Ever wondered how Scale AI grew to $14B by mastering government contracts? In this candid panel discussion, we sit down with Scale’s Director of Public Sector Deployment Strategy and veteran defense specialists to reveal their playbooks for success.
Why Watch:
Featuring Scale AI’s Shaliya Dehipawala, Frontera Group’s Thomas Williams, and Washington Office’s Evan Burfield, this is the guide we wish existed for every founder eyeing the federal market.
Watch now to unlock the full federal playbook.
Welcome to another deep dive into the minds of venture capital leaders who are shaping the startup ecosystem. In our latest Venture Visionaries conversation, we sat down with Alexa Von Tobel, founder of Inspired Capital, to unpack her insights on what truly makes a founder—and a startup—successful.
With a background as a founder herself (LearnVest, acquired by Northwestern Mutual for nearly $400 million) and now managing almost $1 billion in investments, Alexa brings a unique perspective grounded in real-world entrepreneurial experience.
1. Obsession is the Founder’s Secret Weapon
Alexa believes the biggest pitfall for founders is building a business they don’t genuinely want to think about every day for the next 15 years. Her advice? If you’re not obsessed with the problem you’re solving, don’t start the company.
For Alexa, this personal obsession was deeply personal. After losing her father, she became passionate about democratizing financial planning—a mission that fueled LearnVest. Without that obsession, it may never have become one of the largest FinTech acquisitions of the decade.
Founder Takeaway: At Outlander, we love obsessed founders who are consumed by a problem–who see a future state that needs fixing and that you are the one to do it. Your startup should solve a problem that keeps you up at night. When the going gets tough, passion isn’t just motivational—it’s fundamental to your persistence.
2. Adaptability Over Resilience
Alexa champions adaptability. She believes the most successful founders aren’t just those who survive challenges, but those who thrive because of them.
Drawing from her podcast interviewing over 260 top founders, she’s observed a common trait: these entrepreneurs view stress as a catalyst for growth. Like Darwin’s principle of survival, it’s not the strongest who succeed, but those most adaptable to change.
Founder Takeaway: At Outlander, we love founders who have demonstrated resilience. But more important than having endured hardship is showcasing the ability to learn from it and adapt to ever-changing environments. Your ability to pivot and learn quickly may be the most valuable asset in your founder journey.
3. Capital Efficiency is Your Competitive Advantage
In today’s market, Alexa emphasizes the critical importance of being a smart capital allocator. The best founders understand that a business is essentially a machine: you put a dollar in with the expectation of generating multiple dollars in return.
She warns against unnecessary spending, especially in early stages. The most impressive founders are those who can turn on meaningful traction with minimal capital, demonstrating “scrappiness” that becomes part of the company’s DNA.
Founder Takeaway: Every dollar matters. Be strategic about resource allocation and prove you can create value with constraints.
4. The DNA of Startup Success
Alexa draws a powerful analogy from her experience founding LearnVest during the 2008 recession. Founders who start businesses during challenging times develop a different operational DNA—they learn to run at “50 miles per hour” when others might be moving at “6 miles per hour.”
This forged resilience becomes a core part of the company’s culture, creating teams that know how to operate efficiently and effectively, even when resources are limited.
Founder Takeaway: Your early-stage constraints can become your greatest strength. Embrace the challenge and let it shape your company’s culture.
Final Thoughts
Inspired Capital’s approach, much like our Founder Framework at Outlander VC, is about backing people, not just business models. It’s about finding founders who are relentless, adaptable, and deeply committed to solving meaningful problems.
For founders reading this: obsess over your mission, embrace challenges, be capital-efficient, and never stop learning. Your journey is just beginning.
Stay inspired and outlandish and, as always, be sure to pitch our team your vision at: www.outlander.vc
You can learn more about Inspired Capital at https://www.inspiredcapital.com/
Watch the full interview:
Welcome back to Venture Visionaries, a series from Outlander VC where we dive deep into what distinguishes top investors and explore their unique perspectives on the startup ecosystem.
Join us as we engage with some of the most influential figures in venture capital, uncovering the strategies and insights that have shaped their success and learning how they navigate the evolving world of investing.
From investment philosophies to future predictions, these conversations will inspire entrepreneurs and anyone curious about the venture capital space.
This month, we had the privilege of sitting down with Tim Young, founding partner of Eniac Ventures (Eniac’s portfolio includes AirBnB, Headspace, Hinge, and more). In our conversation, Tim offered his perspective on what sets founders and investors up for success, rooted in his experience on both sides of that equation.
Tim’s unique, grounded outlook on how to identify promising teams and support them through the ups and downs of building a company are what have helped make him (and Eniac) wonderful investors that we love to partner with at Outlander.
You can watch the full conversation here!
And be sure to sign-up for our Fall 2024 portfolio showcase!
Here are three key takeaways from the conversation:
Integrity isn’t optional for Tim. He stresses that while founders might have many areas to grow or develop, trustworthiness is too easily shattered and difficult to repair for him to back a low-integrity founder. The ripple effect is massive: a founder lacking integrity can sabotage their team, erode investor confidence, and ultimately derail the entire company.
Often, integrity (and another key character trait we look for: grit) reveals itself in moments of adversity. How have challenges been handled in the past? Are you an ego-driven leader or a servant-leader who leads by example, respects their team, and constantly builds trust? Ultimately, as Paige expressed in the conversation, “power doesn’t come from rank; power doesn’t come from mission.” It comes from the earned respect of your team, your investors, and your customers.
Tim Young has a simple yet profound question he asks himself before committing to an investment: Would I leave my job and work for this person? It’s a gut check that cuts through all the hockey-stick financial projections and product demos to get at the heart of what matters—leadership.
This is something that we, at Outlander, call being an infectious evangelist: having the storytelling charisma and leadership ability to not only win over your co-founders, but team members, investors, and customers.
This question isn’t just about the founder’s vision; it’s about their ability to inspire trust and loyalty. And we love Tim’s gut check: When Paige was an early investor in Lyft (then Zimride), he described that feeling of wanting to not just get involved as a check-writer, but to actually go and join the team in the mission. Fast-forward 10 years and that litmus test checks out, with Lyft surpassing $5.22B market cap.
Moral of the story for founders: hone your leadership and evangelizing skills. Because if investors can’t see themselves willingly joining a founder’s team, it may be a sign that other talented individuals may feel the same. A great product can only go so far if the founder lacks the ability to attract and retain top talent.
Tim Young is realistic when evaluating founders—he knows no one is perfect. In his words, “There are no 10/10 founders.” Every founder has areas of strength and weaknesses, and as an investor, it’s essential to recognize this early. What matters isn’t having a flawless skill set but having the self-awareness and coachability to improve over time.
For Tim, identifying gaps in a founder’s abilities isn’t a dealbreaker. Instead, it’s about understanding where those gaps are and whether the founder is willing to address them. Are they open to bringing on team members who can complement their weaknesses? Are they willing to seek mentorship or guidance where they lack experience? Having a blind spot and being unwilling to hear about it can make it hard to reach conviction.
Savvy investors know to mostly stay out of the way except when necessary, so chances are that if you are working with an investor who has a track record like Eniac or Outlander, when they are pulling you aside, it’s important.
Final Thoughts
Tim Young’s approach to investing emphasizes a deep commitment to understanding founders as people. It’s a belief that we share at Outlander and is the driver of our Founder Framework. For us, it’s not just about metrics or market opportunities—it’s about asking the right questions and backing people that we believe in.
Watch the full conversation between Paige & Tim here.
Stay Outlandish and, as always, be sure to pitch our team your vision at: www.outlander.vc You can learn more about Eniac at www.eniac.vc
Despite the long-documented gender gap in funding female* founders, there is good news for the ecosystem in the recent rise in women-led venture capital (VC) firms.
In 2023, women-led VC firms raised a record $3.5B in 2023 (up $500M from 2022). This still only accounts for roughly 3% of all venture funding raised in 2023, but represents a significantly promising step for the entire startup ecosystem.
Especially because the indication thus far is that women-led funds are more likely to invest in diverse founders, which research indicates actually correlates with better financial performance.
Here are some quick facts regarding female* founded companies for your next pitch:
We’ve put together a short list of 24 incredible women-led VC firms (24 for ’24!) that should absolutely be on your radar. There are many more, so be sure to tag them on our LinkedIn post to help more female* founders find great investors!
And, as always, be sure to submit your venture for our investment team here!
*female & female-identifying
Sources: VCJ, Pitchbook, BCG, Forbes
Featured Partners: Leura Craig and Bailie Salk
Highlighted Investments: Gusto, Lyft, Klarna, Wish, Scale, Andela, Postmates
Outlander VC is a leading venture capital firm with a remarkable track record, including 17+ unicorns among its ~150 portfolio companies. Under the leadership of Leura Craig, Outlander has become a top-decile performer and is actively deploying capital from its third fund. The firm is notable for its commitment to diversity, with half of its investment partners being women and 62% of its portfolio having diverse founders.
How to Apply: Fill out this form
Featured Partners: Susan Lyne, Nishua Dua
Highlighted Investments: Zola, The Mom Project, Lola, Winky Lux, Oova
BBG Ventures, under the leadership of Susan Lyne and Nishua Dua, invests in early-stage startups with at least one female founder. They are on Fund IV and actively hearing founder pitches.
How to Apply: Fill out this application
Featured Partners: Theresia Gouw, Lauren Kolodny
Highlighted Investments: Bilt, Gusto, Chime, Clara, Discord
Acrew Capital is a powerhouse in early-stage venture investing, led by Theresia Gouw and Lauren Kolodny. The firm is known for its strategic investments in fintech, cybersecurity, and consumer tech, driven by a leadership team that brings a wealth of experience and a commitment to diversity.
How to Apply: Contact us button on their website
Featured Partner: Aileen Lee
Highlighted Investments: Docsend, The League, Crunchbase, Enrich, Guild
Cowboy Ventures, led by Aileen Lee, is known for its strategic investments in software-focused startups. Aileen Lee’s experience and leadership have made Cowboy Ventures a key player in the early-stage venture capital arena.
How to Apply: Reach out directly (contact in footer)
Featured Partner: Anu Duggal
Highlighted Investments: Zola, Bentobox, Wayup, Winky Lux, Fable
Female Founders Fund, led by Anu Duggal, is a leading source of capital for women entrepreneurs. The firm’s investments span a variety of sectors, all united by their focus on female leadership and innovation.
How to Apply: Fill out this application form
Featured Partner: Leslie Goldman Tepper
Highlighted Investments: DressX, Fundid, The Good Patch
The Artemis Fund is a seed-stage fund focused on tech startups in fintech, commerce, and care sectors. Leslie Goldman Tepper’s leadership has positioned the firm as a key player in supporting diverse founders who are building the next generation of transformative companies.
Fill out this form
Featured Partners: Theresia Gouw, Jennifer Scott Fonstad
Highlighted Investments: Baublebar, Gusto, HotelTonight, TheRealReal
Aspect Ventures is a Series A-focused (selected seed participation) firm whose team has funded over 100 companies and participated in 350+ follow-on investments.
How to Apply: Contact via email (listed on their website)
Featured Partners: Dayna Grayson, Rachel Holt
Highlighted Investments: Uber, Copia, Incremental, Verve, Telegraph
Construct Capital, co-led by Dayna Grayson and Rachel Holt, focuses on early-stage investments in industries like manufacturing, logistics, and supply chain. The firm’s leadership team brings deep expertise to their investments, driving innovation in these foundational sectors.
How to Apply: Reach out via email (website footer)
Featured Partner: Kirsten Green
Highlighted Investments: The Farmer’s Dog, Chime, Ritual, him&hers, Oura, Glossier
Forerunner Ventures, under the leadership of Kirsten Green, specializes in investments in e-commerce and consumer brands.
How to Apply: Fill out this application form
Featured Partner: Roseanne Wincek & Renata Quintini
Highlighted Investments: Warby Parker, Masterclass, Dollar Shave Club
Renegade focuses on early-stage investments in AI/ML, Vertical SaaS, Enterprise, Consumer, FinTech, InfraTech, and more.
How to Apply: Check their website for updates on investment opportunities or reach out directly through their contact page.
Featured Partner: Rebecca Kaden
Highlighted Investments: Etsy, Twitter, Duolingo, Coinbase, Kickstarter
Union Square Ventures is a NYC-based VC, investing on the edge of large markets being transformed by technological and societal pressures.
How to Apply: Union Square Ventures prefers warm introductions, but they are also receptive to pitches sent via email (see website footer).
Featured Partner: Annie Kadavy
Highlighted Investments: Stripe, Snowflake, HashiCorp, Nubank
Redpoint invests across consumer and enterprise and they have partnered with thousands of inspiring entrepreneurs over the past two decades.
How to Apply: Redpoint Ventures accepts warm introductions, but you can also reach out via their website.
Featured Partner: Clara Sieg
Highlighted Investments: sweetgreen, DraftKings, TemperPack, Scopely
Revolution Ventures, HQ’d in Washington, D.C., invests in companies outside traditional tech hubs through their family of funds – Revolution’s Rise of the Rest Seed Fund, Revolution Ventures, and Revolution Growth – Revolution partners with entrepreneurs at every stage of the entrepreneurial lifecycle.
How to Apply: Networking and referrals are the best ways to approach them!
Featured Partner: Mary Meeker
Highlighted Investments: Canva, AirBnb, Doordash, Duolingo, Instacart, Clear, Peloton
Mary Meeker’s Bond Capital specializes in late-stage growth investments in high-potential companies, particularly those leveraging technology to scale rapidly.
How to Apply: The best approach is through a network referral!
Featured Partner: Mar Hershenson
Highlighted Investments: DoorDash, Gusto, Branch, Guardant Health
Pear VC is a seed-stage venture firm led by Mar Hershenson and Pejman Nozad, focusing on partnering with founders from the earliest stages of their journey.
How to Apply: Pear VC encourages founders to connect via their online application form.
Featured Partner: Aubrie Pagano
Highlighted Investments: Compass, Firstbase, Animoca, Classpass, Imperfect Foods
Alpaca VC, led by Aubrie Pagano, invests in companies reshaping the built world, leading rounds in real estate and commerce.
How to Apply: Send them an email (Listed in their footer)
Featured Partner: Kate McAndrew
Highlighted Investments: Figma, Notion, Clubhouse, Threads
Kate McAndrew leads Baukunst, a venture firm that invests in creators, builders, and entrepreneurs with a focus on creative and impactful technology & design.
How to Apply: Network introductions work best, but you can also reach out via email (see website footer)
Featured Partner: Dana Settle
Highlighted Investments: Venmo, Scopely, TheRealReal, Braintree, Boxed, Bumble
Greycroft focuses on early to growth-stage investments in technology companies across the globe with the potential to transform sectors.
How to Apply: Network introductions work best!
Featured Partners: Stephanie Palmeri and Melody Koh
Highlighted Investments: Grove Collaborative, ThredUp, Skillshare, Whoop, Attentive
NextView makes initial pre-seed & seed stage investments (checks between $400k – $4m) into software and AI companies redesigning the everyday economy.
How to Apply: The best way to get in touch is through a referral, but you can also contact through their website!
Featured Investor: Monique Woodard
Highlighted Investments: Pamper, Eli Health, mama, Bright, Serif
Cake Ventures invests in pre-seed & seed stage companies that reflect demographic change: aging & longevity, increased spending power of women, and the shift to majority-minority.
How to Apply: Apply here.
Featured Partner: Jesse Draper
Highlighted Investments: Everlywell, Inked, Metropolis, Live Tinted
Halogen Ventures is an early stage venture capital fund investing in consumer technology companies led by women and based in Los Angeles.
How to Apply: Apply here.
Featured Partner: Shadi Mehraein, Rebeca Hwang, Christina Brodbeck
Highlighted Investments: Athena, Honeybook, Ritual, Mayvenn
Rivet Ventures invests in companies where women are the key consumer demographic, focusing on companies with products or services that cater to women’s needs.
How to Apply: Contact via email (listed here).
Featured Partner: Shripriya Mahesh & Sara Eshelman
Highlighted Investments: Telo, Eli, Remark, Oova
Spero Ventures invests in founders building mission-driven technology companies in three focus areas: wellbeing; sustainability; learning, work, and play. They prefer to lead or co-lead a $3M-$10M round (late seed or Series A), typically writing checks from $2M – $4M.
How to Apply: Network introductions work best!
Featured Partner: Mercedes Bent
Highlighted Investments: OutSchool, Flink, Stori
Mercedes joined us a couple months ago for one of our most highly-attended Venture Visionary interviews. Lightspeed has added multiple female investing partners in the last few years. They love backing founders early and support from seed through Series F and beyond.
How to Apply: Network introductions work best!
Global geopolitical tensions have reached their highest levels since WWII. 92 countries are currently involved in conflicts beyond their borders and the Global Peace Index has measured “peacefulness” declining in nine out of the last ten years. The push to decrease human casualties, combined with recent technological advances, has created a new environment that has governments turning to the historically innovative private sector to stay competitive and defend against potential threats.
In the last three years alone, U.S. venture capital (VC) funds have injected over $100B into defense-tech companies. And while Department of Defense (DoD) contracts have typically been awarded to established players like Lockheed Martin, RTX, Northrup Grummon, and others, DoD innovation organizations (e.g., DIU, AFWERX, NavalX, and more) are increasingly working with startups to source innovative solutions.
As founders consider investment partners for their defense or dual-use technology ventures, we’ve put together a list of top funds to consider. And if you are an investor and think you should be on this list, contact us!
Outlander VC
About: Top decile-performing generalist pre-seed fund, led by U.S. Marine Corps veteran and defense & intelligence-tech founder Paige Craig, investing at the earliest stages (often first check in).
Stages: Mostly Pre-Seed to Seed
Notable Investments: Scale, ID.me, SpaceX, REGENT, Skyways, Havoc, Vidrovr, Next Stage
How to Apply: Apply directly through this form
Moonshots Capital
About: With 13 unicorns and 27 total exits, Moonshots is a veteran-led seed & early Series A fund investing in bold founders.
Stages: Seed to Series A
Notable Investments: Slack, LinkedIn, Carta, ID.me, Red 6
Application: Submit proposals through their website
Point72 Ventures
About: Point72 Ventures is the VC arm of Point72 Capital and has a team that includes Managing Partner Dan Gwak, a U.S. Marine Corps veteran turned investor.
Stages: Pre-Seed to Growth
Notable Investments: Shield AI, Vannevar Labs, STOKE Space, Saronic, REGENT
How to Apply: The best way to be considered is to get an intro to a relevant investing partner, but you can also email directly to ideas@p72.vc
Alumni Ventures
About: A top-quartile performing venture fund that also invests in defense & dual-use technologies.
Stages: Pre-seed to Growth
Notable Investments: Unstructured.io, Red 6, Picogrid, Antares Industries, Edgescale AI, Sphere Semi
How to Apply: Apply directly through this form
Decisive Point Ventures
About: A VC fund focused on making early-stage investments in technology for government, public safety, and defense.
Stages: Predominantly Seed & Series A
Notable Investments: Scout Space, Radiant, Aloft, Firehawk Aerospace
How to Apply: The best way to be considered is to get an intro to a relevant investing partner, but you can also email directly to info@decisivepoint.com
First In Ventures
About: Veteran-led fund investing in security tech solutions across commercial, military, or intelligence sectors.
Stages: Predominantly Pre-Seed & Seed
Notable Investments: Anduril, Shift5, RedOwl, Syncurity
How to Apply: Fill out this form
RTX Ventures
About: Venture capital division of RTX (formerly Raytheon Technologies). Led by Daniel Ateya
Stages: Predominantly Seed & Series A
Notable Investments: Ursa Major, Hermeus, EnCharge AI, Tomorrow.io
How to Apply: Contact through the RTX Ventures website
In-Q-Tel
About: CIA-contracted investment fund, designed to source innovative information technology solutions for the Central Intelligence Agency. Led by Steve Bowsher.
Stages: Seed, Series A, sometimes later
Notable Investments: Palantir, Databricks, MongoDB, Anaconda
How to Apply: Apply directly through this form
Shield Capital
About: Former DoD Defense Innovation Unit leader and former Symantec CEO Michael Brown became a partner at Shield Capital in 2023 to invest in dual-use defense, cybersecurity, and space companies.
Stages: Seed to Series B
Notable Investments: Nexla, Apex, ASI, Rebellion
Application: Apply directly through this form
a16z’s American Dynamism
About: Andreesen Horowitz’s American Dynamism practice invests in founders and companies that support the national interest: aerospace, defense, public safety, education, housing, supply chain, industrials, and manufacturing.
Stages: Seed to Growth
Notable Investments: Anduril, Apex, Hadrian
How to Apply: Reach out or get an intro to a relevant investing partner
Silent Ventures
About: Early stage venture firm that invests in exceptional founders building unrivaled aerospace, defense, and national security companies.
Stages: Predominantly Pre-Seed & Seed
Notable Investments: Hadrian, Armada AI, Firestorm
How to Apply: Apply or reach out on LinkedIn
Lockheed Martin Ventures
About: The VC arm of defense giant, Lockheed Martin, doubled its fund commitment from $200M to $400M in 2022, rooted in its belief that the most dynamic defense innovations will come from startups.
Stages: Pre-seed to Growth
Notable Investments: Elroy Air, Hawkeye 360, Heilcity Space, X-Bow
How to Apply: Apply directly through this contact form
Champion Hill Ventures
About: Led by a former infantry and combat engineer officer in the US Marine Corps, Champion Hill has invested in some of the hottest defense tech & space startups.
Stages: Pre-Seed to Seed
Notable Investments: SpaceX, Anduril, and Umbra
How to Apply: Get an intro to or reach out to Managing Partner Josh Manchester.
Insight Partners
About: Generalist VC, increasingly making investments in defense-focused startups
Stages: Pre-seed to Growth
Notable Investments: Rebellion, Tenable, Digital Harbor
Application: Apply through their website
Lux Capital
About: Science & technology venture fund, making strategic investments to protect America’s economic security.
Stages: Any stage
Notable Investments: Anduril, Hadrian, Saildrone
Application: Connect with (or get introduced to) a relevant investing partner
Starburst Ventures
About: Aerospace & Defense investor for America and its allies.
Stages: Seed to Series A
Notable Investments: Strong Compute, Outpost, Aerocloud
Application: Join one of their accelerators or submit proposals through their website
Scout Ventures
About: Early-stage venture capital firm that invests in frontier technologies built by founders from the military, its intelligence community, and national research labs.
Stages: Seed to Series B
Notable Investments: ID.me, Radical, Voyager Space, Tomahawk Robotics
Application: Submit proposals through their website
For founders of dual-use start-ups seeking funding, Outlander VC offers unparalleled expertise and strategic support. If you are a defense technology start-up seeking funding and strategic guidance, apply to Outlander VC today.
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!
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:
In the real world, this could look something like:
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?
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!
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.
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.
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.
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!
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!
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.
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:
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
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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:
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.
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.
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.
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.
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.”
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.