Learning From Business Failures

I've watched 3 "revolutionary" healthcare technologies fail spectacularly. Each time, the technology was perfect. The implementation was disastrous. Google Health (shut down twice). Microsoft HealthVault (lasted 12 years, then folded). IBM Watson for Oncology (massively overpromised). Billions invested. Solid technology. Total failure. Not because the vision was wrong, but because healthcare adoption follows different rules than consumer tech. Here's what I learned building healthcare tech for 15 years: 1/ Healthcare moves at the speed of trust, not innovation ↳ Lives are at stake, so skepticism is protective ↳ Regulatory approval takes years usually for good reason ↳ Doctors need extensive validation before adoption ↳ Patients want proven solutions, not beta testing 2/ Integration trumps innovation every time ↳ The best tool that no one uses is worthless ↳ Workflow integration matters more than features ↳ EMR compatibility determines adoption rates ↳ Training time is always underestimated 3/ The "cool factor" doesn't predict success ↳ Flashy demos rarely translate to daily use ↳ Simple solutions often outperform complex ones ↳ User interface design beats artificial intelligence ↳ Reliability matters more than cutting-edge features 4/ Reimbursement determines everything ↳ No CPT code = no sustainable business model ↳ Insurance coverage drives provider adoption ↳ Value-based care is changing this slowly ↳ Free trials don't create lasting change 5/ Clinical champions make or break technology ↳ One enthusiastic doctor can drive adoption ↳ Early adopters must see immediate benefits ↳ Word-of-mouth beats marketing every time ↳ Resistance from key stakeholders kills innovations The pattern I've seen: companies build technology for the healthcare system they wish existed, not the one that actually exists. They optimize for TechCrunch headlines instead of clinic workflows. They design for Silicon Valley investors instead of 65-year-old physicians. A successful healthcare technology I've implemented? A simple visit summarization app that saved me time and let me focus on the patient. No fancy interface, very lightweight, integrated into my clinical workflow, effortless to use. Just solved an problem that users had. Healthcare doesn't need more revolutionary technology. It needs evolutionary technology that works within existing systems. ⁉️ What's the simplest technology that's made the biggest difference in your healthcare experience? Sometimes basic beats brilliant. ♻️ Repost if you believe implementation beats innovation in healthcare 👉 Follow me (Reza Hosseini Ghomi, MD, MSE) for realistic perspectives on healthcare technology

Case studies are great, but I often learn more from the dumpster fires. I don't think I'm alone. Last week's CMO Coffee Talk featured a variety of rebrand experience shares, and the vast majority of the most valuable lessons and takeaways came from mistakes. Even when you see, read or hear case studies presented, some of the most common questions are: ✔️ What would you do differently next time? ✔️ What do you wish you had known before starting the project or process? ✔️ What went wrong and what did you learn from that, and/or how did you pivot because of it? These all focus on lessons burn of failures. James Clear, author of Atomic Habits, says as much: "Stories of failure resonate more than stories of success. Few people reach the top, but everyone has failed—including those who eventually succeed. If you're teaching people how to succeed in a given field (or talking about your own success), start with how you failed." Most companies have case studies prominently featured on their Web sites and sales materials. What if you also included customer failures? We tried this once in a webinar series and it worked spectacularly. It exclusively targeted stalled opportunities - prospects who for some reason or another just weren't moving forward. We called the series "Customers Unplugged" or something like that. And in a live Q&A format we asked HARD questions. Things like: 💣 What do you regret about buying this product? 💣 What do you need new customers to know before they commit? 💣 What were some of the reasons you almost didn't buy? The exec team was terrified when we first proposed this. And yet, after each one we did, at least 3-4 large deals suddenly got unstuck. The world is not full of purely success stories. No prospect is going to believe your case studies represent 100 percent of your customer base. Be vulnerable to earn loyalty. Let more people hear your dumpster fires! I guarantee it will attract far more than it will repel.

Have you ever written a personal Failure Log? It’s a simple but powerful self-improvement technique which builds mental resilience. Setbacks happen in everyone’s career journey. But documenting the decisions and circumstances that lead to failure will let you transform defeats into lessons and strengthen your capacity to bounce back. It’s easy to do too. Here’s how to write a Failure Log: Pick a format (spreadsheet, notebook, or digital journal) and a frequency (weekly is good for reflection). For each entry, answer: - What went wrong? - What did I learn? - How will I change my approach next time?   Use one or two sentences to answer each question. Stay objective. Use a neutral tone (“I didn’t delegate enough tasks”) rather than inflammatory statements (“I’m terrible at managing projects”). Focus on describing events and lessons, rather than beating yourself up. The aim is insight, not self-blame. Review your entries every month or two to spot patterns — maybe you sometimes underestimate timelines or often fail to communicate well enough with stakeholders. Over time, you’ll course-correct with consistent strategies. Celebrating your successes is important, but objectively acknowledging your failures will often yield the most impactful lessons. A Failure Log can be a transformative tool to consistently improve your outcomes. Best of all, over time you’ll develop a more resilient form of confidence — grounded in reality, not wishful thinking. What techniques do you use to learn from your own professional setbacks?

This AI wellness app got 100 signups on launch day. But 3 weeks later, zero users were left. The founder couldn’t understand what went wrong - until he realized he hadn’t opened the app himself in weeks. Here’s what happened: He built an AI-powered app that analyzed blood diagnostics and gave personalized wellness tips. It was sleek. Smart. And technically impressive. But it failed - fast. Here’s why: ▶︎ 1. He ghosted his own product. As a mentor, I asked him, “When’s the last time you used your app?” He paused. “Not in a few weeks”. If the founder doesn’t believe in the product, users won’t either. ▶︎ 2. There was no expert in the loop. The app offered wellness tips based on blood diagnostics. But there was no medical advisor, no human credibility, no context. In healthtech, if users don’t see who stands behind the advice, they simply won’t follow it. ▶︎ 3. He avoided regulation - then lost user confidence. By calling it a “wellness” app, he sidestepped FDA scrutiny. But that also meant he couldn’t make strong claims. No outcomes. No promises. The result? Vague tips, low trust, zero retention. ▶︎ 4. He focused on tech, not value. It was AI-powered, yes. But not human-centered. No nudge to follow up. No context. No loop to make users come back. So here’s how we fixed it: → He became user #1 - experiencing every friction point firsthand. → Simplified the experience around one real, everyday user goal. → Added medical advisors to review recommendations. → Reconnected with early users to gather unfiltered feedback. Three months later: Retention went from 0 to 18%. And 1 in 5 users started referring a friend. If you’re building in healthtech, remember: Slick dashboards don’t build retention. Trust and clarity do. So what’s the one change you made that finally got users to stick to your product? #entrepreneurship #healthtech #funding

HealthTech isn’t SaaS with a stethoscope. That mindset is why startups fail. I get it. You come from SaaS. We all follow the SaaS playbook. Investors evaluate and measure on SaaS. The books written for SaaS that appear to translate to every industry. Onboarding flows, growth loops, and funnels. You build something slick. Raise a decent round. Secure your first pilot. Then... silence. The product works. The results are good. But no one moves. Weeks pass. The pilot drags. The clinical lead stops replying. The buyer’s changed roles. And procurement? Don’t even ask. SaaS playbooks often collapse in HealthTech. Not because your product is bad. Because our assumptions are wrong. We’re building for velocity. Healthcare operates in inertia. We optimise for activation. They optimise for avoidance of risk. You want fast feedback. They give you silence, until the regulator, the lawyer, or the clinician gets involved. If you're building in HealthTech: The buyer is not the user. The user is not the decision-maker. The person trialling your product often can't say yes. But they can absolutely say no. You are not selling to individuals with discretionary budgets. You are selling into systems. Messy, overworked, risk-averse systems. This means: Procurement isn’t “slow” - it’s paralysed by legacy software, compliance burden, and political risk. Clinicians don’t “resist innovation” - they resist anything that adds clicks to their day. Outcomes don’t “speak for themselves” - they need real-world validation, peer-reviewed proof, and institutional backing. So what actually works? Who can block you? Who needs to be convinced? Build for the boring stuff: Integration, IT approval, commissioning pathways. Lead with evidence, not enthusiasm. Case studies, cost savings, compliance fit. If you’re still pitching like it’s a SaaS sale, start again. Because HealthTech is not a category. It’s a system. And systems don’t reward speed. They reward staying power.

The "High Performer" who is also a "Low Trust" individual is the single greatest threat to your organization’s long-term viability. In my three decades of navigating corporate structures—from the early days of Software programming to today’s "Intelligence First" AI era—I’ve seen one mistake repeated across every industry: Valuing the "what" (#performance) while ignoring the "how" (#trust). Simon Sinek famously illustrated this using a Navy SEALs metric: Performance: Skills on the battlefield. Trust: Character off the battlefield. The SEALs, one of the highest-performing organizations on the planet, would rather have a Medium Performer of High Trust than a High Performer of Low Trust. Why? Because the latter is a toxic leader. They are the "performance superstars" who deliver results while simultaneously destroying the morale, psychological safety, and culture of everyone around them. The Lopsided Metric Trap In business, we are obsessed with measurement. We have millions of KPIs for quarterly earnings, delivery velocity, and ROI. But how many organizations have a rigorous metric for trustworthiness? When we promote based solely on numbers, we are often "bonus-ing" toxicity. This creates a culture where: Short-term gains mask the rot in the team’s foundation. Top talent leaves, not because they can’t do the work, but because they refuse to work for an "asshole." Innovation dies because trust is the prerequisite for the risk-taking required in AI and digital transformation. If you are leading a team today, you must address toxic behavior regardless of the performance metrics. A leader who hits every target but leaves a trail of broken spirits is not a leader—they are a liability. Protect your #culture. Protect your #people. The "High Trust" individual is the one who has your back when the chips are down. They may not always be your #1 individual contributor on a spreadsheet, but they are the reason the rest of the team performs at a 10/10. My challenge to you: Go to your team and ask two questions: "Who do you trust more than anyone else?" "Who is the person creating a toxic environment?" They already know the answers. The question is: Do you have the courage to act on that intelligence? Don’t let short-term gains blind you. Your company’s future—and your legacy as a leader—depends on the trust you cultivate today. DC* #Leadership #Culture #Trust #Strategy #DINWINS #IntelligenceFirst #Management #SimonSinek #OrganizationalHealth

Early in my career, when I shared the story of a workshop that completely bombed (an email announcing layoffs arrived in everyone's inbox during day 1 lunch of a two-day program -- and I had no idea how to handle this), three women immediately reached out to share their own "disaster" stories. We realized we'd all been carrying shame about normal learning experiences while watching men turn similar setbacks into compelling leadership narratives about risk-taking and resilience. The conversation that we had was more valuable than any success story I could have shared. As women, we are stuck in a double-bind: we are less likely to share our successes AND we are less likely to share our failures. Today, I'm talking about the latter. Sharing failure stories normalizes setbacks as part of growth rather than evidence of inadequacy. When we women are vulnerable about their struggles and what they learned, it creates permission for others to reframe their own experiences. This collective storytelling helps distinguish between individual challenges and systemic issues that affect many women similarly. Men more readily share and learn from failures, often turning them into evidence of their willingness to take risks and push boundaries. Women, knowing our failures are judged more harshly, tend to hide them or frame them as personal shortcomings. This creates isolation around experiences that are actually quite common and entirely normal parts of professional development. Open discussion about setbacks establishes the expectation that failing is not only normal but necessary for success. It builds connection and community among women who might otherwise feel alone in their struggles. When we reframe failures as data and learning experiences rather than shameful secrets, we reduce their power to limit our future risk-taking and ambition. Here are a few tips for sharing and learning from failure stories: • Practice talking about setbacks as learning experiences rather than personal inadequacies • Share what you learned and how you've applied those lessons, not just what went wrong • Seek out other women's failure stories to normalize your own experiences • Look for patterns in women's challenges that suggest systemic rather than individual issues (and then stop seeing systemic challenges as personal failures!) • Create safe spaces for honest conversation about struggles and setbacks • Celebrate recovery and growth as much as initial success • Use failure stories to build connection and mentorship relationships with other women We are not the sum of our failures, but some of our failures make us more relatable, realistic, and ready for our successes. So let's not keep them to ourselves. #WomensERG #DEIB #failure

In school, we’re taught that failure is something to avoid at all costs. But failure is actually required to reach your long term goals. Here are 5 ways failure helped me reach mine: 1. Building A Music Blog In 2011, I started a music blog. It never got more than 200 total visits. I eventually shut it down. But it taught me how to set up my own website and the basics of internet marketing, which allowed me to start Cultivated Culture without any funding. 2. Building A Social App In 2014, I had an idea for an app. I spent dozens of hours mocking it up and $1,000+ on prototype. Two weeks later, two other companies launched identical apps with venture funding. But it taught me the basics of developing a piece of software, and allowed me to build our current suite of job search tools. 3. Freelancing I wanted to change industries, so I freelanced to gain experience. I didn’t get any clients from the first 1,000+ emails I sent. But it taught me that “sales” and outreach are volume games, as well as giving me data that I eventually used to optimize, get clients, and leverage in my networking efforts to land referrals. 4. LinkedIn (Take 1) I shared my first piece of LinkedIn content in 2016. I did it for about two weeks before feeling dejected that I wasn’t getting any reactions or views. That eventually led to the realization that, if I wanted to grow, I needed to focus on creating content instead of outcomes at the beginning. 5. LinkedIn (Take 2) About six months later, I starting sharing LinkedIn content again. This time, I kept it up for a month before running out of ideas. I had to stop again, but it eventually taught me that creating content is about building a repeatable system vs. just writing when inspiration strikes. 6. The Outcomes Of Failing Every one of these failures taught me lessons that I eventually leveraged successfully down the road. I was able to start my own business and bootstrap it without needing funding or paid ads because of everything I’d learned from past mistakes and failed ventures. Every one of those experiences is a lesson, if you’re open to seeing it.

Everyone wants success, and almost no one seems to talk about the failures that got them there. A rejection, job loss, or decision you wish you could redo feels deeply personal. It's easy to see these moments as proof you're not as capable as you thought. But what if those moments aren't verdicts on who you are, but chances to adjust course? In my latest newsletter, I explored how to turn failure into forward momentum instead of letting it define you. Four shifts that make the difference: 1️⃣ Treat failure as data, not identity If you interpret every setback as evidence you're not good enough, you'll hesitate to take future risks. Treat those same setbacks as feedback that sharpens your strategy. 2️⃣ Study the system until it becomes instinct Most rejection isn't about your talent - it's about understanding the unwritten rules. Reverse engineer what decision-makers actually reward, and patterns start to become clear. 3️⃣ Own the narrative before it owns you When you're transparent about missteps and what you learned, you control the story. Instead of being quietly defined by a setback, you demonstrate growth through reflection. 4️⃣ Separate what happened to you from what you chose Some setbacks are beyond your control. Others stem from decisions made under pressure or scarcity. The latter are painful to examine, but they provide the clearest path to better judgment. Failure doesn't automatically become success, either. It becomes success when you engage with it deliberately, extract the lesson, and apply it to your next move. I wrote the full breakdown in my newsletter here, and it's worth sharing with anyone in your network navigating a setback right now.

After 11 years at Dropbox & Asana, I’ve seen one pattern crush more PLG companies than anything else: premature sales hiring. Companies see a few hand-raisers and then rapidly build an enterprise sales team. Six months later: weak pipeline, frustrated reps, and a compromised PLG motion. Instead, here’s how to scale Product-Led Sales (PLS) without killing your growth engine: ✋ Step 0: Wait for Hand-Raisers Resourcing: 1/10 (mainly patience!) - Respond to organic demand: users asking to “buy more” or “buy for my team” - Add “Contact Sales” CTAs (pricing, billing, nav), close deals at your “sales floor” (~$10K+, around credit card limits) - Graduate when you have enough inbound for one FTE 💡 No hand-raisers? Don’t hire sales. Improve your PLG motion first. Once you have enough hand raisers, you can layer on three different PLS mechanisms: 🌱 Land & Expand with Product-Qualified Leads (PQLs) Resourcing: 3/10 (ops + inbound sales) - Score users on buying intent via firmographics + product usage, route top leads to sales - Encourage work emails, enrich domains, layer usage signals (activation, $10K+ spend trajectory), iterate scoring over 12-18 months - Most successful when users are also buyers (devs, designers, analysts), fails when users lack buying influence 💡 Lowest resource investment, highest success rate when persona fit is right 🐸 Leapfrog: Turn PLG Traffic into Sales Leads Resourcing: 5/10 (web, CRO, PMM, Sales Enablement, Sales) - Create parallel enterprise paths without disrupting self-serve - Add dual CTAs (“Start free” + “Talk to sales”), optimize sales forms for lead quality not volume, build buyer content (demos, ROI calculators, security pages…) - Most successful with high web traffic, fails when you over-pivot to enterprise and erode PLG funnel 💡 Scales enterprise pipeline faster than organic PQLs but requires new value props and enablement 💬 Leverage Brand & Product for Executive Access Resourcing: 10/10 (outbound marketing & sales) - Use product & company rep to independently engage senior buyers - Host conferences with executive tracks, leverage champions for leadership intros, launch exec demand gen campaigns… - Most successful with dual personas (junior users + senior buyers), strong brand halo & senior exec value prop, fails when you hire sales leaders without PLS experience or create PLG vs Sales attribution wars 💡 Highest investment & biggest deals, but requires right leadership and org structure Bottom line: don’t just ask “when should we hire sales?” Ask “what assets does my PLG motion give me to work with?” The answer is your roadmap.