channel that brands have never been able to utilize until now.

Through high-volume sampling campaigns, Strapt offers an invaluable asset to partner brands: full transparency into user interaction data, which has historically been unavailable via old-school sampling methods.  In the words of one of our investors, Leura Craig of Outlander VC, “By taking a pretty old-school thing like vending and completely turning it on its head, Strapt is the first IRL sampling-based marketing tool of its kind. Not only is sampling an effective way to get in front of new consumers, but it’s likely a brands’ only chance at converting them away from a brand they depend on habitually. Strapt’s strategy is the future of this marketing technology, especially for CPG brands.” 

The new Strapt ecosystem

Strapt has built the ecosystem for these dispensers to thrive in a way where everyone—the brands, facilities, and consumers—can win. 

Since launching in August 2021, Strapt has partnered with three consumer brands, and our 150+ waitlist keeps growing! Via our 24 live dispensers, Strapt partners have reached 100,000+ consumers total and 4,000+ vended products—90% coming from unique users. 

Backed by Outlander VC, Strapt is raising $2M to grow our team, expand our analytics platform, and scale production to support dispenser demand. 

For expert advice on building and scaling your startup, check out our event library and Field Notes.

When it comes to choosing a co-founder, I’ve learned there’s no hard and fast path to success. In fact, I think most entrepreneurs would agree that finding and choosing an excellent co-founder is more of an art than a science. That being said, below are some tried and true ways to set yourself up for success.

Hang around the hoop

Before we even begin discussing what to look for in a co-founder, we have to talk about how you find potential candidates in the first place. My best advice to entrepreneurs has always been to hang around the hoop. For those of you who aren’t basketball-fluent, the phrase means that to have any success, you’ve got to put yourself in the best position to score—around the hoop. Your hoop is anywhere good talent might be found: meetups, conferences, pitch competitions, Slack channels . . . you get the idea. Colleges are also great resources; you can reach out to computer science professors and leaders of student entrepreneurial and innovation clubs. If you have a good idea, can tell a story, and talk to enough people, the odds of finding folks who might be interested in joining your venture are in your favor.

Look for complementary skills

This may seem like a no-brainer, but people frequently get it wrong. Many founders are drawn to people with professional backgrounds similar to their own because they already speak the same language or because they’re often in the same spaces. While it’s certainly important to gel with your co-founder, it’ll benefit you a lot more, down the line, to have someone whose strengths differ from your own.

The most common example of this is the classic nontechnical–technical co-founder pairing. The combination has many upsides because it lets the two individuals focus the bulk of their attention on different aspects of their start-up’s growth and success. But let’s say you already have a solid CTO and aren’t necessarily looking for a technical co-founder—what then? Find someone with complementary soft skills. If you’re not a stellar presenter, choose someone who can wow a room of investors. If you’ve mostly worked in silo-style roles across your career, seek out someone with team-leading experience. It’s more than OK to duplicate a similarity here and there (after all, you want to have some common ground to fall back on), but being aware of your own weaknesses and finding a way to address them with your choice of a co-founder is wise.

Get input from leaders you trust

Let’s say you’ve got a few people in mind as potential co-founders but you’re not sure how to evaluate them for fit. A few years ago, I was in exactly that position. I felt like I was on a hamster wheel and desperately trying to get off. I realized that determining whether a candidate was a good fit was much harder than I had expected. At the time, I was subleasing office space from an EO Atlanta member. He’d been an entrepreneur for almost two decades. I regularly talked with him about things I was trying to figure out, and those informal conversations were invaluable. When I told him about my problem, he made an amazing offer: “How about I interview one of your candidates and you sit in? I can show you better than I can tell you.” I happily agreed. I was able to watch him in action, and I learned a ton—especially about how to figure out when someone isn’t the right fit.If you and your potential candidates are having conversations or doing things together to get to know one another, consider inviting someone to join you—perhaps an experienced entrepreneur. If you’ve raised capital from credible investors, consider getting their input, too. Whomever you ask to join you, make sure they have a track record of evaluating talent or some experience with entrepreneurial partnerships. Your goal is to have them compensate for your blind spots.

These three recommendations won’t drop the perfect co-founder into your lap, but they will help you whittle your options down to a few strong front-runners. At the end of the day, selecting the right person comes down to who you feel that difficult-to-describe “click” with when you’re sharing your vision. Choosing an excellent co-founder isn’t an impossible task, and it certainly is an important one when it comes to building a company that will succeed under your and your co-founder’s leadership.

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

Founders’ most frequent pain points arise from pushing product development without speaking to their current customers. 

Initially, convincing founders to pause product development to conduct customer interviews is a tough sell. To them, it often feels like rendering their current ‘baby’ useless. But I know that ~40% of startups fail because they lack product-market fit, which means building something people actually want is the bare minimum. 

Ethnographic customer interviews

Personally, I love talking to users because I find people endlessly fascinating. But, as a founder, I found that formalizing our user interview process enabled us to quantify and track metrics of success and inform how we built Levantr.

Before building your product, start with ethnographic customer interviews. These are often just called customer interviews, but I like adding the adjective ‘ethnographic’ to it because that’s exactly what you are doing! You are trying to observe the users in their natural environment and see how they usually circumvent or deal with the problem you are trying to solve. 

Through these interviews, you’re trying to get a glimpse into how people behave and why, so you can create and test more accurate hypotheses about what your users actually want. 

Field Guide: Unlocking your users’ dream product with ethnographic customer interviews

Step 1: Define your target audience

There is a difference between people who would use your product and people desperate for it. You must find the latter for your MVP because they will become your cult following.

To start, consider the following:


At my startup Levantr—a collaborative travel planner—our customer segment was obviously people who like traveling, which is… a majority of the global population. So, we narrowed it down to people who enjoy planning, i.e., the people who create color-coded, multi-tabbed spreadsheets and send you SurveyMonkey forms to rally the crew. Of course, we all know at least one person like that.

These Type-A travelers not only travel frequently but think about traveling all the time. What does that mean? They follow travel blogs and are active in FB groups. They were our cult.

Step 2: Find and screen interviewees

First, look for interviewees on platforms like respondent.io, UserInterviews.com, and Askable. If your targets aren’t showing up on research platforms, try creating job postings asking your target profile to participate in a paid study or using social media platforms like LinkedIn to find target profiles to reach out to directly.

When offering money in exchange for interviews, you’ll inevitably attract some bad apples willing to lie to qualify for the study for the fee. However, you can weed them out using carefully crafted screener questions.

For example, here are some of the questions I used to screen Levantr interviewees:

  1. How many trips with friends have you organized? Do you usually create an itinerary?
  2. Will you be able to show an itinerary from your past travels during our call?
  3. How do you usually get ideas for your trip?
  4. Tell me about your favorite travel story.


Notice that #4 asks if they will show us their previous itinerary—this weeds out people who pretend to be active planners to qualify. I also ask how they usually get ideas to make sure we find people who think about travel frequently even if they are not traveling.

The last question is intentionally left open-ended to test how much detail they included. You want to find chatty interviewees who will quickly give you the most detailed insights.

Step 3: Conduct productive interviews

Conducting interviews remotely is more accessible, cheaper, and allows you to record your sessions. Recording not only helps you stay focused on the conversation without having to take notes, but investors love to see footage from your user interviews. Plus, you are not limited geographically, which removes any local bias.

The #1 rule of user interviews is to never ask them what solution they want directly. Instead, focus on understanding their problems, how they approach them today, and, most importantly, why. Your job is to observe and ask users to elaborate when they say something interesting.

For example, here’s how we structured our 1-hour user interviews:

  1. Set the scene — Provide context about your study and what you expect from them.
  2. Get the full picture — Ask them about who they are and the context of their life in general. What informs how they might currently approach your problem?
  3. Ask about their current solution — Have them tell you a story about the last time they had to tackle the problem. Are there tools they use? Who are the people they interact with during the process?
  4. Solve a hypothetical challenge — Ask them to talk you through their solution to step-by-step. Bonus points if they can share their screen and show you their process.


#3 is critical. It helps them travel back into a context relevant to your conversation and visualize the problem. Again, you’re triggering the emotions they felt during their last encounter, resulting in more accurate insights. This way, they’ll explain their process and show you how they perform the task.

Step 4: Apply feedback to MVP + MVB

Now that you collected your user feedback, you must decipher the implications and translate them into a product vision.

For example, here’s a list of steps I take to interpret interview insights while minimizing my own biases:

  1. Summarize each interview — Recap the interview as if you’re telling someone else the high-level conversation points—this will help neutralize your biases.
  2. Note key comments or insights — Beneath the summary, include comments that speak to what’s important to users or is currently solving the problem.
  3. Bring in outside perspectives — Review and evaluate those insights with an unbiased party to identify themes/patterns that illuminate underlying causes of the problem you’re trying to solve.
  4. Form multiple hypotheses — For each underlying cause, brainstorm multiple hypothetical solutions to avoid oversimplifying the problems themselves.


One of the recurring themes during Levantr’s pre-product ethnographic interviews was the importance of visuals in travel planning.

So, when we built the Levantr marketplace, we made sure that all the tiles/cards for our idea boards and itineraries included pictures. Plus, we knew that prioritizing the visual appeal of Levantr’s branding/marketing was critical to creating a sticky platform our customers love to use.

Context is key

To close, I’ll leave you all with my favorite example of ethnographic interviews gone wrong: “The Pepsi Challenge.” 

Pepsi had a campaign where people taste-tested Pepsi and Coke while blindfolded, then indicated their preference. And surprise, surprise, Pepsi was the winner. Meanwhile, Coke was extremely worried because their internal studies showed similar results. So, in response, they created ‘New Coke’ to mimic Pepsi’s sweeter taste and introduced it to the market with great confidence. 

‘New Coke’ failed spectacularly, and Coke’s customers were pissed. But why?

The sip tests didn’t take into consideration the environment in which people drink Coke. People don’t take just one sip when drinking soda; they drink a whole can of Coke with a meal, at a sporting event, at the movies, etc. In the actual use-case contexts, people prefer the crisper taste of Coke over the saccharine sweetness of Pepsi or ‘New Coke’—except in small, sippable doses. The theory is that a home-use test would’ve yielded a very different outcome. 

Coke recovered from the ‘New Coke’ fiasco because they’re a well-established brand with loyal customers and money allocated for trial-and-error product development. But startups don’t have the same luxury. That’s why investing a few hundred bucks now to talk to your target audience through a contextual inquiry. 

So, what can founders learn from Coke? First and foremost, the quality of your user research will determine your ability to build the product of your target audiences’ dreams. How you ask your research questions matters: carefully consider your word choice and the context of both your interviewees and the problem you’re trying to solve. Finally, listen to your customers before rolling out a ‘New Coke’ product development that nobody wants.

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

As an investor, I’ve seen a lot of startup pitches—the good, the bad, and the ugly. And as a former founder, I feel for them. I know how daunting it can be to take the vision in your head, condense it into a clear explanation, and get others to quickly believe in it too. Early on, I also struggled to succinctly communicate the vision I had for my company. 

At Outlander VC, I combine my experiences as a founder and investor to help our portfolio companies perfect their pitches. These are some of the best tips and tricks I’ve learned along the way to prepare, perfect, and present your pitch so that investors want to hear it. 

#1: PREPARE to showcase the founding team’s intelligence, vision, character, and ability to execute

When you’re raising capital in the early stages, there isn’t much of a company to pitch yet. It’s just a few folks, an idea, and maybe an MVP. You probably don’t have customers, users, or meaningful quantitative data to inform the investment decision.

Early-stage investing decisions come down to evaluating how the founders answer the following questions, based on Outlander’s Founder Framework model:

Ultimately, early-stage investors are looking for a founding team worth betting on. Early-stage founders with compelling answers to the above questions demonstrate they have the intelligence, vision, character, and ability to execute necessary to build on their thesis and scale it into an industry-disrupting powerhouse.

#2: PERFECT by hitting “record” first; then practice, practice, practice

Helping early-stage founders perfect their pitches, I’ve noticed a common disconnect: passionate founders who eat, sleep, and breathe their startup perceive the cadence of their pitch as clear, confident, and compelling—but investors often hear it differently.

For example, I was recently working with a founder on his pitch. He has the big vision and passion necessary to convince investors, but his delivery needed fine-tuning. Seeing is believing, so I suggested he record his next pitch and send me the recording.

The next time we spoke, he told me that he’d realized, watching the recording, that he’d had no idea how his pitch sounded. With the recording, he could self-critique and correct every part of his delivery he didn’t like. He could sit on the other side of the pitch deck and, for the first time, see exactly what his potential investors would see.

We decided to take this exercise a step further. Instead of booking time with peers to get their feedback, he sent them links to his recorded pitch. Recording his pitch practice worked well for several reasons:

Recording yourself isn’t novel—it’s a time-tested tool, and it’s still highly effective. Plus, with new WFH tools like Loom’s simultaneous camera, microphone, and desktop recording technology, sharing a virtual pitch has never been easier. If you want to perfect your pitch, consider tapping “record” first!

#3: PITCH starting with these three questions

As I said, I’ve watched a lot of pitches. The most painful to watch are those where the investor struggles to understand what the founder is trying to communicate. But I’ve helped founders whose pitch crashed and burned in the morning regroup, adjust their approach, and nail the same pitch a few hours later.

The difference? At the beginning of the second meeting, the founders sought to understand their audience by asking a few simple questions, which allowed them to deliver the pitch in the way the audience preferred. The change was small but powerful.

Here are a few questions founders can ask to understand their audience:

Understanding the audience goes a long way toward helping founders communicate effectively and gain support. The questions above will help accomplish that, but it’s by no means an exhaustive list. Plenty of other questions would also work. Regardless of what you ask, I’d limit it to two or three questions.

Test your perfected pitch at OutPitch 2.0

Now that you’ve perfected your pitch, we want to see it! Here’s what you need to know:

Outlander VC is inviting the most innovative early-stage tech startups in the United States to out-vision, outsmart, and outpitch the competition at OutPitch 2.0! Apply now to compete for $100,000 investment from Outlander VC during the live event on December 7, 2021.

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

On April 23, 2005, ‘Me at the Zoo’ was the first video ever uploaded to a then little-known site called Youtube. This moment was an inflection point that precipitated the explosions of video-first social media services over the next 15 years: TikTok, Instagram, Snapchat, etc. Moreover, it was a harbinger of much broader changes to come.

COVID-19 altered the world in many ways; being locked in our homes forced us to rethink how we communicate, work, and socialize. It has also led to a tectonic shift in how businesses operate. COVID has been the accelerant that has led to the decentralization of the global workforce. 

Enterprises have been forced to change centuries-old practices of having people come into an office to work. And video is the medium that enabled them to do so. 

This is not a discrete or temporary event. As the pandemic recedes and the world begins to regain an air of normalcy, many businesses have been compelled by their employees to rethink the very concept of ‘the office.’ The ideas put forth by managers for generations—such as productivity tied to the physical place of work—have now been debunked as relics of the industrial age. This shift did not transpire out of some charitable concern for employee welfare but, instead, driven by sheer economics and by employees refusing to work in conditions that negatively affect their lives without clear benefits to the productivity of their employers. 

With video now acting as the conduit for productivity, what’s next? We believe the answer lies with automation. The trend for automating work is not new, but video provides ample opportunities for doing it in novel ways.

Robotic process automation is the early precursor of this ethos. With the automation of basic digital workflows and no-code environments, the automated back-office tasks increase productivity and free employees of time-consuming, remedial tasks. Companies such as UI-Path, Automation Anywhere, and others have trailblazed no-code automation tools that enable workers to automate their daily tasks. Much like the wheel or the steam engine, these tools shift the burden of work off of people onto machines. However, while videos have become ever more present in work, leveraging the information trapped within them has not been possible until recently.

Artificial intelligence (AI) provides the key to unlock this potential in video.

The rapid development of machine vision and similar technologies propelled by the expansion of deep learning systems has primed the world for automations that use video as a proxy for many tasks that otherwise would be impossible to capture. 

From sales information in Zoom presentations to quality control on semiconductor manufacturing lines, video data is ripe with hooks that can be used as proxies for automation.

If we can tap into the unstructured information stored in these videos and automate processes around it, we could automate even more of our workload and free employees of even more time-consuming, repetitive tasks.

Utilizing video data has never been more relevant. COVID-19 not only reframed the way we work but also the way we consume information on a day-to-day basis. Being quarantined in our homes forced us to consume our news, connect with the world, and seek entertainment not through the lens of personal interaction but primarily through videos broadcasted live and published on social media.

This drastic change in information consumption has led to a media landscape ripe for “disinformation” to propagate and pass into our society completely unchecked. Through a combination of state-sponsored misinformation and individual bad actors, it’s become incredibly difficult to understand what is true and what is not, and video is the most compelling piece of many disinformation arcs. It’s becoming increasingly easy for a maligned actor to edit a piece of video, remove valuable context, or share a video post from an entirely separate location with a leading caption and have their post go viral.

To address this type of disinformation, the ability to attribute provenance at scale is crucial. Consequently, the ability to collect live, social, and archival content is necessary for anyone attempting to validate whether or not a piece of content is original, manipulated, or has appeared across other channels. Finally, there is a need for automated tools to analyze and uncover strategies, patterns, and methods used by these actors in their narratives. 

Large platforms such as Facebook, Google, and Microsoft have already begun developing in-house tools for tackling things like DeepFakes. Smaller organizations, however, are lagging behind in this effort, as they lack the expertise required to develop such systems. 

At Vidrovr, we work with organizations to bridge this gap and utilize their video data to uncover patterns and automate business processes.

For example, we developed a solution for the Association for Securing Democracy’s Hamilton 2.0 Dashboard to analyze large amounts of media content—both text and video—to comprehensively look at the information landscape created by state-sponsored media outlets. These types of technologies are the first step in a long journey towards a robust understanding of the current media landscape.

These are the problems that we at Vidrovr are focused on solving. We build AI tools for unlocking insights trapped in unstructured multimedia and video to drive data visibility, understand the video information landscape, and enable business automations. Learn more about our solutions at https://vidrovr.com.

We’re always looking for partners to help on this journey, so please reach out to our team at contact@vidrovr.com. Plus, we’re hiring for our marketing, sales, and engineering teams! If you think you might be a good fit or want to learn more about our vision for the future, we’d love to hear from you.

Forming a new startup is an exciting time filled with optimism and potential. Finding the right people for your team, landing some early investors, and building out your product are all thrilling milestones. But just as important (if not quite as thrilling) are some key legal fundamentals that you’ll have to nail early on.

Every startup needs to get these tasks right at the beginning; failure to do so will lead to difficult, protracted, and costly problems.  I should know, my first job after being a partner at a big law firm was cleaning stuff up at Oculus, so it could do its Series A.  

Despite legal forms you can find on the internet or from DIY websites such as Clerky promising to make forming a startup easy, more often than not, these seven items are not done right:

  1. Setting Up Your Cap Table This could be called understanding Venture Economics 101: how to split up the equity among the founders, how much to allocate to a stock incentive plan, how to put your money into the company, and how much dilution you really can or want to have before you do a round of equity financing. 
  2. Forming a Delaware CorporationIf you are going to raise venture capital, you need to form a Delaware Corporation. You would be surprised how many Nevada, California, Utah, New Jersey, and other states limited liability companies and corporations we have had to convert into Delaware corporations. These conversions are always costly and have some degree of complication. Venture capitalists invest in Delaware corporations for two primary reasons: 1) C Corps are not “pass-through entities,” which allows the business’ losses to be used to offset future revenue for tax purposes, and 2) Delaware has the most developed body of corporate law in the country and a very specialized system of courts and judges, which is why the National Venture Capitalist Association (NVCA) bases their financing templates on Delaware Law. So, if you want to raise venture capital, you need to start with a Delaware C Corp.
  3. Founders’ Stock Purchase Agreements and 83(b)s You need an agreement to purchase the stock in your company, and if you have more than one founder, you will want the stock to vest in case someone leaves. This is done through a stock buyback and 83(b) election.  We see everything here from people not even having an agreement to purchase the stock to completely missing the 83(b) election, which creates real tax problems.  We once started a Series Seed and the founders were worried about the stock incentive plan being too big, but when we checked their paperwork, they had not even granted their own shares to themselves, let alone set up a stock incentive plan. Recently we had a startup that received a term sheet for roughly $2,000,000, but because they didn’t file their 83(b) on time, each of the founders would’ve needed to pay taxes on the gains of the value of their stock. In this case, that gain would have added up to a few $100k. Needless to say, the investor didn’t want their money being used to pay off each founder’s tax liability, which led to the deal blowing up. Filing an 83(b) on time is critical and could mean the difference between raising $2,000,000 and raising nothing.
  4. Getting Founders’ and Key Employees’ Intellectual Property Into the Company We once represented a football-game tech startup for one of the greatest quarterbacks of all time, and he had failed to license in the rights to his name and likeness for the virtual-reality game branded on his name.  You can’t make up some of the stories and scenarios that we have encountered.  But if the company does not own the intellectual property, then there is nothing there.
  5. Establishing a Stock Incentive Plan (SIP), Pricing the Common Stock Properly and Issuing Options or Restricted Stock Properly Employees, contractors, and advisors receive stock from the SIP, and often, startups use these options to compensate for a lower salary. What makes options so valuable to early employees is that their stock is valued at nearly zero since the company is not profitable. This could lead to a huge payday for these employees if the company is successful. However, if you don’t adopt the SIP at the beginning and you begin to generate revenue, you’ll need to conduct a 409(a) Valuation to calculate the value of that stock. This leads to higher valued stock, which is bad for employees receiving options. For example, if an employee had 100,000 shares valued at $0.00001, the exercise price (the price paid to own the options you received) would be $1. If those 100,000 shares were valued at $1, that employee would then have to pay $100k to exercise those options. The difference between $1 and $100k is glaring and a difference that most people can’t afford to pay. 
  6. Financing Properly With SAFEs and Convertible Notes In the early days, you will need capital and need it quickly, so financing the company with SAFEs or Convertible Notes instead of pricing the common or issuing preferred stock can save time and money and also avoid problems with raising the exercise price of the stock options.  Again, we have had founders price the common with sales to friends and families (which messes up the stock incentive plan) or lend the company a lot of money and have an investor get upset when that loan was repaid after a round of equity financing.
  7. Hiring Contractors and Employees Correctly This is critical, but again, I kid you not, we cleaned up a five-year-old tech company where the CTO, a contractor, had never signed a Confidentiality Invention Assignment Agreement (CIAA). Then, when a new investor asked him to sign a CIAA, the CTO held the company hostage for a month with salary demands as the company did not own its tech stack.

How do you accomplish the 7 things every startup needs to get right? 

We have found that systems, processes, knowledge and counseling, good decision-making – and then recording decisions in such a way as to be able to automatically translate those decisions into legal paperwork – can solve 90% of these problems (and avoid $100,000 cleanups later). 

In broad terms, you’ll need: 

As you see, it’s a lot of work to take on those seven things, especially if you’re a first-time founder – but they’re absolutely critical to your future success. For that reason, we put together StartupProgram.com, or SUP, so that our clients can efficiently and cost-effectively get these nuts-and-bolts items checked off their to do lists. We’d love to help your startup, too. 

Join us on 6/9 at 12 pm ET for the first of our quarterly Legal Lab learning series and our monthly, 1:1 Legal Lab Office Hours with Dan Offner! 🧪

© Outlander VC. 2022.