Naveen Gupta

Perfecting your product and GTM strategy are surely important. But Box CEO and co-founder Aaron Levie argues there's one factor that outweighs all others in startup success: recognizing and capitalizing on tech and macro tailwinds. Fighting against them? You're setting yourself up for failure. Our full conversation here: https://lnkd.in/gEAPFR-A

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As we explore a seed round of VC funding for Avnir, a mentor has driven into me to "interview them as much as they'll do their due diligence on you!" When I consider professional etiquette important to me (and probably every serious founder), I am reminded of what I've coached hundreds of executives on over the past two decades: "Your culture is a culmination of behaviors you're willing to tolerate!" So, here is a Top 10 List of Professional Etiquette crucial to long-term strategic relationships between VCs and founders: 1️⃣ Respect for Time—Punctuality, Efficient Communication, and Timely Feedforward are demonstrated and genuinely felt. We would both rather me invest time in building the business. 2️⃣ Transparency—Clear Expectations, Honest Feedforward, and Disclosures on conflicts of interest or resource limitations save everyone unnecessarily wasted cycles! 3️⃣ Professionalism—Politeness, Confidentiality, and Objective Evaluation allow courteous interactions, respect for proprietary information, and avoiding bias in evaluating the founder's meritocracy. 4️⃣ Empathy—Understanding the Journey and Constructive Dialogue acknowledge the uphill battle founders face while avoiding unnecessary criticism and providing supportive guidance, demonstrating a genuine interest in their vision. 5️⃣ Integrity—Fair Terms, Follow Through, and Avoiding Overpromising honor commitments during discussions, and create realistic expectations from the relationship. 6️⃣ Co-Creation—Value-adding Mindset and Team Player Attitude accelerate the founder's ability to gain traction and position the VC relationship as transformational vs. simply transactional. 7️⃣ Humility—Avoiding Arrogance, Condescension, and Open-Mindedness acknowledges that both parties have unique expertise to add and enhance the receptivity to unconventional ideas, approaches, and perspectives. 8️⃣ Listening Louder—Present, Engaged, and Clarity of Intent eliminates distractions, brings out what's not being said, and jointly crafts better questions to help uncover the unknown and the undiscovered. 9️⃣ Encouraging—Supportive Communication, Positive Reinforcement, and Inspiration help celebrate small wins and key milestone achievements. It's ideal to light a fire within the relationship rather than under anyone, which seldom lasts! 🔟 Playing the Long Game—Relationship Nurturing and Post-Investment Care establishes the runway for a lasting partnership rather than simply pitching a deck and closing a deal. After the investment decision, sustaining the relationship will determine the partnership's long-term perspective. Jason M. Lemkin, Peter Bell, Cassie Young, and Ed Sim - you exemplify world-class in the relationships you build with your founders. Did I miss anything? #VCFounderRelationship #AlignedExpectations #RelationshipsMatterMoreThanEver

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🔑 The Power of a Written Exercise in Interviewing Revenue Leaders 📝 Hiring the right revenue leader can make or break an organization. As we search for smart folks to drive our revenue growth at Vanta, one approach has consistently proven to be a game-changer: the written exercise. 🔍 Why a Written Exercise? Clarity of Thought: A well designed exercise reveals a candidate's ability to articulate complex ideas clearly and concisely. This skill is vital for revenue leaders who must communicate strategies across diverse teams and stakeholders. Strategic Insight: Through real-world scenarios, candidates demonstrate their strategic thinking and problem-solving abilities. This helps us gauge their approach to challenges and opportunities unique to our business. Analytical Prowess: Written exercises allow candidates to showcase their analytical skills. By dissecting data and presenting actionable insights, we can see how they drive decisions that lead to growth. Cultural Fit: How a candidate approaches a written task can also give us a glimpse into their work ethic, attention to detail, and alignment with our company values and culture. Elliot Goldwater has really nailed this practice, and it's incredible how much the exercise can swing a process towards or away from a candidate. 👥 Have you implemented written exercises in your hiring process? What has been your experience? #RevenueGrowth #Leadership #HiringTrends #Interviewing #TalentAcquisition #Strategy

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During yesterday's LibreQoS APNIC webinar, I posed the question: won't more bandwidth solve these problems? As Herbert Wolverson said, yes, more bandwidth is good, but, still these problems remain if queueing is done incorrectly. Here's my take on why bandwidth alone is not as good as bandwidth + good queueing policies: Generally it was believed that 'data is important, so don't throw it away; hang on to it and send it later'. In practice, this has proven to be suboptimal as two issues may emerge: 1) latency increases for some flows due to heavy demand from other flows using the same bottleneck link, 2) even a single flow can have excessive latency due to aspects of typical TCP behavior (referred to bufferbloat) when the buffers grew large enough that the data being buffered was retransmitted anyway. It turns out that not all data is equally important. Active Queue Management is the art of deciding priorities, both in deciding what data to throw away, but also in allowing some later arriving data to be transmitted ahead of data in another connection that arrived before it. These problems have been studied, and good solutions have been found by using certain queueing policies in routers and switches, referred to as “fq_codel’ and “cake”. These track the different flows not by classifying the data, but by watching the behavior. Flows that send relatively little data (DNS lookups), or at a measured pace (video chat) have priority over flows that send a lot of data as quickly as possible (App and System updates, Video and ISO downloads).

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In vertical SaaS, the very best companies landed with a product solving a specific, burning pain point that horizontal solutions solved badly and then became broad product suites over time (ServiceTitan, Veeva Systems, Doximity, etc). My partner Gordon Ritter calls this “layering the cake”. In vertical AI, the landing wedges are much more brittle. While the painpoints they solve are very real (and often unaddressable by SaaS alone), they’re also much more likely to commodotize in the near term as the tech advances. 👀 Therefore, the need to layer the cake in vertical AI is much more urgent than in vertical SaaS. 👀 The best vertical AI CEOs not only recognize the dynamic, but talk about it openly. Helps those around them keep up the speed of innovation and their eyes on the bigger prize.

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The acquisition game is very different from 10 years ago now that 70% of SaaS acquisitions are led by private equity investors or PE-owned strategic buyers. Most SaaS founders aren't thinking about the new realities of eventually selling their SaaS companies. It's very different than the old days of "sell it for big multiples to a strategic buyer, cash out, and see ya later." Here are 5 questions for founders to consider the new realities of a potential PE-backed exit: 1) Is my company built to keep growing efficiently after I sell it? - Your SaaS metrics need to be healthy. Growing steadily with efficient CAC and solid revenue retention - You need a business that runs without you, the founder. - And you will still be responsible for fixing the problems in your business. 2) Would I invest in the new company with my hard-earned equity or cash? PE buyers don't cash you out of 100% of your equity, just a partial "first bite of the apple" prize. They buy a minority or majority of your company, so you become the major private investor in the acquiring business. This is not an earn-out. You now own shares in a new company that you don't control. You must be confident enough in the new owners, operators, culture, and vision to invest 20-60% of your hard-earned equity in this new venture. 2) Why will this acquisition work to build and sell a much bigger company? Most old-style mergers and acquisitions didn't work for either side. In this new world, founders need to find the right owner/partner with the right strategy and team to ensure their hard-earned equity pays off on their "2nd bite of the apple" when it is sold again. Founders should also do deep due diligence on their acquiring PE investors, not just pitch themselves for "sale" to any takers. 3) Do I trust the new owners and operators to do the right things? Most founders don't stay on as CEOs when they sell to PE buyers. Someone else owns your business (PEs), and they have CEOs who will run the business their way. 90% of founder-CEOs who sell to PE end up as board members with the ability to make suggestions to the new leaders. That's it. You must trust the people and their approach to your business and your precious equity. 4) How will things change now that I'm not the CEO? Maybe you continue running the business as a CEO with new owners for a while, but eventually, you won't be there. Now what? How do you spend your time now that you're only an involved board member? This is very jarring for most former CEOs, so it's worth considering before selling. 5) How will things change now that I have money? The biggest reason to sell a major part of your healthy SaaS business is to take some chips off the table and win a major cash prize. You invested 5-15 years in this business and probably some of your own cash. Now what? Will your life change a little or a lot? It's a whole new world for successful SaaS founders when they sell to PE buyers. #practicalfounders

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At Forum we look at thousands of deals each year across our Accelerator and Pre-Seed funds but only end up investing in a little over 1% of those startups.  As an early stage VC, I am in the business of saying no to nearly every startup I meet, and while there is nuanced rationale for many of the startups I pass on, a vast majority of businesses that don’t meet the qualification to get funded typically fall into one of two buckets. ▪ First time founders have a tendency to go out to market too early to raise pre-seed capital ▪   I’m sure most founders have heard some iteration of this from VCs that ultimately pass on their business.  In some cases it's a blanket excuse covering up for other pass reasons- perhaps a VC doesn’t believe in a team or isn’t bullish on the market opportunity - but in many cases founders simply haven't proven enough to the market to warrant an investment. I meet many teams with an articulate vision for the product that they want to build, but they either haven't performed enough customer discovery to prove demand for their initial wedge product, or need to raise pre-seed capital to build out an MVP.  In those cases, pre-seed investors are unwilling to underwrite those risks.  To be default fundable, teams need to be able to keep costs low, perform extensive customer discovery, and ship some version of an early product - pilots and early paid customers are key. A huge piece of this is having founding engineering talent on the team. ▪Not every startup is a venture opportunity ▪ By definition, a venture backed business is solving a problem within a market opportunity so massive and so desperately needed, that its growth rate is off the charts.   It spreads like a weed, absorbing almost unlimited amounts of capital to fulfill demand within its customer base.   Each year there are maybe 20 companies launched that ultimately have venture scale outcomes. The bar to reach this rarified air is unfathomably high and the reality is the vast majority of founders simply aren’t building for opportunities that have the potential to be one of these generational companies. Many startup founders view VC as the only viable option for capitalizing their business, but not every great business is a venture business, and most successful founders never take VC dollars.  In order to reach an IPO/acquisition large enough to generate venture returns, a startup needs a credible path to $100s of millions in revenue. This is the standard by which early stage opportunities are evaluated. The flip side to this, and I share this feedback often with founders I meet that are building interesting business in non venture markets, if you are able to scale to $10- $20M in revenue that can be a massively successful outcome for a founder.  There are investors who focus on these type outcomes, namely lower middle market PE shops, and the typical path to those deals is a bootstrapped business or a friends/family capital raise.

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Instacart is a market leader when it comes to leveraging AI tools to boost productivity at work. I had an amazing conversation with JJ Zhuang, Instacart’s Chief Architect, who has shepherded over 50 AI-driven initiatives to market across the org. We explored what catapulted Instacart to the forefront of AI integration, supporting radically diverse use cases across various functional areas. One striking insight (echoed by Ethan Mollick and others elsewhere) is that you often don't need specialized tools for specialized work. Frontier models like GPT-4 can seamlessly adapt to a wide range of functions and use cases. They're not just for engineers; they're incredibly versatile tools used by marketing, comms, and legal teams. From generating code to proofreading and ideation, GPT-4 empowers every department to leverage AI for enhanced productivity and innovation. By integrating LLM’s like GPT-4 into their workflows, teams can streamline processes, automate repetitive tasks, and unlock bandwidth for new creative possibilities. How can you harness the power of AI in your own work to boost productivity? Share your thoughts below 👇 Want to hear more insights from JJ? Check out the full podcast episode by clicking the link in the comments.

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ex Google CEO Eric Schmidt spoke at Stanford this week. Lots of nuggets here, but most interesting for the near term, Schmidt believes in the next year AI is set to make a big leap forward. He predicts AI will combine three important features: 1. Vast knowledge retention (1 million token models) 2. Text-to-action capability 3. Personal AI agent fleets While the full impact is unknown, everyone may soon command their own AI teams. Here's an example: Imagine you're developing new quantum computing algorithms. Your AI assistants could: - Continuously scan and synthesize global quantum research papers - Generate novel algorithm ideas based on this knowledge - Simulate and test these algorithms across various quantum architectures - Automatically document findings and prepare draft papers - Identify potential collaborators and draft outreach emails All initiated by a command like "Advance our quantum algorithm research." This could dramatically accelerate R&D cycles and scientific breakthroughs.. https://lnkd.in/eJbg6cnD #frontiertech #AI #futurefrontier

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As we stand on the brink of 2025, the world's technology, infrastructure, AI, Data, Cloud, Crypto, venture and everything else in tech are poised for a transformative year. I am excited to share my predictions for 2025 — insights that I believe will guide us through the next wave of innovations as important as the internet and smartphones. Together, let’s explore the trends that will not only guide and influence our thinking and investment strategies but also inspire us to create a better world through entrepreneurship. Here are a few predictions 💡💡💡: -  Imagine the creation of HealthGPT, BioGPT, NuclearGPT, LogisticsGPT, GovGPT and more - Establishment of a US Bitcoin Reserve by the end of 2025 - SpaceX, OpenAI, Stripe, SHEIN, Databricks, Canvas, Chime, Anduril, and Scale AI are anticipated to go public - 50% of the Department of Government Efficiency (DOGE) new hires are from Silicon Valley. #prediction #2025 #venture #funding #M&A #DOGE #bitcoin #AI #GPT #IPOs #exits #startups #venturecapital #USmarket #databricks #chime #anduril #scaleAI #OpenAI #stripe #spaceX #bytedance #canvas Read more on my Substack  👉 👉 👉

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Here are 7 takeaways from the 2024 SaaS Benchmark Report by High Alpha, Openview, Paddle, and Tremont: 1. Revenue Growth & NRR at public SaaS cos have stabilized 2. 76% of founders are most concerned about GTM Execution 3. Revenue growth is down for companies >1M in ARR 4. Early signs of re-acceleration of revenue growth in early stage cos 5. NRR is a key revenue growth driver for larger companies 6. Companies with higher ACVs has stronger growth & retention rates 7. SaaS Spend bounced back in 2024 What's the most surprising find you had? Comment 👇 #SaaS #GTM

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My predictions for what 2025 will look like for the world of startups 1/ Funding toward legacy vertical SaaS businesses will hit an all time high in 2025. 2/ Flight to SF: SF will be the place as a preseed & seed founder to raise their first rounds. The emerging founders will pop in in SF first before making their ways to NYC and beyond. 3/ Year of Exits: We'll see a lot of the companies that couldn't exit in 2022-2024 start to exit this year through IPO, M&A and more. Will add much liquidity towards the VC market and drive LP diversification versus in 2024 where $35B of the $72B raised towards VC firms went to the top 9 venture funds in the world. 4/ Early stage fintech makes a comeback: The peak for early stage fintech was 2022 with $4.1B raised across 970 deals. 2024 early stage fintech numbers fell to 5 year lows with only $1.9B raised across 505 angel, preseed and seed deals. Seeing some improvements in funding numbers from quarter lowers which was Q2 2024 and some improvement in Q4 2024. Macro trends, AI, and some late stage funding for later fintech cos gives me an impression early stage fintech will rebound next year. 5/ RTO is coming back: The best startups will no longer be distributed but will return to the office in 2025. We'll see an increasing amount of startups, especially the early stage ones, emphasize in person work and hires. 6/ Biohacking the supermarket: Interest in health and longevity for consumers and the advancement of AI are long to lead to more demand for personalized food plans built for each individual person. 7/ Built for you: media and everything we consume on the internet will become for you. Think an extension of the for you page on Tik Tok but for everything else you consume, shop and watch. It won't be long until media becomes personalized to you and I and your favorite influencer is actually AI. 8/ Digital Twin Simulations: Someone will build out your digital AI twin for decision making. From testing career changes to planning relationships, these virtual replicas could provide insights into life’s "what-ifs. 9/ AI buyers: Just like with the rise in SDRs, we'll soon see a company test our buying with AI. Take product features, demos, pricing and more into account and AI will optimize to buy the right vendor stack for a founder based on exactly what they need.

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In the last month, we've all heard this Service-as-a-Software narrative that AI will enable applications to sell an outcome or a full task, rather than a seat as in vertical SaaS. This could then increase annual contract values from 3 or 4-figures to 6 or 7-figures. After all, that is the cost of labor previously delivering the service, right? Service-as-a-Software expands the $650B Software Market into the $10T Services markets. We've heard this seductive VC narrative from Mamoon Hamid at Kleiner Perkins; Sarah Tavel at Benchmark and Pat Grady at Sequoia Capital. Smart investors, no doubt. But what if this thinking ignores the competitive element? Since when is pricing a function of the work you replace, rather than the next application who is seeking to replace you? I suspect customers will see massive savings in cost / task, but competition will render value capture difficult for these first movers. With dozens of AI SDRs, AI Coding Agents, and AI Work Assistants and discerning IT procurement departments, how will these price assumptions sustain? The answer, I think, lies in dusting off Hamilton Helmer's 7 Powers, specifically 3 of them: 1) Network Effects (on users or data) 2) High Switching Costs (system of record) 3) Counter-Positioning (inimitable pricing or delivery mechanism) This is what we are looking for at Optimist Ventures. Would love others' thoughts on this.

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Big announcement below! 👇 Let's talk about the current state of GP-LP affairs: 🤯Emerging VC managers have absolutely exploded over the past 5 years. 📈 At the same time, more and more data has surfaced that shows that emerging VC firms tend to outperform larger, established firms. 🤔 All of this has made it intriguing but tough for LPs to know where to direct their attention. 🛍 GPs frequently meet LPs at conferences who are window shopping but not committed to the asset class or emerging managers. 🧾 And both crews get overwhelmed by transactional convos. So Sydney Paige Thomas and I created Abundance. Abundance is a private, nomination-based retreat for active LPs and top emerging GPs to form new experiences together and build lasting relationships. Why Abundance? Abundance is knowing that there is more than enough for more than one to succeed. And a single win within a community is a win for the community itself. The journey of an emerging VC manager from 1st close to final close or Fund 1 to Fund 2 is (1) communal and (2) requires an abundant mindset. LPs look for structure and confidence to feel comfortable investing in early VC firms. Yet many of the feeds we scroll and conferences we attend reinforce inherent power dynamics and transactional thinking, which allows scarcity mindset to creep in for emerging GPs. Some of the best events I’ve attended have been intentionally non-transactional, e.g. Camp Hustle, Recast Summit, and other GPs’ AGMs. The fundraising success stories we see usually involve a community (usually of other GPs & LPs) coming together to support and open doors for the emerging GP. We designed Abundance to be an immersive gathering that fosters these connections. Starting tonight, ~100 GPs and LPs are descending upon Seattle for the inaugural Abundance retreat. This has been under wraps for months and I can’t wait to see it come to life! Thanks in advance to our awesome sponsors who were the earliest believers in this vision: Sydecar, Amazon Web Services (AWS), Gunderson Dettmer, & Zelda Ventures. And shoutout to my dad Ed Illig for logo design & Halle Kaplan-Allen being the first sponsor to say yes 🤩 Presented by The Council Capital & Symphonic Capital.

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In the Software-as-a-Service (SaaS) industry, retention has become the new top-line metric because of several factors that drive sustainable growth, profitability, and long-term success. Here’s why: 1. Cost of Acquisition vs. Retention Acquiring new customers is expensive: The cost of acquiring new customers (CAC) has increased dramatically due to market saturation and competition. It can take months or even years for new customers to become profitable, making retention critical for maximizing the return on investment (ROI). Retention is more cost-effective: Keeping existing customers happy and ensuring they continue to renew their subscriptions is far more cost-effective than constantly seeking out new customers. Retained customers also have a higher lifetime value (LTV). 2. Predictable Revenue through Renewals Revenue predictability: Recurring revenue from existing customers (renewals and upsells) is more predictable than revenue from new sales. High retention rates provide stability, reduce churn, and lead to more consistent growth. Investors prefer predictable revenue: SaaS companies that demonstrate strong retention rates are seen as less risky and more attractive to investors, as their future cash flows and revenues are more predictable. 3. Expansion Revenue Opportunities Upselling and cross-selling: Retained customers are more likely to engage with additional features, products, or services that the company offers. This leads to expansion revenue, which can significantly contribute to overall growth without the cost of acquiring new customers. Product adoption and engagement: Customers that stick around for longer periods tend to adopt more features and integrate the software deeper into their workflows, which creates a stickiness that further increases retention and expansion opportunities. 4. Customer Advocacy and Brand Loyalty Word-of-mouth and referrals: Happy, long-term customers are more likely to become advocates for the brand, leading to organic referrals and network effects. This not only reduces the need for heavy marketing spend but also brings in high-quality leads who are more likely to convert and stay. Building trust and loyalty: Consistent value delivery over time builds trust and creates brand loyalty, which is critical in a competitive SaaS market where switching costs can be relatively low for customers. 5.Churn’s Negative Impact Churn is costly: Even a slight increase in churn rates can drastically impact revenue growth, especially for SaaS companies with subscription models. A high churn rate means that new sales are simply replacing lost revenue rather than contributing to growth. Poor retention often signals issues with the product, service, or customer support. In summary, focusing on customer retention in SaaS companies not only ensures a steady stream of revenue but also reduces acquisition costs, creates opportunities for upsells, builds loyalty, and provides a competitive edge in saturated markets.

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I am always amazed when someone discovers whitespace in B2B SaaS that is eligible for pre-seed funding. It's interesting to see that Chiratae Ventures led Pre-Seed round for Pepsales. Pepsales is trying to help B2B SaaS companies improve their sales by creating personalized product demos using AI and ML. The pain point they are trying to address is that most demos don't impress buyers because they tend to be generic and one-size-fits-all. Congrats Ajay Singh and Abhinandan Sahgal! Source: INC42, Entrackr, VCCircle #VentureCapital #B2BSaas

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PE - How to Use AI to Unlock Growth in Portfolio Companies All PE firms and portfolio companies should be thinking about unlocking GTM and growth via AI (i.e. not merely ChatGPT or other LLMs but actually implementing apps that are "AI Agents"). 1. What are "AI Agents"? - AI agents are autonomous systems powered by ML and natural language processing, designed to perform tasks with minimal human intervention - They can interpret data, determine the workflow & direction (i.e. make decisions), and execute actions across various functions, continuously improving through self-learning 2. Examples of using AI Agents in PE portfolio companies: - For Sales: AI agents handle lead qualification, respond to inquiries, book meetings, and provide personalized product recommendations, ensuring no opportunities are missed - For Marketing: Generate campaign briefs, segment audiences, create tailored content, and analyze performance to optimize outreach efforts - For Customer Success & Support: Provide 24/7 support, resolve customer issues autonomously, escalate complex cases to human agents with full context, and ensure consistent, brand-aligned responses 3. How PE portfolio companies benefit: - Efficiency: Automate repetitive tasks, enabling teams to focus on high-value activities - Scalability: Handle growing customer volumes without increasing headcount - Personalization: Deliver tailored experiences using real-time data insights - $ Cost Savings: Reduce operational costs by streamlining workflows 4. Business Impact for PE Portfolio Companies: - Accelerate GTM Execution: Faster lead conversion, better customer retention, and enhanced marketing ROI - Improve Metrics: Boost Customer NPS, CSAT, and efficiency - Enable Growth: Scale operations seamlessly while improving team productivity. 5. How PE Firms Must Think About Adoption - Define clear portfolio objectives to use AI agents (not just LLMs) - Ensure integration with existing CRM and data systems - Prioritize high-quality data and ongoing performance monitoring - Use AI agents to complement existing GTM teams, focusing them on automation ------------------ #pe #privateequity #investing #ai

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AI in Vertical SaaS ____ I've been learning from SaaStr content for over a decade now. I loved Jason M. Lemkin's recent interview with Mangomint's Founder / CEO, Daniel Lang, about the growth of vertical SaaS. The entire video resonated with my own vertical SaaS founder experience at CampusLogic as well as the high-growth vertical SaaS companies I have invested in at PHX Ventures (e.g., Virtuous, equipifi, Nurture Boss, Soraban, eVisit, Rivia Health, Botco.ai, Coursedog, etc.). This clip below captures why I am bullish on AI in a vertical SaaS context. I believe the next decade will be the biggest period of productivity gains in my lifetime in most industries. It's a great time to be building an AI-driven vertical SaaS company. ___ PS - I hope everyone has a great week at SaaStr Annual 2024. #b2b #saas #founders

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