Dan Olsen

Building Products in Startups: Lesson #2 As entrepreneurs, we often gravitate towards what we naturally excel at or enjoy. Not everyone is a born salesperson, but until you've heard "NO" enough times, you haven't really tested your product and your own resiliency. Resiliency is especially important when you are prospecting for potential clients. In short: EMBRACE THE "NO" TO FIND THE "YES" — AND NEVER STOP SELLING YOUR PRODUCT. Building a startup also means pushing boundaries. As founders, many of us aren’t trained sales professionals, but here's the truth: selling is a muscle you need to exercise regularly. Each "no" is an opportunity to understand your market better, refine your pitch, and find your path to "yes." Here are some additional observations to date: Learn to Love Objections. The tough questions from potential clients are golden opportunities. They force you to think critically and refine your product's value proposition. If you only hear praise, it's time to dig deeper.  Praise makes me nervous! Stay in Sales Mode. No matter who joins your team, founders should remain close to customers and drive top-line sales. Relying solely on others to sell your product can be risky. Keep Iterating on Your Sales Pitch. Don’t settle for a pitch that works once. Iterate, adapt, and evolve.  Don’t Delegate. You may be tempted to delegate sales to a 3rd party who has “access” and “special sauce” - do it yourself at first. Refine Your Ideal Customer Profile & Buyer Persona. Do this until you hit on a conversion rate within the accepted range for your industry segment. By the way, even if you dream of a product that sells itself (and that should be the goal), the reality is, few products do. 🤷‍♂️ Whether you're a natural salesperson or not, selling is a fundamental skill in the startup world. What sales challenges and lessons can you share? Happy Selling! 🚀 #StartupLife #StartupLessons #Sales #CoffeeIsForClosers 

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Some of the most inspiring founders I've backed take expertise from one field and apply it to another. They're able to create solutions that might not emerge within disciplinary silos. I call these people "missionary misfits.” I'm drawn to these misfits because they tackle big problems without being constrained by the “rules” of individual domains. They combine their deep subject expertise with unbounded curiosity for adjacent disciplines to solve real-world problems. I believe that the most disruptive innovations come from the unconventional remixing of insight and experimentation. That’s why missionary misfits are the apex predators of innovation. These are the ones who initially raise eyebrows yet become study material for future generations. They will transform industries and solve societal problems. And I want to partner with as many as possible.

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If you’re an early-stage founder, finding out what your customers *really* want so you can build the right product is critical. I’m excited to share some of First Round Capital's PMF Method program with Gagan Biyani on Friday! Gagan has founded 3 companies including Udemy, Sprig, and Maven. We’re hosting this live conversation for product leaders & founders on how to reach PMF. You’ll learn: - How to identify your customers' real problems - How to test demand by selling before building - When to write code vs. build a no-code MVP RSVP to join on June 14th (it’s free): https://bit.ly/3VBAK69

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Starting a new fun project with Victor Lee - an AMA series with early stage founders. There are many podcast shows featuring successful, famous entrepreneurs. But what about those who are still relatively early in their journey, perhaps just one step ahead? The zero-to-one founders who have recently cracked the product-market fit and raised Seed or Series A capital. They may not have figured out everything yet, but they have fresh, relatable tips and advice to share. We’ll invite early-stage founders for a one-hour AMA session. Afterwards, we’ll create a public webpage featuring each Q&A session with media clips and transcriptions. This will be 100% free and open to the public. Our first AMA (June 11 1pm PST) will feature Will Drewery, whose company (Diagon) recently raised $5.1 million in Seed funding. We’ll get to know Will better and cover topics such as tips on raising funding in this tough environment. It will be a fun AMA, and you can register for free using the link below. RSVP now!

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I’m fortunate to spend time with a small group of people whom I consider to be the next generation of startup c-level executives. These folks have a lot in common. They’re often in VP level roles, have crazy high ceilings, and they’re perpetually looking to take their game to the next level. They’re running hard. Really hard. Oftentimes, they’re running just as hard at home. In many cases this career apex seems to coincide with having a young family. Sometimes, they run until they crash. I find this comes up a lot in our conversations. I’ve been there. I’ve seen good people leave good companies simply because they’re tired. Longevity is about maintenance. I'm into maintenance. Here are five maintenance strategies that have worked for me; 1/ Align time and priorities. In startups workload exceeds capacity so you need to decide when you work and what you work on. This is a life decision, not a business decision. 2/ Develop a maintenance process to increase longevity. What are you doing daily, weekly and monthly to ensure you’re operating in easy mode? 3/ Understand the power of identity. Exercise caution if what you do is who you are. Startups are volatile and high risk. Detach professional failures from failures of self. 4/ Play the infinite game. Understand that the game you're playing has no finish line. The goal is to keep playing and find joy in the pursuit. 5/ Build a personal board of directors. Startups may be for pirates and romantics, but that doesn’t mean you have to face the world alone. Building a network around you will help commiserate and think through difficult problems. More here, On Longevity: https://lnkd.in/duMCPtSV

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I’m so excited to announce the new name of the vetted community for startup founders I'm building: Village Lane Village Lane connects ambitious early-stage startup founders, both in-person and online, who have at least $100k in ARR or $250k in funding. The name Village Lane is deeply personal to me... It's the street I lived on after business school, in an apartment with my friend Andrew - the kindest, most welcoming, supportive person I’ve ever met, who sadly passed away suddenly a few weeks ago at only 31 years old. It’s also the place where I went full-time on Just Go Grind for the first time when it was a daily podcast and then joined VITALIZE Venture Capital. It was a special time and place and where I took a giant leap in my career. I envision Village Lane (the community) being similar - a special place filled with kind, supportive members looking to take a giant step forward with their businesses. Several experiences have led to the creation of Village Lane: - A transformative MBA experience at USC - Working at VITALIZE Venture Capital for 2.5 years - Growing my social media audience to 40,000+ followers - Building this newsletter to 21,000+ subscribers - Hosting 400+ podcast interviews with founders & investors - Creating an angel investing community with hundreds of members Now I'm focused on helping founders connect, build their personal brand, and create more successful businesses. Village Lane's in-person events will include things like: - Co-working - Social activities - AMAs - Retreats The online component of Village Lane will include: - A member directory - Slack group - Vendor suggestions - Tech stacks - An investor database - Media exposure and amplification - Personal branding assistance We'll also phase in monthly digital peer groups as membership grows. This will all be built around our members and their needs. I’ll share more details as this evolves. Interested in joining? Learn more and apply below.

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"Stay Mobile, My Friends." A great tag at the end of a video, or great advice for life? Probably both, as evidenced by my most recent conversation. The latest episode of Building Value launched yesterday, with an interview with THE Mr. Mobile himself, Michael Fisher. In short: it was excellent, and you'll definitely enjoy it. We talked about a whole range of subjects, including: 🤯 The Importance of Innovation: We discuss the need for creativity in the saturated market of YouTube, and his co-founding of Clicks Technology. 🎭 Our Backgrounds in Theatre: We delve into how our theater skills have helped us in content creation, particularly in aspects like scriptwriting, on-camera confidence, and engaging storytelling. (Hat tip to Cindy Gold and Rives Collins for my own skills!) 🙅‍♂️ Ethical Considerations in Monetization and Transparency with Audiences: We discussed the importance of being upfront about sponsorships and endorsements, and how direct monetization has shifted over the last decade. 🤝 Long-term Trust: Michael describes the work of building real, meaningful relationships with an audience by sticking to ethical content creation practices, reflecting on how this has impacted his and others' growth over time. Want to watch or listen? Here's what you need: 🎥 https://lnkd.in/gV6dh5sV 🎧 https://lnkd.in/gZppM7PW PS. Shout out to Christopher Chapman for the naming scheme of this and future episodes. How did I not think of "The Value of..." as a titling concept? 🤦‍♂️

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CEOs often have a unique vantage point within the company—we get a little taste of every department, and we also have a better vantage point when it comes to seeing how departments interact with one another. From my experience, I've noticed that this can be a bit of a struggle! Each department is so focused on what they have to do and accomplish, that it can lead to less collaboration and communication between these departments. I like the tips that are shared in this piece: 💠 Extend executive alignment practices down to tactical levels. Broader awareness of the health of critical relationships will enable leaders to assess where collaboration is dragging. 💠 Develop employee strategic and interpersonal skills. These skills help teams navigate tricky group dynamics, grasp how different pieces of a project fit together, and speak a common language. 💠 Look for collaboration drag within functions or teams. Functional leaders can start by reducing nice-to-have collaboration in favor of must-have collaboration. What do you think of these tips? And how to do you encourage cross-functional collaboration on your teams? #CrossFunctionalCollaboration #Collaboration #CEO #Advice

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👉 Building up a new podcast is *already* been an enlightening experience. Have had a chance to chat with some amazing folks, got some incredible feedback, and have a ton of ideas for how this series will proceed. I will say, the most exciting part of my recent podcast, "Building Products with Generative AI", is that there is a narrative that is building throughout each episode. I'm not going to reveal what that is just yet, but if you watch each episode, you'll start to notice a solid pattern!

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Over the past year, Silicon Valley’s approach to management has dramatically shifted. Here’s a deeper dive into what’s happening: 🚨 Facebook/Meta, Twitter/X, Google/Alphabet Inc. Too many senior directors and VPs managing instead of building. Zuckerberg’s remark a year ago highlighted this, and now we see Google laying off VPs and Senior Directors who’ve been there for over 20 years. 📉 David O. Sacks “Everyone wants to be a manager,” creating layers of management that dilute productivity. Ambitious individual contributors are promoted to manage teams, often leading to inefficiency and higher costs. Sacks perfectly explains the cascade effect where the star IC becomes a manager, builds a team, and the cycle continues, leading to an overabundance of management layers. Clip from All-In Podcast ft. David O. Sacks & Jason Calacanis https://lnkd.in/gh6H75WV 🗂️ Mark Zuckerberg “I don’t think you want a management structure that’s just managers managing managers managing managers managing managers.” His quote reflects a broader problem of infinite delegation: everyone wants to manage, but few want to do the actual work. 🧑‍💻 Elon Musk When he took over Twitter, he found many engineers hadn’t coded in months due to management bloat. Engineers were told that to be a manager, they shouldn’t code, which led to a significant drop in actual productive work. What’s Changing 🤔 Startups have always thrived on the builder mentality. Now, even the most prominent CEOs in Silicon Valley recognize this issue. They are actively cutting unnecessary management layers and empowering individual contributors again. This shift aims to balance thinkers and doers, ensuring that ambition doesn’t lead to inefficiency. Companies like Meta and Twitter are setting examples. Meta plans to reduce VP positions to foster a leaner and more productive environment. Twitter’s approach under Musk is a clear move towards prioritizing actual work over hierarchical management. Why It Matters 🧐 This shift is about bringing back the builder mentality. It’s crucial to ensure that the best minds are focused on building and creating, not just managing. Ambition should drive innovation, not bureaucracy. In the end, it’s the builders who push boundaries and drive progress.

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Take it from me, there’s no better way to learn excellent and practical ways to overhaul your experimentation efficacy! Erin makes critical thinking fun and highly accessible in this workshop, June 11:

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I remember chatting with Steve Jobs when he would come to our office at IDEO with his most intractable design problems. He was so much more than the co-founder of Apple. He was the man who truly merged technology and design. The man who raised consumer expectations for thoughtfully made products. The man who gave users not what they asked for, but what upon seeing it, is what they wanted all along. His influence still looms large more than a dozen years after his passing. Even the staunchest critics of Apple can’t deny he helped shape the modern design and business world. We often ask: “What does it take to make the next Steve Jobs?” I interviewed dozens of designers, design scholars, entrepreneurs, and CEOs on the role of design in Silicon Valley. My research led me to identify five traits (what I call ‘Jobsian’ traits) that could shape the next great design-tech leader. If you want to be the next great leader in design-tech, this is *all* you need.

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Benchmarks are tricky things in the world of community building. In an industry where we prioritize individual connections, safe spaces, and mutual concern over numbers, benchmarks can feel flat, meaningless, or plain useless to measure our success. But you know what’s worse? Entering into a massive, important, and costly endeavor blindly—with no measures of success. In the past, I’ve shied away from prescribing or sharing benchmarks with community builders. In some ways, I thought it went against my values. How do benchmarks from mission-specific communities provide value to other communities doing totally different stuff? How do I support community managers in following their vision if they’re distracted by measurements that aren’t part of their story? But I field questions daily that could be answered by sharing what my team and I have learned from guiding hundreds of community strategies over the past decade. Questions like: 🧡 How many members should we expect after our first month? And our first year? 🧡 How big should our email list be before we launch? 🧡 What percentage of people should show up to our virtual events? Being the research nerds that we are, my team and I dug into our past work and started to identify patterns of success. Then it hit us … sharing these benchmarks is powerful. The transparency alone is powerful, but we also started to understand that, by sharing these patterns and norms, these benchmarks might actually alleviate anxiety, help community builders tell a compelling story to stakeholders, and create space to focus on the things that matter most! With reliable benchmarks, you can set realistic expectations for your work, which means you can turn away from anxiety—and toward celebration! And that’s a much more sustainable mindset. You have a world-changing impact to make, and if the path to getting there is paved with nothing but second-guessing and struggle, then you will eventually grow too exhausted to continue. That's why, on April 30, we’ll dive into the most crucial benchmarks for leading an effective community. It’ll be our team’s first event on Circle, and I’m excited to try something new with you—and share some truly thrilling news from The CMJ Group! (You’ll need to sign up for our Circle Community to join the workshop, but it’ll be so worth it.) We will explore the common patterns that repeatedly lead to community success. Whether you're just getting started or looking to take an existing community to the next level, learn the essential framework for community success based on real-world examples and data. RSVP HERE: https://lnkd.in/euyv2HiX

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Let's finally get rid off the "VC alphabet song" and redo the system to become more founder friendly. "The benchmarks set by funding stages are often arbitrary and not necessarily aligned with the actual development needs of individual startups." #vc #venturecapital #founder #fundraising #startups #fundingstages #funding #fundingrounds #pitchbook

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Kudos to Zuck for taking aim at VP titles, the proliferation of which is inversely correlated to how lean a company is and how fast it can move. Hope more CEOs follow in his footsteps. It’s also an appropriate time to reshare my old article on Titles. It’s a call to arms to be very thoughtful and intentional about Director / VP titles and avoid them for as long as possible. https://lnkd.in/g4zQkEr

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This is a must listen to for anyone B2B founder. How to figure out Product Market Fit. One of best frameworks I've seen in a while. https://lnkd.in/ghSmhVNB

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Work at a natural pace. In Cal Newport's new book "Slow Productivity" he walks through 3 components to accomplishment without burnout. 1. Do fewer things 2. Work at a natural pace  3. Obsess over quality Working at a natural pace is an area I'm focused on as I transition to whatever is next in my career. Most of my career's natural pace was driven by anxiety, coffee, HIIT workouts and more caffeine - which I'm pretty sure isn't what he means. In my late 40's though, that just doesn't work anymore. Nor do I want it to. It's a tricky philosophy though because if you're in the startup world I don't know how you build something meaningful and work at a natural pace. I've never seen it happen. It appears this is a philosophy that needs to be applied to a specific time and place vs. everyone, everywhere. Anway, I don't have the answers, I'm just exploring different questions. What I do know is working at a natural place seems to be more appropriate for where I am today. 

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🚨 The former CFO of Dropbox, Sujay Jaswa oversees the investment and operating activities as a founding partner at WndrCo, alongside media vet Jeffrey Katzenberg. He joins us for VC Wednesdays.🚨 🖋️  You recently closed a $460 million VC fund. Where are you looking to deploy that? Everything we do is around the idea of the future of work and helping people optimize how they get work done. That’s why we're investors in companies like Airtable, Figma, Databricks, Deel, 1Password and others. That won’t change, but now, you'll see us really focus on the applications of AI that will meaningfully disrupt how work gets done, like in finance, HR and customer support. 🖋️  Why should founders work with WndrCo? One thing that we do that's different is starting one to two companies a year in areas that we think have the potential to yield big returns. So, when we talk to entrepreneurs, our operating experience stays current, and that angle on venture is fairly unique. The second is that each partner at WndrCo has built something, so we have the empathy that comes from that experience. Third, we do only five to seven deals a year, versus bigger firms that do hundreds. Because we have a smaller portfolio, entrepreneurs can get a hold of literally every partner within a couple of hours, 365 days a year. 🖋️ Which startup pitch sticks out the most in your memory over others and why? My favorite is one that’s not a household name yet, even though the business is absolutely on fire. It’s Aura, an all-in-one product to protect you and your family online. The idea is that unlike the physical world, you have no idea what your kids are doing on their phones and devices. Aura gives parents the tools to navigate raising a kid in our mobile-first and digital-first world. When the founder, Hari Ravichandran, walked me through how he would take it to market, it was love at first sight. He's an extraordinary entrepreneur and the best go-to-market person I've ever met when it comes to consumer products. 🖋️ What’s one investment you regret passing on and why? At the end of the day, this whole business is built on being part of monster companies as early as possible. One of the best enterprise companies of the last decade is Databricks. The founder and CEO, Ali Ghodsi, is a very good friend of mine, and for whatever reason, it never occurred to me in the early years to twist his arm to try and let him take our money. We invested in Databricks later than I’d have liked to. 🖋️  What’s the biggest thing you’ve learned working with Jeffrey Katzenberg? The biggest thing I've learned is that you can't be him, and it’s impossible to keep up with him. He's relentless, and I have never met someone who works harder than him. If he says he's going to do something, no matter how hard, if it's within his capabilities, he'll do it. He's a doer, and he just gets stuff done. I admire that so tremendously. #VCWednesdays #vc #venturecapital #startups #TechonLinkedIn

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