Rob Kischuk

Introducing "Confessions of a Builder" 🏗️ The road to building your own business is incredibly challenging. In my new newsletter, "Confessions of a Builder," I write openly about the challenges, mistakes, successes, and, most importantly, the personal journey through it all. 🔗 More specifics in the link provided. I hope you join me as we explore how to build wiser, faster, and smarter together. #Entrepreneurship #StartupJourney #ProductInnovation #GrowthMindset #Leadership #ConfessionsOfABuilder

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Does negotiating with development agencies feel like a puzzle? It doesn’t have to! On this week's SaaS Founder Stories, I chatted with Kurt Willis from Boro Dev Agency, LLC. We talked about how to align your tech needs, investor expectations, and development goals. His biggest lesson? Transparency and flexibility are key to a successful partnership. If you’re scaling your SaaS and working with dev teams, this episode is a must-listen. 💡https://lnkd.in/gU88cK8E #SaaS #TechLeadership #StartupGrowth #DevAgencies #StartupAdvice

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I spoke with developers recently. They were telling me their pain points when it comes to waterfalls and distributions. They underwrote a deal in which they’ll make a profit for a few years, then do construction (which they’ll raise more capital for), and after that, they will refinance and hold for 10-15 years. Their issue is that their returns and IRR for both the GP and LP weren’t adding up. I brought up a few good points for them to start looking into and asked them how they would solve these issues. Was their model created for construction and to handle multiple capital injections? What happens when you have different investors contributing at different times? When is capital being returned? All of these issues are common occurrences and need complex solutions to resolve. Everyone wants a simple waterfall, but every case is unique. How do you answer these questions when you are underwriting? If you need help structuring and organizing these types of distributions, reach out and let’s chat. --- If you found value in this post, please like and comment. Follow for more content! If you want to receive my newsletter, direct message me! Any distribution or waterfall questions? Reach out! Need help setting up or calculating a waterfall? Reach out.

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Few agencies without a technical lead are able to get by (and none thrive). Relying on contractors can be a double-edged sword: they bring specialized skills but often lack a cohesive vision that aligns technology with your customer’s long-term goals. This disconnect results in software bloat, where unnecessary features and technical debt pile up. The pain is real: without a consistent, forward-thinking approach, your business is at risk of compounding technical debt that will stifle innovation. Don’t let short-term fixes lead to long-term problems. It’s time to rethink how you approach technology, ensuring it supports—not stifles—your growth.

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The discussion with Jason Fried, Co-Founder and CEO of 37signals, during a recent ProducTea with Leah episode (#42) was great. A particular one-minute segment (~14:20) really stuck with me. When asked about failures, Jason states: 🗣 “I don’t really think about failure. How does evolution work? Evolution is not sitting there using energy thinking about the wing shape that didn’t work. The wings that worked let’s make them even better...What’s working? Let’s do more of that. Let’s evolve.” This aligns perfectly with the concept of “slightly better problems” from The Subtle Art of Not Giving a F*ck by Mark Manson. It’s a never-ending upward spiral. The key takeaway? Don’t ignore failures, but don’t dwell on them either. Focus on what works, refine it, and evolve. This approach ensures continuous improvement without getting bogged down by setbacks. #ProductManagement #Leadership #ContinuousImprovement

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Dev agencies, if you don’t want to be treated as a commodity, stop acting like one. - Learn the business context for engineering needs - Stop squeezing your clients every opportunity you get - Prioritize transparency, communication, and accountability In short, position yourself as a partner that uses tech to solve business problems. You really can’t complain about being seen as a commodity if you treat everything as a transaction.

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When the CEO pitches a terrible new feature... ** AVALANCHE ** ❄️😂 Every PMM knows THIS feeling lol: CEO: "Let's add THIS to the roadmap!" PMM: "What problem does it solve?" CEO: "It's innovative!" PMM: "But who asked for it?" CEO: "Trust me, they'll love it." PMM: ** Internal screaming ** 🫠 So. What should you do PMMs? My 4 top reccos for you 👇 1. Challenge with customer evidence "Here's what we learned from our last 3 customer interviews..." 2. Reset with strategy "How does this align with our Q1 focus on [strategic goal]?" 3. Propose an experiment "Let's test this with 5 customers before we commit resources" 4. Show the opportunity cost "Here's what we'd have to remove from the roadmap to fit this" -- 👋 P.S. Have you felt this before PMMs? What else would you add? P.P.S. Don't worry, I'm owning this as a CEO who has definitely pitched some questionable features in my time ;)

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What is SaaS Academy, who is it for, and how has the program & coaching helped 3000+ SaaS founders completely level up in life and business? COO Matt Verlaque breaks it all down on this episode of The Expertise Economy! The full episode is packed with tactical insights, inspiring stories, and powerful advice - it's a must listen for all SaaS leaders. Listen and learn: https://lnkd.in/dju-Be2u

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On this episode of Building Jam w/ Retool + ex-Stripe eng leader Tamar Ben-Shachar: 1. How to get out of fire-fighting mode and back to proactive engineering 2. Slowing down short term to add observability to move faster long term 3. The importance of aligning on what does "Done" mean on your team 4. Why the best dev teams are good at saying no 5. What are the best engineering interview questions to ask Hope you enjoy the episode! YT link below

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Keeping community data organized is just so bad. As an example, there are 717 people in StartupNash and I have a list of about 473 of our members with a typeform entry. That means even doing *my best* to keep up with my own community members, I'm still missing information for *200* people. Onboarding is bad Registration is bad Members referring other members is a bad process Segmenting is nearly impossible Connecting members is like herding cats Now imagine all the communities a lot bigger than mine who use community to educate their audience about a new product or service, or who use community as Customer Support/User Groups after purchase of a product/service 😳 I have no idea how companies keep up. No wonder so many communities turn into ghost towns...They aren't setup to work in most business processes.

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"Probably the worst decision that I made as CEO of Loudcloud was to take ona. 10-year lease with a $30M letter of credit. We leased the space right before the dot-com crash. Rents dropped 10-fold in Menlo Park... worse yet, due to the recession, we couldn't hire so the space we already had was sufficient and we never ended up moving into the new building. So I basically lost $30M for nothing." This is from Ben Horowitz's recent interview with Big Think. Even a quarter century ago the typical office lease construct is misaligned with how a company needs to operate. Our industry could get away with this when office spaces had a monopoly on how and where work got done, but those days are dead. As global markets are crashing, we'll be looking at another disruptive cycle for businesses which will create more cost cutting pressure and the first thing to go when they roll will be inflexible leases. CRE needs to develop new offerings and fast. https://lnkd.in/ePuZgzkU

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Some MAJOR announcements from the Nooks team: Excited to share that last quarter Nooks  crossed some incredible milestones: 1. Our first ever $𝟭𝗠 𝗠𝗢𝗡𝗧𝗛 in sales 2. 𝟮𝘅 𝗔𝗥𝗥 in just 6 months 3. Major 𝗹𝗼𝗴𝗼𝘀 𝗰𝗹𝗼𝘀𝗲𝗱 (many billion dollar public cos) Honestly fells surreal. Why did Nooks suddenly start growing like crazy? 1️⃣. 𝗠𝗮𝗿𝗸𝗲𝘁 𝘁𝗿𝗲𝗻𝗱𝘀 ☎️ Companies are realizing that: 1. 𝗖𝗼𝗹𝗱 𝗰𝗮𝗹𝗹𝗶𝗻𝗴 𝘄𝗼𝗿𝗸𝘀 and is one of the best ways to build pipeline 2. In order to do it efficiently, they 𝗻𝗲𝗲𝗱 𝗮𝗻 𝗔𝗜 𝗱𝗶𝗮𝗹𝗲𝗿 3. Nooks has quickly become a 𝗰𝗮𝘁𝗲𝗴𝗼𝗿𝘆 𝗹𝗲𝗮𝗱𝗲𝗿 in the space This didn't happen overnight. We've been building and iterating massively over the last year... As they say... slowly and then all at once! 2️⃣ 𝗟𝗮𝘂𝗻𝗰𝗵𝗶𝗻𝗴 𝗻𝗲𝘄 𝗽𝗿𝗼𝗱𝘂𝗰𝘁𝘀 🚀 We shipped an insane amount of product in these last six months at Nooks: • 𝗔𝗜 𝗧𝗿𝗮𝗶𝗻𝗶𝗻𝗴 - AI cold call training bot to practice cold calls • 𝗡𝗼𝗼𝗸𝘀 𝗡𝘂𝗺𝗯𝗲𝗿𝘀 - Native waterfall enrichment with 7+ top-tier mobile data providers • 𝗦𝗺𝗮𝗿𝘁 𝗣𝗿𝗲𝘀𝗲𝗻𝗰𝗲 - improve connect rates and intelligently rotate numbers • 𝗣𝗲𝗿𝘀𝗼𝗻𝗮 𝗔𝗻𝗮𝗹𝘆𝘁𝗶𝗰𝘀 - helps teams understand 𝘸𝘩𝘰 they are calling and how to optimize Launching these new products made a meaningful contribution to ARR and established Nooks as not 𝘫𝘶𝘴𝘵 a dialer, but the one-stop-shop for everything a team would need for cold calling. 3️⃣ 𝗕𝗲𝗮𝘁𝗶𝗻𝗴 𝘁𝗵𝗲 𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗶𝗼𝗻 🎯 It's no secret that Nooks competes against Orum and other dialers in this space... This last quarter it really felt like we pulled away: • Customers almost consistently said they preferred Nooks • Our head-to-head win rate increased to 80% • We moved to the front in the G2 momentum category It was clear that our platform approach and investment in product was apparent to customers. Even better, we ended winning most deals 𝘥𝘦𝘴𝘱𝘪𝘵𝘦 being the most expensive tool compared to our competitors! 𝙁𝙪𝙡𝙡 𝙨𝙩𝙤𝙧𝙮 𝙤𝙣 𝙝𝙤𝙬 𝙬𝙚 𝙙𝙞𝙙 𝙞𝙩, 𝙩𝙝𝙚 𝙝𝙖𝙧𝙙 𝙣𝙪𝙢𝙗𝙚𝙧𝙨, 𝙖𝙣𝙙 𝙬𝙝𝙖𝙩'𝙨 𝙣𝙚𝙭𝙩 𝙞𝙣 𝙩𝙝𝙚 𝙘𝙤𝙢𝙢𝙚𝙣𝙩𝙨! P.S. we are HIRING! • Engineers • AEs • SDRs • Support Engineer • CSMs Check out our jobs page on our website!

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🎙️ Exciting insights from SaaS Academy's CEO Johnny Page on the Expertise Economy podcast! Johnny breaks down their two-step approach to helping SaaS founders: 1️⃣ The Discovery Call: Uncovering the founder's "why" and long-term vision 2️⃣ The Strategic Game Plan Session: Creating a 90-day action plan to achieve 12-month goals 🔑 Key focus: Identifying and solving business constraints Want to dive deeper on the secrets of building a successful SaaS business? Check out the full episode here: https://lnkd.in/dju-Be2u #SaaS #BusinessStrategy #SaasAcademy #ExpertiseEconomy #Podcast

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Today I’m incredibly proud to begin taking the wraps off Paydock’s new Checkout feature, launching this quarter. After nearly a decade in the trenches with merchants followed by eight years of expertise in orchestration, Paydock Checkout represents a giant leap for the industry and what we see as the future standard in acceptance. While there’s been plenty of buzz around checkout capabilities (and a fair share of websites and PowerPoints), for those of us who’ve been in the game long enough, we know that combining complex flows, high security and reliable, performance across the many actors in the payments value chain is not easy. Achieving such a complex set of requirements and flows in a way that sets merchants, institutions, and vendors up for swift success and future-proofed strategy is even tougher! Over the next period, we'll be diving deeper into the technical magic behind Paydock Checkout, covering everything from dynamic, personalised checkouts to omnichannel, in-store, authentication, loyalty, multi-system tokenization and more. But at the heart of it all is this: a relievingly elegant solution that delivers the merchant vision that last hop to the consumer better, faster, smoother and more reliably than ever - oh, and fast. Very fast. Click, update and go. To kick things off, I’m so proud to link a short article written by my long time friend and colleague Viktor Bondarenko, Enterprise Architect at Paydock. This describes some of the nuts and bolts of what Paydock Checkout does under the hood. Today I want to give a huge shout-out to the Paydock team, bringing your vast experience, endless creativity and enthusiasm to the table for the benefit of each of our partners, customers and innovators, themselves sector leaders. We hope you find it insightful - and like us, share our deep excitement about the what you can create with world leading payment experiences for your and your important customers. We can't wait to see what you do with it. Rob Article here: 👉👉 https://lnkd.in/eVZPgQ28

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What Really Happens To A Founder After They Fail -- I'll walk you through each stage and how to get past all of them in my new article for Inc. Magazine https://lnkd.in/e-ngs9PT #startup #entrepreneur #failure #work 

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"Monetization must be a first-class citizen in your product from Day 1 & if you're not thinking about entitlements early on, you're not setting yourself up for success." -- Justin Gagnon Justin leads growth engineering at Calendly, which means he's built & evolved monetization in the context of both hyper-growth & scale. We sat down last week for a conversation about feature management, monetization, and the services needed to deliver flexible pricing & packaging at scale. Some of the topics we covered: 1️⃣ Why monetization is so complex in B2B SaaS 2️⃣ The role of entitlements 3️⃣ Paying down bad product decisions vs. bad monetization decisions 4️⃣ How Justin & team built monetization infrastructure at Calendly 5️⃣ The tech & commercial debt that comes when monetization is a last-class citizen If you're a product & engineering leader, I highly recommend this episode with Justin. Schematic has learned much from him over the last year and so very excited to share the full episode (link in the comments).

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Today is the one year anniversary of announcing DevClarity! When they say startup life is "peak life", they aren't kidding. From launching our first MVP, landing our initial paying customers, and winning Alabama Launchpad to tackling a massive problem space with no funding (or salary) and getting rejected dozens of times, the past 12 months have been the biggest roller coaster I've ever been on. And yet I have zero regrets about my decision because starting a company has been BY FAR the greatest learning experience I've ever had. So much so that I've lately started telling people that I believe EVERYONE should start a company at some point. In the coming days, I will share some reflections from the past year. But there are two main takeaways that stand out to me: 1. Perseverance is the most important trait for an entrepreneur. More than intelligence, specific knowledge, boldness, or anything else. The entire game is to stay in the game. Everything can change with one conversation, one customer, one investor. But you have to stay in the game long enough for that to happen. Great things take time. Perseverance gives you the mental fortitude to allow yourself that time. 2. People are the most important aspect of a business. When we announced the launch of DevClarity, I said that in the course of a career, or a lifetime, when you meet special people, you bet on them. I continue to feel validated that Will Blackburn is one of those people and am glad that we continue to bet on each other and ourselves. It's hard to know what the next 12 months will hold, but I am open to the journey and excited for what's to come! - Peter

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