Nick Mehta's Recent LinkedIn Posts

In the last 6 weeks, as I've started to think about what I want to do next work-wise, I've had the pleasure of meeting so many people in the early-stage AI world - 44 VCs and 23 founders, to be specific. After you cut through the pessimistic headlines and handwringing about a bubble, I'm struck by the fact that people are trying to solve so many important problems for humans (across work, home, health, education, security, etc.) that previously seemed intractable. It's easy to get cynical on X, but there are a ton of optimists out there. And I appreciate that.

Let's talk about building a VC-backed board. I was incredibly lucky with my board at Gainsight. 6 years after our exit to Vista, I'm still close to every one of my former board members. They were there for me during the great times. And they had our backs during the rough periods. Since I've heard so many founders share nightmare stories about their boards, I wanted to reflect on what we learned along our journey: 1. Prioritize Board Composition. I was lucky to have board members with different skills — financial, GTM, product, etc. And also a balance of communication styles. I remember one legendary board member telling me, "I don't need to be the one speaking up in the meeting; you have a great board; we can just chat 1-1." 2. Prioritize Board Composure. Board members are humans. They have emotions. I find the most effective board members for the companies I work with are ones who don't get too high when things are good and don't get too low when things are bad. As an example, in our fourth quarter of selling, we had a plan of $600K in new ACV. With 1 day to go in the quarter, I told our board we would do… $300K! I'll never forget one of my board members' reaction: "I don't care if you do $300K or $600K. The question is can you do $10M quarters in the future?" [spoiler: we did!] 3. Onboard Board Members on Values. From the beginning, our 5 values at Gainsight were the core of what drove our company. We worked hard to explain our values to Board Members and spoke about them in every board meeting (they were in every deck). As a result, our board always supported us with our teammates. As an example, when we were acquired by Vista, we had to decide what to do with our unvested options. Our board kindly agreed to accelerate the vast majority of these shares. 4. Clarify What I Want. Early on, I created a practice where I identified what I wanted from the board. For each topic, I indicated in closed session beforehand if I wanted it to be (1) just FYI, (2) a feedback session, or (3) approval needed. And I'd indicate if I wanted the board to push my leadership team or praise them. 5. Build Connection. As I mentioned, I'm lucky to be close with all of my board members so many years later. When I had recent tragedy in my life, every one of them called, met me, etc. This came through years of team building. At board dinners, we'd always have a private room, have one conversation, and open with an icebreaker aligned to our values - e.g., "What's the last time in your life that you felt the joy like a little kid?" Below is a "bring your jersey" Board Meeting in 2020 where 2 of my Board Members who are fans of other teams rocked the Black and Gold of my Steelers! I'm grateful to call Roger Lee Ajay Agarwal Byron Deeter Nakul Mandan Sue Barsamian Kirsten Maas Helvey Jeff Lieberman (and my post-VC board members at Vista, John Stalder Nick Prickel Nick Murley Thomas Hogan Eric Roza Sunny Gupta et al too!) friends to this day.

One of the worst times at Gainsight ended up creating one of the best times: In 2017, we had gone from "hot" to "not" (H/T to my friend James Hong!) Our early days were on the path for fast growth at the time: 2013: $1M ARR 2014: $5M (5X) 2015: $16M (~3X) 2016: $30M (~2X) In AI times, that ramp happens in a month, but that was solid traction for that era. The problem was we were TAM constrained (primarily selling to tech companies). So our new logo bookings flattened out and in 2017, we ended at $48M. Deceleration was upon us. Morale dropped. Our head of sales (who was a great person) resigned. A lot of his hired in people did too. I did the usual CEO thing and said "MORE LEADS!" to my CMO Anthony Kennada, but if you are out of TAM, you are out of leads. And we were burning money like we were still in hypergrowth land. So we needed cash. We went out to raise our next round. Our pitch was basically "yes we decelerated... but give us more money and ... profit!" OK it was more artful than that, but not much. We had some ideas of new things we could do, but no evidence to support the ideas. We called all of the VCs who for years had been "huge fans" and said "we'd love to be in business with Gainsight." My guess is we pitched 50 firms. And we got 50 NOs. Worse still, these weren't the early stage nos where people sometimes pass because they don't know who you are. These investors passed knowing exactly who we were! It was a brutal time as a leader. I had to get in front of the company and bring us together, while I had almost no confidence internally. Then something lucky happened. Because we couldn't raise equity capital, we instead raised a small amount of debt. And since we had debt, we needed to get to breakeven pronto. Our retention was good, so all we needed to do was keep growing modestly and not hire anyone. I became a nightmare to every leader and manager at Gainsight. No new hires. No backfills. End of story. Not a good way to run a company long-term (lots of problems come from this approach). But in a year and a half, we were within spitting distance of breakeven. And because we had that profile, we were in the zone for Private Equity firms at the time (near-breakeven, good but not hypergrowth, good retention). That eventually led to Vista Equity Partners buying the company at the end of 2020 for $1.1B. Our last venture round was ~$500M and most were way below that, so everyone was happy. Strangely, in the multiverse, Many Worlds, Sliding Doors alternate reality, we raised that last round (ironically it would have been our Series "F"!) at a $1B+ valuation, we didn't get disciplined, we later had to do massive cuts, and we were probably a zombie company with no exit. Now would it have been better still to have had hypergrowth, gone public and be worth $100B or whatever? Sure. But for me, the story shows that sometimes failures beget successes.

Biggest mistake I've seen in company culture: being generic. At Gainsight, we were pretty well known for our quirky culture. And that was why it worked. I've watched so many founders define their company culture based on what other hot companies (SpaceX, Palantir, Stripe, etc.) have. I'm sure some asked ChatGPT to do it for them... Here's an alternate recipe: * Why: To me, the best cultures start with a founder defining why the culture is personally important to them. Cultures are intimately tied in the early days to the people who created them. Why did you want to create a company? For me, this showed up in the idea that I always wanted to be in an environment where people treated each other as humans above anything else. This turned into our mission statement "human-first business." * Who: Who are the early people that you think represent what's unique about your company? What drives them? What do they value? Who didn't succeed and what was different about them? This might help you capture the essence. As an example, one of our early teammates, Dan Steinman, was always there for others with no expectation of anything in return. * What: What words capture the essence of your cultural vision in a way that they would make no sense in any other company? What terms are so special and unique to what you do? The weirder the better. Our values - including "Childlike Joy" (bring the kid in you to work every day) and "Stay Thirsty, My Friends" (find your inner drive - also clearly a copyright violation off of the Dos Equis commercial!) were strange selections that only fit Gainsight. * When: My personal opinion is canonizing these should be done early, but not too early. We captured most of this 1-3 years in. You need enough reps of hiring people that you have some patterns. Repeat founders might have more of a sense in the beginning, though. * How: For our final 2 of 5 values, we brought our tiny team together and had folks brainstorm words to capture the spirit of our culture. I ultimately made the calls (including overruling on one item), but sometimes the ideas help. Ben Horowitz said it well - "Culture is not a set of beliefs. It's a set of actions." Generic beliefs are the enemy of a culture of action.

A number of the most compelling founders/CEOs I've met invested time understanding themselves so they can do their best work. Indeed, I was talking to a founder recently who said the breakthrough in his business came when he figured out what parts of the job gave him energy versus took away energy. For the latter, he was involved but was able to hire complementary teammates. This gave him a renewed sense of drive. For me, the tool that helped me figure this our was Enneagram. And I was skeptical as hell at first. I got Enneagram-pilled at one of the first meetings for the CEO group I joined in 2009 (YPO). People kept using the term and it sounded straight out of a cult playbook. Enneagram? Do we have to enter the 7th level of the candy cane forest before we get the Enneagram? And when the facilitator explained the concept, I had an infinite number of annoying questions. "So you're telling me there is one number from 1-9 that defines me? And it doesn't change much over my life? And it came from childhood? Where is the double blind study? What's the p-value?" You can tell that I'm a riot at parties. The patient moderator politely listened to my "freshman-in-philosophy" questions and proceeded with the exercise. I got "typed" as a mix of 3 (Achiever) and 4 (Individualist). As kid who was raised to view success as one's source of value (3) and who had no friends but tons of curiosity growing up (4) it kinda' tracked. Over the years, the 30 minute exercise helped me a lot. I learned the the creative and strategic parts of the job (4) filled my bucket and I leaned into them. And I noticed when my (3) was causing me to care more about short-term comparisons for our company versus long-term success. We even used it as a leadership team. Like all companies, we had healthy friction between execs. Once folks learned more about what made each other tick, they were more understanding and collaborative. Enneagram is just one type of approach. MBTI and many others all have the same underlying theory. And heck - you can get to this level of self-knowledge without any framework too! I realize that for some founders and leaders, they don't need any of this introspective stuff. More power to them. I admire their ability to operate at 100% without any need for reflection or deep thought. They were, I guess, born to be entrepreneurial ubermensches. I'm surmising they had infinite energy for all activities and were good at everything. I'm only speculating of course as I can't see into their brains. The Problem of Other Minds, as they say. There I go introspecting again! 😂 I was never wired that way, so tools like these helped me.

How to Fail In B2B Sales: Poor Exec Alignment If you're a founder, a simple KPI for your personal impact on sales is simple: the # of client/prospect execs with whom you text. Too often, lack of exec alignment is a failure mode in B2B: * The Deal that Never Was: Salesperson works on a deal with a prospect's functional buyer. Everything is going "great." They needed it "yesterday." It's "down to formalities." Last day of the quarter: "the boss decided they need more time." * The Churn That Always Was: Exec sponsored the deal but wasn't involved. Deployment starts. Functional user in charge. Sets it up based upon his 100 requirements, none of which the exec cares about. Exec logs in 3 months before renewal and says "WTF is this?" Forgets why they bought in the first place. Surprise churn. How do you do it the right way? The best CROs know WAY more about it than I do, but here are some things that worked for us at Gainsight: 1. Mid-stage deal exec check-in from founder: Email (you usually don’t have a texting relationship at that point) to the effect of “I’ve heard our teams are working on a project to [business goals]. I’ve found most software deployments succeed or fail based upon alignment to the client’s business strategy. Do you have 15 min to make sure we understand your personal objectives? We’ve heard them from your team but would love to hear what’s on your mind.” Ideally do it as a phone call so it’s more intimate. Text afterward a thank you. If they text back, you now have a texting relationship. BTW if they write back to the email and say “I haven’t heard about this project” (which will happen), you’ll have good forecasting data! 2. Focus the call on them: It shouldn’t be about selling your product. What are the challenges they’re facing now? Asking in the right way is key. “What are your goals?” sounds naive. But something like “I’ve found that a lot of execs I talk to are struggling with showing the ROI of AI projects - is that something you’re dealing with?” demonstrates you’re an expert. 3. Make each call value add: What can you bring that truly helps them? An intro for the exec to a peer at another company? An article about a best practice unrelated to your product? 4. Don’t overuse: Be careful about contacting too many times. I’d say 1-2 in the deal cycle is plenty. 5. Kickoff call: Join the first implementation call and invite the exec. It’s so powerful when they share their vision to both teams. 6. Escalation: Get personally involved in escalations. Do not delegate. Send proactive regular updates on status. 7. See them: Go to events where you’ll bump into them. Fly to their office. Meet them at a local Starbucks. Don’t wait to be asked. “I’m in [their city] next week - you around for a walk?” Meet 100% of your large, early clients face-to-face. Those worked for us. Mileage may vary. Obviously none of that scales to a low end price point. But for high-value software, exec alignment is everything.

Trying to be a "real CEO" was one of my worst misakes: We launched Gainsight in May of 2013 and hosted our first ever Pulse conference for the customer success industry. The event would later become the standard, with thousands of annual attendees. I did my typical "cringe-but-lovable" thing and somehow ended up on the keynote stage in stunner shades. Later I had a football helmet on and did a really bad Heisman pose. You had to be there. Anyway, the event was a huge hit. I think people were endeared to our quirky culture. We raised more money that year and were on the path to being a real company. In January of 2014, we were four months from Pulse 2014. We were growing up and I wanted to too. So I hired a speaking coach to take my game to the next level. She was well regarded and very good at her craft. And she said: "Nick - you need to be more professional. No weird outfits. Speak slowly. And stop being so excited - it's strange. Also, read the script off of the prompter." So I did. And Pulse 2014 was BY FAR my worst keynote. I was robotic. My speech was forced. Very few smiles. A typical CEO speech. You can see it for yourself on YouTube. Actually, please don't! The next year, I went back to me. No script. No notes. My typical, frenetic, nerdy, corny self. Fired up. And yes - ridiculous props and outfits. Over the years I was: * A robotic man from the future * The wizard from Wicked * Ted Lasso * A kid from the Breakfast Club * And a rapper (who actually rapped on stage!) It worked. And damn it felt good to be myself again.

There are two warring theses to explain depressed stock prices for certain sectors (e.g., SaaS) right now: 1. They are undervalued with an unrealistically-low Terminal Value - BUY! 2. They are fairly valued or overvalued because AI will decimate their fundamentals - HOLD/SELL! I think there is a third alternative for consideration: 3. In a vacuum, these sectors are undervalued (i.e., Terminal Values will be higher). But the competition with AI isn't actually for business fundamentals - it's for capital. Economists Brunnermeier & Nagel (2004) had a paper (link below) about why "old economy" stocks were so underpriced during the dotcom bubble. It's worth a read. Their data showed funds had investors and if they had rotated out of the "hot" Internet sector too early and the downtrodden sectors didn't rebound quickly, their returns would have lagged and investors would have left. Capital needs are so huge for AI that the top model companies and related industries are soaking up a huge percentage of investor dollars. And if the belief is the IRR on these investments is massive or infinite (AGI/ASI), the logic is sound. If a fund reallocated dollars from AI to a fallen SaaS stock, for example, they would look dumb for a long time. Maybe so long that they'd shut down. This situation is perhaps even more stark today since many believe (including me) that AI isn't at all like the dotcom. If this is truly a fundamental change to humanity and economy, it's unclear why material capital would rotate out of it any time soon. I guess the crypto kids would say - 🤖🚀🌕

Over 13 yrs at Gainsight, I spoke to 3-5 people every week in Customer Success who were looking for a job (not at GS). 1000s over time. It gave me more feeling for what it's like to lose a job. Didn't prevent me from making cuts when it was the right call, but it helped me understand the impact better. Highly recommend leaders trying to help out a few people you don't know to find a job. Even in the optimist cases, there will be a lot of disruption coming and therefore a lot of empathy needed.

@dan turchin and I hosted our second AI ❤️ Philosophy dinner last night at the offices of @chemistryvc. It was such an incredible group - AI founders, investors and one actual philosophy professor (the rest of us were winging it!) The night's topics were (1) the possibility of eventual machine consciousness and (2) relationships and disconnection in the AI world. Some of my learnings from the brilliant humans that joined... * On consciousness, of course, we began with the standard questions - defining consciousness (we adopted the Nagel phenomenal experience version), debating the "problem of other minds" and "philosophical zombies" (Chalmers etc), understanding the hierarchy of conscious beings and the increasing circle of concern (Singer etc). * Ultimately, it was interesting to see the group bifurcate around axioms that were hard to debate. Being radically skeptical, I've never been able to fully get over the problem of other minds, so for me, I don't see a chasm between me accepting another human as being conscious and me eventually (not today) believing a machine could be conscious. By contrast, others had strong priors that only living beings can be conscious. * Some of this felt like a "substrate-dependent" argument, but folks had a hard time articulating what is "living" (i.e., DNA?) * My view is as humans incorporate more technology into their bodies, this line becomes fuzzier. * A compelling argument though was that the universe evolved biological life and biological intelligence. It didn't naturally evolve yet into machine intelligence. So there could be something unique on that path. And living beings all followed that path. This is a history-dependent argument. * The second group discussed the idea around AI, relationships and whether humans become even lonelier. They started with a strong axiom around human relationships being unique. I believe they even called themselves "team human!" * Always the skeptic, I didn't understand the logic. * However, what resonated for me was their follow-on point and that helped me think through the consciousness question. * There is something unique about a relationship (of any kind) between living beings - in that being A has emotion for being B and then B has emotion for A and so on. The recursive nature is what is special. Loving someone or caring about them isn't a 1-way idea. * In a trivial way, I love my dogs because they love me and they love me because I love them. Or maybe they're just dogs and they love everything! * By comparison, social media, parasocial relationships and perhaps AI today are 1-way. * Now, one day, I still think all bets are off if we start feeling like AI "feels" something about us - as friends or companions. The best philosophy discussions leave me with more questions than answers and this one was a doozy! Next one will be in April. We'll see if AI is conscious by then!

“In the midst of winter, I found there was, within me, an invincible summer.” - Albert Camus Before I re-enter my old social media world of AI takes that are irrelevant after 3 days and math memes that are immortal, I want to share some reflections from the last 2 weeks since our daughter Summer’s passing. I have felt more pain than I thought was possible. And I have felt more love than ever before. This love arrived in the form of messages and visits from precious friends and perfect strangers. People sharing stories of their own loss - of a child, of a parent, of a sibling. People opening up about near-loss experiences. People offering help for the little things. People coming by to distract me by talking about less-emotional topics like SaaS valuations. And people just checking in. The humans in my life also rallied toward the cause Summer asked us to support - The Trevor Project to reduce youth suicide. Between online donations and some direct ones, we’re around $600K toward our goal of $1M. More to go, but what a start: https://lnkd.in/g_R9RC39 Every person helped me immensely. But since grief is something most of us will encounter, I thought I’d share a few concepts that stood out as particularly healing. Each person grieves differently, so take these with a grain of salt: * There Are No Words, But They Still Help: “No words” was the most common phrase in my iMessages from the last week. I know it’s so hard to know what to say. But for me, simply hearing from people made me feel seen and loved. * Learn from Loss: Summer never believed she mattered. Yet the ~100 classmates from her school told so many tales of her impact. Being vulnerable, I struggle with the same inner critic Summer did. Hearing her friends celebrate her life woke me up woke me up to the fact that I matter too. * Embrace Choice: Several friends that experienced loss talked about treating our path from here as a choice. We didn’t choose what happened to us. But we grieve because we love. And I choose to love Summer for the rest of my life. * Do It for Her: On that note, a longtime peer in the business world spoke about creating a mission for yourself. In his case, he wanted to live a life that would have made his lost mother proud. For me, I committed to helping me and my family live lives full of purpose and passion, in honor of Summer. * Find a Way to Process: People described the ways they processed their own grief - through travel, art, music and more. For me, I’ve been through a number of tough personal experiences over the last 3 years and found that writing poetry has helped me. Below is one I wrote about the unfinished nature of sudden loss. I hope we can all find ways to shepherd each other through the unfinished sentences of life - and give ourselves grace that whatever words we choose are perfect. ❤️

One of the biggest things B2B startups miss is underselling the "personal ROI" to the buyer or user of your technology. I spent time with a leadership team of a B2B startup yesterday and the topic of demonstrating ROI came up. We talked about how a natural motion is to convince the buyer about the "business ROI" - e.g.,: * Reduced costs * Higher revenue growth * Increased compliance/security * etc. And naturally, users often assess products on "functional ROI" - e.g.,: * Less effort * Simpler UX * Better integrations * etc. What I think many founders miss is the opportunity to make sure you're also appealing to the buyer's "personal ROI." What's in it for them as humans? Humans at work want: * To get promoted * To not get fired * To get home on time * To feel recognition and pride * To avoid shame * etc. Your products likely help with some or all of the above, but you might be underselling yourself. And ultimately, it's often the "personal ROI" that causes a deal to go from "that's interesting" to "I'm ready to buy." You have to be subtle about it. It can't be in your slides or on your website. But talk about other customers who use your product and casually mention the ones that got promoted. Create content that appeals to the career ambitions of your clients. Make sure your product includes reports or dashboards that your user can show to their boss to demonstrate the good work that they are doing. Humans buy software. That is until agents buy software. For now, "personal ROI" is something to consider in your pitch.

How do you grow your Average Contract Value (ACV) in a B2B business and not get stuck in "no man's land" of $20K ACV with sales-led growth that kills so many companies? I brainstormed with a super-smart B2B AI founder about this today: * On the core premise, so many SaaS companies got stuck in the following pattern. Build product for SMB/mid-market. Focus on sales velocity, so product innovation is limited. Early pitch is "we're simpler version of [up-market competitor]." Get fast customer traction with poor CAC economics. ARR growth overshadows this. Eventually (1) mid-market customers "graduate" to the enterprise solution, (2) lower-end, more comprehensive SMB platforms soak up new logo growth, (3) ARR flattens. This has happened to thousands of SaaS cos over time. You get squeezed. And all of that is now easier with agentic coding! * Play 1: Go Wide (e.g., Rippling or Hubspot a few years ago). Keep investing in R&D to add modules. Raise a lot of money. Solve more problems for the client. Don't move up-market too fast. Stay focused. Keep product simple but offer more modules. ACVs rise with more things to sell. Customers naturally grow. NRR expands over time. Economics work. TAM expands. * Play 2: Go Up (e.g., Decagon, Sierra). Solve problems for bigger and bigger customers. Scale R&D for more unique needs of large customers. Invest in FDEs. Don't get distracted by SMB-focused competitors. Logo count doesn't matter. Huge deals do. Sales cycles can be longer upfront (though still fast in the AI era) but worth it, given the sizes. Hire a high end sales force. Offer longer ramps and pay up. Invest in brand marketing. ACVs grow as customer size grows. NRR grows through expansion across divisions within large companies. The decision to go up or wide is scary. It can feel easier to stay true to your first product, keep it simple and just invest in sales reps. It's indeed simpler easier until you hit the wall of growth.

One thing that’s interesting in the AI Apps world these days - everyone competes with everyone. And for customers, it's confusing to figure out the right approach. For example, if you're trying to grow your pipeline, do you? * Buy an AI SDR tool? * Use an agentic CRM tool which can also do outbound? * Buy an agentic marketing platform? * Use an AI GTM platform like Clay? * Leverage an existing tool's AI capabilities (e.g., Salesforce, martech platform)? * Vibe code a tool? * Use agentic coding to build something? * Build on an agent builder platform? * Extend native LLM capabilities? In some ways, it's overwhelming for the buyer and this creates inertia and churn. A critical thing for AI founders is to put yourself in the customer's shoes and not just consider your direct competitors but also alternative solutions to the customer's problem.

One important consideration in the "future of software" debate is the "future of companies." What seems obvious to me is that businesses are changing at a greater rate than ever. Whether it's responding to macro turbulence (e.g., tariffs), disruptive competitors or opportunities enabled by AI, the pace seems to be accelerating. One problem with technology historically (whether built or bought) is that it often became frozen in time. A company would have a business need and either purchase third-party software or build tooling based upon that need. Over time, the business' needs would drift and the software would become less and less valuable. Users would gut it out, because the rate of change wasn't fast. Eventually, a new leader would come in and say "why did we buy/build this piece of $@!#?" And they would put out an RFP for a new third-party or custom-built solution. The cycle would start over. The problem is that companies are evolving at light speed. 2 years ago, "agentic" wasn't on almost any company priority list. Now it's everywhere. Repatriation of workloads from the cloud were unthinkable less than a decade ago. Now hybrid multi-cloud is the norm for large companies. Geopolitics were complex but the times of turmoil had been long forgotten. Companies can no longer afford to have frozen systems. So the only question in my mind for any project is simply - which gives a business the most agility and optionality. If there is a tech disruption, can they respond in a week? Or does it take months? Corporations were never built to move this fast. Now they have to. And software will need to as well.

Spoke to a CEO of a $140M ARR SaaS co yesterday. Profitable. Growing modestly. But churn is a big issue. The old playbook used to be to retain customers by: * Building a great product * Managing quality and uptime * Delivering rapid time to value * Ensuring strong adoption * Verify value and outcomes with your key stakeholders What's concerning now is many SaaS cos of all sizes (from AI native to mature) are experiencing churn even for customers that check all of those boxes. The work right now is to rethink your value proposition and reason for existence - not just shuffle deck chairs on the Titanic. This is not a Customer Success or CRO problem - it's a founder/CEO challenge. The captain needs to lead. Companies like Intercom show it's possible to not only avoid the glacier, but glide into open seas. But keep "sailing faster" at your own peril.

Be Curious: 5 Weak and 5 Strong Questions to Ask B2B Customers: Everyone in B2B, whether you're a brand new AI startup founder, an experienced software exec or a customer-facing individual contributor, wants one thing - stronger customer relationships. In a world where software is a commodity, relationships are often the difference between a win and a loss, a "closed" and a "not now" or a renewal and a churn. I've written about techniques to meet with customers. But what do you say when you see them across the Zoom screen or Starbucks table? I've been there when I asked the weak questions that showed a lack of curiosity, no point of view and no confidence: 1. "What's your feedback on our product?" (maybe they didn't even try it) 2. "What feature do you like the best?" (the buyer may have no idea) 3. "How do we compare to our competitors?" (me me me) 4. "What are your goals?" (as if the buyer wants to just open his/her OKRs and share them) 5. "Are you ready to buy this quarter?" (umm...) The common thread between those weak questions is that they are about you, not the customer. By contrast, there is a plethora of powerful questions the best ask. I've stolen many, including: 1. "I was able to meet with a dozen CIOs last week. Every single one seems to be struggling to figure out the productivity impact of AI. How are you handling that? I can even send you a survey we did around this." (shows you have expertise) 2. "I noticed your team was called out in the last earnings call in a good way. That's amazing. How did that make you feel? What are you doing to sustain the work?" (shows you're paying attention) 3. "I'm hearing more and more that this budgeting season is hard since 2027 is so murky. How are you approaching prioritization?" (shows that you get the real world) 4. "I can only imagine how many vendors you get pitched by about AI. Who are some of the best partners for you and what are they doing to truly help you?" (shows you want to be a true partner too and are open to feedback) 5. "Ultimately, software - including ours - are just tools. I've found that the real impact comes in making sure its rolled out aligned to the client's goals. Is there one company priority that you heard about in your CEO's all hands that we should align around for the deployment? Is there a milestone where a win by then would help the company?" (figure out how to strategically ladder up and start identifying a compelling date) As one of the all time great entrepreneurs said, it's about being curious...

Me in every Board Meeting at Gainsight: "Our biggest problem is pipeline!" Board (inner monologue): "Other than that, how was the play, Mrs. Lincoln?" I've spoken to so many founders (including conversations with myself) where we all get stuck in a very boring version of "Groundhog Day": * Miss sales target * Sales says pipeline is low * Put pressure on CMO - "I need more leads!" * Send more emails! * Spend more on paid channels! * Get a new agency for demand gen! * Find a new PR firm! * Look for a new CMO I've gone through that entire cycle way too many times... Sometimes, it is indeed an execution issue. Often it's a strategy one. I now try to ask myself these three questions: 1. Is our Ideal Customer Profile (ICP) granular? Or is it "everyone"? 2. Do we truly understand the size of the market that is ready to buy now? Or are we working off of fantasy TAMs? 3. Is our brand and message differentiated or are we just throwing dollars into the void? Pipeline is often a symptom - not the root cause.

I like the discussion of the "transition" period for AI in this article. It's possible that AI takeoff is slow and adjustment is easy (though that might be bad for current AI equity values!) It's possible that AI takeoff is fast and all of the productivity gains are reinvested, so we enter a utopia quickly. But it's also possible that AI takeoff is fast but there is an adjustment period that's hard (e.g., firms initially use AI to cut costs en-masse because of a lack of confidence in the future). We definitely need to talk more about that path so we're prepared. No one knows what is going to happen - that's the honest truth. So being ready for multiple scenarios is imperative.

So proud of Chuck Ganapathi and the team completely reinventing and refounding Gainsight and the CS space. Big things coming. Gainsight (Chuck's Version) will be the best era yet!

"The One Where a Famous VC Made Me Cry - And I'm Grateful": The year was 2002 (OK, Boomer!) My first startup (Chipshot) that we founded in our dorm rooms went from hot to not and shut down in 2000. The next startup (XDegrees) that I joined shut down 18 months later. I was 25 with a big ego and no money. One of our startup's VCs was a legendary investor. I pinged him to get career advice and he kindly accepted. I went to his office - incredibly a tiny little room with space for 2 uncomfortable chairs. I awkwardly sat and handed him my printed resume (remember kids - this was a LONG time ago...) [VC with no eye contact]: "Nick - I look at your resume and see... Chipshot: FAILURE... XDegrees: FAILURE... you'd better watch out or people are going to see you as a serial FAILURE. Go somewhere where you won't FAIL.” I politely thanked him and went back home. And bawled. There were some serious young man tears landing on my IKEA patio swing that night, people. Yet the next morning, I decided to listen to his advice. I cold emailed some already successful companies and ended up getting a PM job at one. I started on probably the most boring software product in the world, but at least it didn’t go out of business! Eventually I became a VP and GM and subsequently got to restart my dream of startups and founding companies. What do I take away from this? Well, none of us know the counterfactual. Maybe if I had ignored the investor’s 2002 advice, I would have gone on to start some epic trillion dollar company. Maybe. But 24 years later, I’m grateful that the investor had the guts to step beyond the bounds of politeness to share what he thought I needed to hear. And I work to be that candid (perhaps with a bit more bedside manner!) with others. Easier said than done.

I’ve reflected on this Christmas tweet from @karpathy for the last month or so. And I think it captures one of the biggest challenges we’ll face in adapting to this new world - handling change. I don’t know about you, but I feel behind every day these days. No matter how many native X posts I bookmark with laudable intentions of reading them, no matter how many AI startups I flag to check out, no matter how many research papers I open to read, I can’t keep up. The pace of change is just too fast. The common adage is to embrace change - “change is the only constant” and so on. Heck - one of Gainsight’s values that we chose was Shoshin (Beginner’s Mind). Yet… * Being a Beginner every so often in subsets of your life can feel empowering. Feeling like a noob in all domains every day can be daunting. * Sometimes, it can seem futile to try to learn, knowing that the latest thing might be irrelevant tomorrow. Remember Ralph with Claude Code? Sora? Prompt Engineering? They appear like concepts from another era, yet they were weeks and months ago. And investing time to check out the “new thing” can in hindsight seem like a waste. * Deeper still, the daily change isn’t just a change in skills - it’s a change in identity. One of the most powerful aspects of how we see ourselves is as “a person who…” I’m "a person who..." can start and lead companies, a person who knows a lot about customer retention, a person who is excellent at cheesy parody videos. But one day, each aspect of who I am becomes less unique in the face of AI. Don’t get me wrong. I’m fighting the good fight. I’m reading everything I can. I have 3 Claude Code sessions open as we speak. I constantly listen to AI podcasts as I walk around. I love learning. I love being a beginner. But I know I’m losing ground and getting held back in school each day. I suspect this is how many people - even outside of programming - feel. A huge project for humanity is to understand new ways to adapt to change - to our knowledge, to our skills and to our identity.

[This post is very heavy] “There are moments that the words don't reach There is suffering too terrible to name You hold your child as tight as you can And push away the unimaginable” “It’s Quiet Uptown” from Hamilton Last Tuesday, the unimaginable happened. We lost our 17-year-old daughter, Summer Devi Mehta. Unimaginable suffering. Unimaginable grief. Unimaginable fog. We held her tight for so long, with the help of so many. But ultimately, it wasn’t enough. But yet, equally unimaginable was the love. We hosted a celebration of life on Saturday, which we called “Summer Lovin’,” after the song “Summer Nights” from the musical Grease (we are all theater nerds here). About 100 of her classmates, teachers and staff joined our family and we heard countless tales about how Summer impacted the lives of others in big ways and small. One person told us that Summer lived a more vital existence in 17 years than most do in 100. To that end, Summer’s last wish was to raise $1M or more for the Trevor Project, with the goal of reducing youth suicide and having fewer stories end in such an unimaginable way. Check out Summer’s story and donate, if you choose, here: https://lnkd.in/g_R9RC39 We felt so much caring from the community and recommitted to living our lives with heart and purpose, as Summer did. On Friday, we handled the most painful task of cremating her remains. After the ceremony, we went to Half Moon Bay and stared out into the ocean. I imagine Summer’s spirit riding those waves into peace. The final lines of “Summer Nights” capture how we feel now: “Summer dreams ripped at the seams But, oh Those summer Nights! (Tell me more, tell me more, more, more)”

This essay on AI and economic impact is making the rounds. I appreciate the level of detail the authors have put into the predictions. It's a compelling read. All of us are biased by our Bayesian priors. For me, I have a belief that humans will not let this dire scenario play out and that we have systems that naturally course correct. In particular, I see a few levers to prevent the economic doomsday: * Monetary: The magnitude of rapid economic transition in the post would result in massive deflation, I believe (there is asterisk that the capital needs of AI could offset deflation). To the extent we see deflation, the Fed would have a clear mandate to drive stimulus, QE, etc. In addition, the impact would be global, so I couldn't imagine the dollar faring worse than other countries (especially given US military strength). The Fed is able to react more quickly than policymakers (see Lehman Brothers for an example). * Fiscal: People wouldn't go down without a fight. The authors allude to this but I think popular demand for direct support would explode. * Prices: A significant factor in deflation is that the cost of living would plummet, making government support easier. I do think we will see asset price dislocation no matter what, but it's not obvious it will be across the board. One red team to the post's scenario of broad-based declines is we will see some sectors soar (e.g., semis continuing to rise, energy, data center infrastructure) and others plummet. Given the percentage of US assets in broad-based indices, there is some natural rebalancing that occurs. I have no idea what will happen, but it's certainly a time to have the conversations.

Story time: How a $10 toy Porsche saved a $10M TCV customer for Gainsight. People often ask me about how to retain B2B customers. The short answer is there is no one magic answer - it's really hard! And it's getting tougher. But I think we often underestimate the importance of the human connection in all of this. In 2017, we were ~$30M of ARR. Because our category was new, every new sale was a fight against inertia. And that battle didn't stop with the contract. In the summer of that year, our champion at one of our highest-profile clients, a $200K ARR customer, texted us. Something to the effect of "the new C-level doesn't know what Gainsight is and wants to rip it out." I didn't blame him - most executives had no clue who we were! The champion gave us a list of like a 100 features we needed to fix to keep the customer. He said the executive would churn us otherwise. It didn't add up to us. How would a bunch of random reporting features cause this new boss to change his mind about us? So I started hunting for connections. The exec came from outside of tech, so our shared links were thin. Eventually, I cold emailed him - asking for 15 minutes of his time. I vividly remember where I was when I got him on the phone - walking on Florence Street in downtown Palo Alto. He was super nice but understandably busy. I'm sure talking to a niche vendor was low on his list of priorities. I told him what we did and he politely listened. And then the call ended respectfully. I didn't get good vibes. But I did pickup one piece of useful information. In the chit chat upfront, he shared that he loved racing cars. So I sent him a toy sports car off of Amazon. YOLO right? He reached out a week later and said he wanted a detailed briefing on us. We understood his vision and evolved the deployment to his strategy. He brought in more leaders from the company. And eventually, he expanded from $200K to $3M/year for a > 3 year term. We became friends and he's truly one of the warmest execs that I've met. He joined our advisory board. He spoke at countless events. And he'd say to this day that the little cheap plastic automobile was the accelerator for the customer relationship. Many Gainsters from that era remember the story to this day. Listening to your clients and showing them that you care about them as a human never gets old.