Keely Spillane

Last night's Technology Association of Oregon panel discussion on raising capital for AI ventures was full of interesting takeaways. The event brought together leading PNW VCs, CEOs, and funders to share their perspectives and best practices. Here's what you need to know: ➡ The AI/ML space is rapidly evolving, presenting huge opportunities for startups tackling real business problems. VCs are actively seeking out the most ambitious and disruptive companies in this domain. ➡ Having an "unfair advantage" is key - whether that's proprietary data sets, unique domain expertise, or unparalleled access to customers. AI ventures need strong differentiation to stand out. ➡ Build relationships early with VCs, even before you're ready to raise. Their insights and connections can accelerate your journey. The PNW venture ecosystem is highly collaborative and accessible. ➡ Don't be deterred by the perceived lack of local funding. Great companies with compelling visions will get funded, period. Leverage the PNW's strengths in developer/engineering talent. ➡ Recognize and proactively address the potential downsides of AI - from data privacy to model bias. Building responsibly is both an obligation and an opportunity. ➡ Move fast, be bold. Raising capital is always hard, but fortune favors the brave in this space. With the right team, tech and traction, you can build a world-changing business here in the PNW. Thanks to the fantastic panelists Diane Fraiman (Voyager Capital), Geoff Harris (Flying Fish), Jon Maroney (OVF), Chris Sestito (Hidden Layer), Jon Turow (Madrona) for sharing their insights, and to Kristy Edwards for moderating!

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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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Roon's most recent launch, Roon Fertility, is an exciting one. If you're navigating a fertility journey, or are even fertility curious, I encourage you to check it out! It's a labor of love that brings you trusted responses to any question – all through short-form videos and AI instant answers, powered by fertility experts. From the very basics (Should I freeze my eggs? What factors impact male fertility?) to the most specific (Can I do PGT-M to select embryos without the BRCA mutation?). Personally, it's been a dream to work with my childhood idol (and name twin), Olympian Tara Lipinski, to bring this to life. Check out this People article on why she's passionate about Roon: https://lnkd.in/e3BpxgdY & join Roon for free at roon.com

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On the time Y Combinator cofounder Jessica Livingston tore me a new one and changed the future org structure of Ramp: At YC, we attended weekly office hours where every startup shared 1/ their weekly growth %, 2/ their biggest problem, and 3/ what they were doing to solve it. That week in summer 2015 our startup Paribus had grown 20% w/w, our biggest problem was that we were getting too many customer support tickets, and our proposed solution was to hire a customer support person (as the third hire at a then two-person startup). Jessica pointed out that if our solution was to hire someone to deal with customer issues, then next week when we grew more we’d have to hire another person, then another, and so on. Her point was that the real solution isn’t solving tickets, it’s listening to customers and building a better product so customers never need to write in the first place. She told us how Brian Chesky of Airbnb, an icon even then, would still walk around wearing a Jawbone headset so he could personally take support calls, hear customer feedback and deal with problems immediately. She (kindly and graciously) schooled us in front of the group, and it was one of the best learning moments I’ve had as a founder. In a sense, every customer support ticket is a privilege – someone took time out of their day to write about how to improve your product. But it’s also a failure – you could’ve saved them that time by making the product better and more intuitive in the first place. You can’t out-hire a bad product, or compensate for poor taste with a big support team. Support is not a cost to minimize, it’s a key function every company should take seriously. When you listen to customers and make your product intuitive, you get output graphs like the below – where the rate of active user growth far exceeds the rate of support tickets. To this day, almost a decade later, support reports into product at Ramp

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A buddy of mine in adtech sales recently quipped, "If AI takes our jobs, I'll be fine—someone's still got to sell the AI." This was, of course, tongue-in-cheek, but it got my wheels turning about the future for communicators and marketers. Will we be left behind as connections turn into transactions and stories lose their market value? While we wait for AI to become our master, for the time being, we're still selling to humans. And that's precisely why human-centric marketing and communication is more crucial than ever. AI can crunch numbers and automate processes, but it can't replicate authentic human connection or craft narratives that resonate on an emotional level. So, while my buddy jokes about how sales is impervious to the AI apocalypse, he's inadvertently highlighted marketrs and communicators' enduring value. We're the storytellers, the relationship builders, the emotional connectors. Even in a future  world of AI vs. AI, storytelling will remain the ultimate differentiator. For an AI to rise above its peers and claim "overlord" status, it needs more than superior algorithms—it needs a compelling narrative. It needs a story that engages, persuades, and paves the way for its ascendance. And that's where we come in... 🤖 😎 #AI #Marketing #StrategicCommunications #Content

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Had a great conversation with Jacquelyn Miller and Christina Farr on the ins and outs of the direct communication method for startups. They had lots of great advice, which you can check out at the blog. My big takeaway, personally, is that there's truly no substitute for authentic expertise: Founders eat, breathe, and sleep their startup's market, giving them the kind of nuanced, insightful perspective that nobody else can provide. You don't need to be a professional writer or a seasoned on-camera personality to shine; you just have to give your real thoughts on the topic.

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Another year of layoffs/restructuring, "investing in the future," and economic paralysis. I wrote a post about Cannes last year (link in comments) and most of it still rings true. Is Cannes still worth it? 1. Maybe it's my feed, maybe it's a reality, but more and more leaders are concerned about being on a stage (ANY STAGE) this year than ever before. Personal brand engagement seems more important than brand engagement right now. Is it because the tenure of jobs continues to shrink? Do innovation, ageism, sales performance and the speed in which the world is moving right now all play a role? (All things I've been thinking about.) Cannes provides these stages. And yes, almost all are pay-to-play 2. The media landscape continues to change. There are less journalists (anyone who pitches the trades knows this and our friends at Ad Age and ADWEEK are inundated with more "news" than they can currently cover) and more pitches. LinkedIn, Substack and newsletters have become media outlets in their own right - often reaching the masses in a way traditional media with a paywall can't. Will being at Cannes help you break through the media hurdles many agencies are experiencing? 3. We can't ignore the recession that ad/marketing world is experiencing. Every day I hear of another wild pitching experience, projects that go from $500k to $75k in a matter of 2 weeks, and project/pitching purgatory - brands adding weeks to months in their decision making. Will decisions finally be made in Cannes? 4. Experience, community and celebrity still get people excited. And that's what happens at Cannes. People connect. They network. They congregate in one of the most beautiful places in the world see and hear celebrities talk about creativity. It's this one-on-one experience that, in the end, makes Cannes, Cannes. (To me, this is the benefit - I just question the ROI for most.) So, in today's landscape, do I still think Cannes is worth it? I don't know... I feel deeply for so many who are out of work and those smaller indie agencies who are still waiting for their 2024 break. But, I also know that marketers and recruiters look for those who have "award-winning work" as the leaders to take their brand/service/product to the next level. #GoodAdvice should you want it... 𝐃𝐈𝐒𝐑𝐔𝐏𝐓 𝐂𝐀𝐍𝐍𝐄𝐒. You are marketers and creatives. Treat yourself as a client. Highjack this week by making or doing something really fucking cool. I see so much drive, creativity, and innovation in all the talent out there. YOU have the power to get all of those people in Cannes talking. #Cannes #marketing #advertising #creativeagency

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Facebook: An Underappreciated Resource for Tapping into the Young Adult Market. Marketers have gravitated towards platforms like TikTok, X, and LinkedIn, oftentimes relegating Facebook to a platform that doesn't carry as much weight. This perspective may be overlooking significant opportunities. My partner managed to cultivate an audience of two million on Facebook within the last year. This demographic is not only young and affluent, but also primarily female: the exact opposite of Facebook's reputation. If you're aiming to engage younger consumers, consider revisiting platforms that may have been prematurely deemed obsolete. What's your experience been like marketing on Facebook?

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Doesn’t matter if you are building a fintech or lifestyle brand, or anything in between - hiring great journalists is step 1 to nailing the “brand as media company” thing. Robinhood hired Joshua Topolsky to run Sherwood (and then acquired David Crowther’s Chartr) RH hired former Architectural Digest Editor-in-Chief Margaret Russell. Call it what you want - brand publishing, brand journalism, content to commerce - but the brands getting it right understand both the upside (gaining massive trust & authority and reducing customer acquisition cost) and the table stakes (hiring talented reporters + editors). In turn, they're finding sustainable ways to produce content that matters, and audiences rely on to do their jobs/live their lives - while driving the overarching business forward. You don’t need to hire big names or do it on the scale of these behemoths - you just need to hire people with topical expertise and authority, and find your niche. And there are a lot of incredibly talented people out there.

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I know at least 20 former marketing colleagues who have been laid off in the past few months, and it’s tough out there. Victims of layoffs have long suspected that they are viewed as less favorable candidates than their currently employed counterparts, but have had a hard time proving that theory. However, a former colleague of mine who was recently impacted shared a job post with me that confirms that theory is true (in at least some organizations). One of the job requirements (yes, it was a REQUIREMENT!) was that the candidate must have a “consistent working history”. I don’t really know many other ways to interpret that. I won’t get into how wildly discriminatory this requirement is towards the group of people who tend to take on caregiving roles, because that’s a whole post on its own. Recruiters and hiring managers: I urge you to change your perspective. As someone who has been laid off in the past and who knows many people who have been as well, the decision rarely has anything to do with performance and everything to do with numbers; company numbers that are out of said employee’s control. Of all the people I know recently impacted, there is not a single one that I feel lacked talent or could be viewed as “waste”. In fact, some of the most talented people I’ve worked with have been impacted! Instead of viewing these candidates as undesirable (for whatever reason), consider the fact that you now have a market filled with candidates who are hungrier than ever, ready to give their all, and can get started almost immediately. If you are a recruiter currently looking for talented marketers, feel free to share your job listing(s) with my network. If you are currently searching for work, I’d be happy to help in any way I can.

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In addition to producing WTF News (the best show ever), keeping our website beautiful, running email, social, paid, SEO, market research, outbound (the list goes on and on...), Hubilo's marketing team pumps out a ton of content, especially blogs! Here are the blogs we've published JUST this month: ✍ 32 Proven Tips to Boost Webinar Registration and Attendance ✍ How Evergreen Webinars Can Boost Your Sales Funnel: A Complete Guide to Effective On-Demand Content ✍ How to Keep Your Audience Hooked: Essential Tips for Webinar Engagement ✍ Webinar Success Blueprint: Crafting the Perfect Webinar Brief for Marketers ✍ Top 6 Marketing FAQs: How to Promote, Schedule, and Measure your Webinar Success ✍ The Complete Guide to Webinar Reminder Emails (including templates + examples!) ✍ How to Craft an Effective Webinar Email Sequence (with examples) ✍ Using a CRM Integration with Webinar Platforms ✍ Engaging Webinar Audience Techniques for Businesses Read all of these and more here: https://lnkd.in/gEjUde7F Pictured: T. Swift and Post Malone in a tornado of our most recently published content 😉

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I asked media for their PR pet peeves and Alan Henry, PMP from WIRED did not disappoint with the following insights: ☑ "Pitches that are *completely* unrelated to my field, my publication, or even things I've covered in the past. You can very easily find out who I am and what I do with one glance at my LinkedIn profile or any of my social handles. I don't understand why I still get pitches for businesses not remotely in my wheelhouse. And I don't mean 'oh, it's a field in tech that isn't on my beat at WIRED,' I mean this is a pitch for a completely different industry." ☑ "PR reps that go after your accounts without so much as blinking at the boundary they've just crossed. I've had reps who come after my personal email addresses and social handles before attempting to contact me professionally. I know sometimes folks get bad email lists, and that's fine - and usually, if I tell someone to reach out to my professional address, they do. However, there's still something weird about someone reaching out with a highly detailed pitch to your Instagram inbox, where you would never see it." ☑ "Incessant follow-ups! Once, maybe twice, I get it. Usually, I tell my PR friends that I read everything I get (and I do!), but if I don't respond, I'm not interested. If they REALLY need me to reply, say so, and I'll get back to them. But I've had chains of pitches that went on for five or six follow-ups that I only learned went on that long because I muted the conversation after the third or fourth, so I didn't see any more of them. Or worse, email lists that never, EVER let you unsubscribe, even if they claim to unsubscribe you. I tend to look at my spam folder semi-regularly to make sure I don't miss anything important that may have been filtered accidentally, and sometimes I'll see someone on their seventh follow-up and wonder if they're just fulfilling a quota or if they ever truly think they'll hear back from me." ✍ 🚘Media drive-by takes on PR #pr #publicrelations #communications #mediapov

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Getting back into B2B communications can take a minute after spending a few years at a big tech consumer company. Here are some quick tips to help with the transition, especially as people take on new career paths given the times we are in: Get your hands on updated data: Company data should be accessible and understandable for everyone, particularly communications teams, who play a pivotal role in initiating the sales process by building awareness. This data should be updated in real time and be straightforward enough that it doesn't require a PhD to understand a spreadsheet, eliminating the need for downloading or taking screenshots, which can instantly render the data outdated. When Comms teams can easily access fresh sales data, they can align their efforts with sales goals more efficiently. Listen to recorded demos and calls: Recorded calls provide immediate insights into frequent product questions. This helps improve internal FAQs, identify existing product gaps, and prepare for press interviews. Additionally, reviewing these recordings can improve your understanding of how your product compares to competitors and clarify your market advantages. Attend sales planning to listen and learn: Ask to be added to upcoming sales planning meetings as they offer an excellent opportunity for communicators to listen and catch a glimpse of the company's projected direction for the year. This helps Comms professionals design targeted campaigns that support sales initiatives and align with overall business objectives. Schedule a weekly go-to-market (GTM) call: Organize a GTM call with key team contributors for alignment. Include a dedicated update section from sales in these meetings to keep teams informed about the business. 👀 the competition: No brainer - monitor competitors on social media to understand market positioning, products and their strategies. Keep a log every time a competitor says "revolutionizing," "next-gen," or boasts about a LLM tool without explaining how they're ensuring responsible use of customer data. And then make a personal commitment to never do the same, as this kind of positioning harms the industry's credibility. Also, endless eye-rolling is detrimental to your health. #B2B #Comms #PR #sales #startup #career #careeradvice #tips #AI

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Sure, you can use #AI to crank out corporate blog posts at lightning speed. But should you? Without some safeguards, you might find your performance, and even your search rankings, plummet just as quickly as those articles are produced. The amazing Highwire content team (particularly Sarah LeBoeuf and Sam Prell) conducted a controlled experiment in the effectiveness (not just speed) of AI-generated content compared to human writers, and the results are essential reading for anyone in #marketing or #pr looking to use AI wisely. https://lnkd.in/engRHqYf

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One of my favorites, Jordan Birnbaum, unpacking noncontextualized guidance and the pitfalls of "generally accepted wisdom." "The only way in which noncontextual business advice can offer value is if you think like an artist. It may be wise to borrow or, even better, steal. But following noncontextual advice without evaluating your context is like wearing a blindfold on a mountain climb because you got the directions 'up.' Then, what to make of the 'importance of saying 'No'' articles? Be intentional with focus and clear with goals, which for 97 percent of us include career development. Careers are developed by saying 'Yes'; please do not actively avoid things that might broaden your horizons." https://lnkd.in/eJe7gMvk

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Startups shouldn't pay PR firms $15K/month when reporters want to hear from founders directly! I'm nominated to host a talk on PR tactics at TechCrunch Disrupt, but I need your vote to win a slot https://lnkd.in/gYwPXYcW Lesson 1: No one cares about what you're "excited to share". Stop pitching your talking points or product updates and instead focus on what people actually want to read about -- Huge problems to be solved, intriguing data points, inspiring missions, and emotional founder stories. It'd be so fun to get back on the TechCrunch Disrupt stage to teach startups how to boost their recruiting and fundraising with great press coverage, so I'd deeply appreciate your 10-second upvote to score one of the Audience Choice slots. Just log in with Google here and click the green up arrow: https://lnkd.in/gYwPXYcW Thank you!

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Are we helping or hurting? That is a question many residents of San Francisco ask ourselves in the midst of a stark and increasing equity gap. As a parent, community member, and incoming board member of the Horizons at San Francisco Friends School, I’m keenly aware of the potential learning loss our public school students in the Mission District experience in the summer months without our support. Our city is undergoing another crisis - looming budget cuts threaten vital programs like Horizons at SFFS that provide equitable learning for Mission youth. We urgently need your support to secure bridge funding and ensure our summer enrichment continues. Our scholars and families are relying on Horizons' high-quality academics and social-emotional growth.  Horizons has been successfully leveraging the months when students are out of school to stem summer learning loss for children in San Francisco for ~10 years. The program has also intentionally increased impact by supporting their scholars through their educational journey during the school year and into High School. Last year, Horizons impacted 150+ scholars with targeted small classroom instruction, confidence-building, and joyful community enrichment experiences- thanks to our dedicated summer education workforce. But we can't continue without you. Please join me in supporting Horizons at SFFS today to expand partnerships, engage more crisis-impacted families, and grow our supportive community stronger. In past years, the SF Department of Children, Youth and Families has been a partner to increase access to education for our students. This summer, as we face a potential 40% loss to our summer program due to DCYF funding cuts that have impacted so many vital programs in our city, we’ve decided to celebrate Horizons Giving Day, the whole month of May. Please join me in our movement - your gift saves the summer for San Francisco scholars and helps bridge the educational equity gap in our city. Let’s help together. In gratitude, friendship and community, Aneesha #GiveTheGiftofSummer #SparkPassions #HorizonsGivingDay https://lnkd.in/gJAYnibC Links for reference: Horizons at SFFS: https://lnkd.in/gfsdugDX Impact Report: https://lnkd.in/gZc2jn85 Press Release on DCYF Loss of Funding: https://lnkd.in/gNprpSyB

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I recently faced one of those forehead-slapping moments: we received an RFP from a media buying agency (on behalf of their brand client) to run an influencer marketing campaign for an over-the-counter product exclusively on TikTok. Sounds great, right? There’s just one problem—TikTok doesn't allow ads or sponsored content for OTC healthcare-related products. This mix-up brings up a couple of important reminders: 1️⃣ Know the Rules: It's important that marketing agencies of all kinds keep up-to-date with the ever-changing guidelines of social platforms, so they don’t make client promises that can’t be fulfilled. Getting creative with marketing is great, but staying within the lines safeguards client interests and campaign viability. 2️⃣ Choose Your Partners Wisely: Make sure the agencies you partner with are not just creative, but also honest and compliant. The last thing anyone wants is to backtrack or, worse, end up on the wrong side of platform policies. Some agencies might take the risk and run the campaign anyway, hoping it doesn’t get flagged. But experience has taught us that while pushing the envelope is a good thing, it should always be done within the boundaries of the platform rules. This ensures our clients' campaigns are successful and impactful — without resorting to questionable tactics or risking public trust.

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I've been hard on venture capital. Even if it may not feel like it, there are responsible, kind, smart, and helpful people in the VC world. You just have to dig, so I'd like to make a positive post today highlighting firms/ studios/ individuals who have been nothing but great to me. My disdain has been aimed in the direction of larger VCs who appear untouchable, but these are examples of people doing positive things that I would recommend anyone connect with: Rule 1 Ventures - Todd Ehrlich and team took me on at a volatile time in my life with my first startup. He gave me a job as an Entrepreneur in Residence, and to this day he still offers guidance when at times I was difficult to work with. I was young, hungry, and I thought I could will anything into existence. But I failed in being able to step back and see the bigger picture of how much value this firm could offer me long-term. I hope I left Rule 1 in a better place than when I started, even if I wasn't always the most tactful person in my approach. I'm truly grateful Todd still supports me and sees something in me. Atlanta Ventures - A.T. Gimbel is a salt of the earth human who was the first person to make me believe I could make something of myself in tech. They even offered me a job at one of their portfolio companies when I was "floating in the wind" a bit. Our vision for my first company didn't align with the scale that Atlanta Ventures was looking for, but that never stopped A.T. from offering feedback and supporting us in trying to build our lifestyle business. Chisos Capital - Will Stringer invested in me as a person when I was still feeling like I was in a volatile state trying to figure out this whole startup thing. I still owe him both gratitude and the reaching of my full potential. Pioneer Square Labs - T. A. McCann and I didn't have many conversations, but boy the conversations we did have were valuable. He has so much knowledge to share and a refreshing perspective on life. I would recommend anyone work with Pioneer Square Labs. Mark II - I just recently met Christopher Hand, but he was willing to go out of his way to meet with me and discuss the venture landscape in Alabama. We also got to nerd out about AI and LLMs. He is someone I would no doubt trust to approach AI responsibly. I even got to beta test one of their products, and I would recommend them to anyone. I'm hopeful our paths will cross again in the future. Being edgy/ trying to point out bits of madness in the tech world comes with pros and cons. I don't want to lean into negativity too much, which admittedly I may have previously done. So this is all about positivity. But I'm not done. I'm tagging and talking about more individuals who positively impacted me in the comments below ⬇ Brevity isn't my strongest trait, but this post isn't about reach or impressions...just gratitude. #venturecapital #venturestudio #fundraising #vc

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