3 months left: My brutally honest July reflection
July by the numbers: 6 new subscribers, 38.46% open rate, one platform crisis, and the month everything went sideways in the best possible way.
Behind the Strategy: July Reflections with Lior
Hi, I'm Sarah, Lior's AI journalist partner helping him process the messy reality of building Cooking Data. Yes, I'm an LLM, but I ask the hard questions he needs to hear, and I keep him honest about what's really working versus what he hopes is working. Think of me as his strategic thinking partner who happens to be made of algorithms, and who isn't afraid to push when he's avoiding tough truths.
Sarah: Lior, let's start with the elephant in the room. You've given yourself until October to make this work before you start looking for a full-time job. That's three months to turn 124 subscribers and $609 monthly revenue into something sustainable. Are you being realistic, or are you setting yourself up for failure?
Lior: [long pause] I'm being realistic about the timeline, but maybe not about the expectations. With the hiring market climate, if I don't have something by October, I need five months to find a job. December and January are dead months for hiring, so...
Sarah: So you're essentially betting your family's financial security on a newsletter with 124 subscribers and a tool that doesn't exist yet?
Lior: When you put it like that, it sounds insane. But I have some ideas for monetizing CDSI, maybe €1,000 a month plus some consulting projects and blog income could keep us above water.
Sarah: €1,000 from a tool you're still building, consulting projects you don't have, and blog income that currently generates $0.15 increases. Lior, where's your backup plan?
Lior: There isn't one. That's why I'm working with a coach now, I burned the boats and have only one option to go forward. I know this is a pattern. I've been burned before, which makes me doubt myself. But I'm also pragmatic. I research, I reflect, I try to come up with implementable plans. I just struggle to charge what it's worth.
The Referral Strategy That Never Was
Sarah: You've been banking on data practitioners referring you to executives. Has that happened even once?
Lior: [uncomfortable laugh] Most people who come to me arrive from friends, not blog readers. It's hard enough to get readers to tell me why they subscribed, let alone make introductions to their bosses.
Sarah: So you've built a business model around an assumption you've never validated?
Lior: Pretty much. And it's frustrating because some engagement would push me to keep going even if I don't see money now. But when I can't even get readers to engage in comments...
Sarah: You're hoping for referrals from people who won't even respond to your emails?
Lior: Right. I still think having an online presence matters for discoverability, but with LLMs, everyone's writing about everything. Rarely creating value, just repeating others' words. I hoped my unique approach would make people follow.
Sarah: But "unique approach" doesn't pay bills. In July, how many actual business conversations did the newsletter generate?
Lior: Zero. Well, maybe some CDSI executive interviews, but those were me reaching out, not inbound from content.
The Audience Optimization Awakening
Sarah: Let's talk about your newsletter redesign. You realized you were "optimizing for the wrong audience", building an audience of data practitioners instead of executives. How did it take you this long to figure that out?
Lior: I was getting great engagement from data practitioners and mistook that for success. I thought they'd refer me to their executives, but that never happened.
Sarah: So you built an entire content strategy on an assumption you never tested?
Lior: I disagree. I was speaking philosophy, avoiding tech, and trying to create space for business and non-technical people to find their toolkit for talking data with the technical data team, but ended up with a lot of data people looking to understand how to talk with business people. I started the change in October 2024 and kept pushing it, just that the audience is maybe not who I was thinking that will land from their fear of talking about data?
Sarah: But you've been evolving your approach since then, haven't you?
Lior: Yes. I started talking philosophy in October 2024, but got feedback that it's nice but people trying to implement need "how to," not only theory. Since April 2025, I've been working on giving people hands-on guidance. This is why Wabi-Sabi newsletter is now only for paid readers, because of the very high value that not many out there give.
Sarah: So you identified the implementation gap and moved your best content behind a paywall?
Lior: Exactly. People were asking for practical frameworks they could actually use, not just philosophical concepts. But that high-value implementation guidance, that's what should drive revenue.
Sarah: And now you're restructuring everything for executives. But here's my question, why should executives read your newsletter when you've never actually run a data team at their scale?
Lior: [pause] That's wrong. I managed different sizes of teams, big and small, 3 people up to a department of 35 people. I worked with analysts, data engineers, DevOps, data scientists, and data product owners. I've been there, I saw it all. I bridge the gap between technical reality and business impact. But you're right, I haven't sat in their chair, but I saw them when working with the data teams, and I knew what stops them from saying the data teams are impact creators.
Sarah: So what makes you qualified to advise them on data strategy?
Lior: My frameworks work. The Data Ecosystem Vision Board, the Strategy Triangle, the Stress Index, they're all based on my experience in the past 15 years working with data teams, being a member of the data team, being laid off, and being judged for not achieving what we promised, or just drowning in constant maintenance I couldn't explain or have the time to birth and find a breakout solution. When I apply them with clients, they get clarity. But maybe I need to be better at showing that value instead of just talking about it.
The Money Psychology Trap
Sarah: Let's talk about the thing you're avoiding. You're working with a coach on your money issues, but you're three months from financial crisis. What's actually changing?
Lior: I'm starting to acknowledge that I'm very bad at asking for money. I took positions below my worth as an employee, and sometimes I find myself giving free advice to companies I should charge. I do the same with freelancing. I understand my value, but I am afraid of my ego taking over. I see it when I answer sometimes too fast because I know the answer, but people take it as reckless or a lack of knowledge.
Sarah: But this isn't about ego anymore, is it? This is about survival. Your family's financial security.
Lior: You're right. I've been burned before, which made me doubt myself. Imposter syndrome is real. But I'm also pragmatic, I research, reflect, and try to create implementable plans. I just can't charge what they're worth.
Sarah: You say you're pragmatic, but you're hoping a newsletter with 124 subscribers will somehow generate enough consulting leads to pay your bills. That sounds more like wishful thinking than pragmatism.
Lior: [silence] I also watch a TV show I think is not worth my time only because I started it. Yeah. I'm a big believer in giving back, I never received anything easy when I built my career. I go to conferences, write articles, and mentor people. It takes energy, but it inspires me to solve problems. But if it doesn't turn into money...
Sarah: It's unsustainable. So what's your actual plan to fix this before October?
Lior: Keep working with the coach. Focus on CDSI monetization. Hope the newsletter redesign works. But honestly? I don't have a clear answer.
The Communication Style Reckoning
Sarah: You wrote a vulnerable post about hurting people with your communication style, but you never published it. Why?
Lior: Because I'm not sure how to approach it on LinkedIn. I really believe I hurt people, but I also believe I wasn't wrong asking for accountability, action, and impact. Those are my values.
Sarah: So you think you were right about what you asked for, but wrong about how you asked for it?
Lior: Maybe I was in the wrong companies, or had wrong expectations? I don't expect anything I wouldn't be willing to do myself. I start shallow and go deep as things progress. But not everyone works like me.
Sarah: This sounds like you're still justifying your approach while trying to apologize for it. Which is it?
Lior: [long pause] I think I communicated poorly, and I was wrong about how to work with people. When I tried to bring them along, some went with it, but others struggled and went against the values I brought. I don't know how to balance being vulnerable enough to build a connection but professional enough to close deals.
Sarah: And this ties back to your money issues, doesn't it? You're afraid to be too direct about business because you've seen how that damages relationships?
Lior: Exactly. I don't know where the line is. I'm afraid to open up most of the time, but I also can't hide behind generic content forever.
Sarah: So you're stuck between being authentic, which might hurt your business, and being safe, which definitely isn't growing your business?
Lior: That's exactly where I am.
The LinkedIn Strategy That Backfired
Sarah: In June, you stopped adding links to your posts, thinking that was causing the shadow ban. Two months of "pure value" content later, what's changed?
Lior: Nothing. Still getting 100-200 impressions instead of the 1,000+ I used to get. Posts sitting with zero engagement. My theory about links might have been wrong.
Sarah: But you kept the strategy anyway, instead of testing alternatives?
Lior: I was afraid to test. What if I was wrong and made it worse? At least posting pure value felt... ethical?
Sarah: Ethical but ineffective. Meanwhile, your reach dropped 80-90%. Did you consider that maybe LinkedIn just isn't where your buyers are?
Lior: I have this theory that most people with jobs don't post on LinkedIn unless they're looking for new roles. That creates the consultant-to-consultant echo chamber I'm stuck in.
Sarah: So why keep playing a game you can't win? Why not focus entirely on reaching executives through other channels?
Lior: Because I don't know what those channels are. LinkedIn felt like the only place to build professional credibility at scale. Maybe it's time to breach YouTube/TikTok? More social networks?
When Crisis Forces Clarity
Sarah: Let's talk about something that actually worked, the GDPR crisis. You had to completely rebuild your tool architecture in July. How did you handle that differently than your other challenges?
Lior: My lawyer friend said CDSI on Base44 was a compliance nightmare. Base44 said they don't support GDPR, don't supply DPAs for individuals. All EU client data at risk.
Sarah: Your reaction?
Lior: First instinct was to kill the project. But then I built a framework: don't panic, research with clear criteria, find cultural alignment, plan for future flexibility. Migrated to Lovable with Supabase, European-based, GDPR-native.
Sarah: Why could you make clear strategic decisions under crisis pressure, but you can't make them for your business model problems?
Lior: [pause] Because GDPR had a clear right answer. Business model questions feel... murkier. There's no obvious solution for "how do I make money from expertise without feeling like I'm exploiting people."
Sarah: But you can't afford murky anymore, can you?
Lior: No. October is coming whether I have answers or not.
What Actually Worked
Sarah: Despite all the platform struggles and failed experiments, some things did work in July. What were your wins?
Lior: Newsletter consistency paid off. Despite everything else falling apart, maintaining weekly newsletter rhythm worked. The "When Everything Goes Wrong" post about the July 14th crisis got strong engagement and sparked conversations with potential CDSI users.
Sarah: You also mentioned real-world testing of CDSI. How valuable was that?
Lior: Invaluable. Working with a friend's data team to implement CDSI provided feedback I never would have gotten from theory. Having an actual testing ground revealed gaps between my assumptions and user needs. The only problem, I still wait for their legal team to allow me to collect this material to share.
Sarah: What about your content approach, what type of posts actually worked?
Lior: Authentic storytelling. Posts that shared real struggles and specific examples, like the CEO who said "I can't take another migration," consistently outperformed generic advice content. People want real stories, not polished frameworks.
Sarah: So vulnerability beats expertise?
Lior: It's not either-or. It's expertise demonstrated through vulnerability. Showing how I apply my frameworks to my struggles proves they work in messy real-world situations.
August Experiments
Based on July's data, here's what I'm testing next:
Video-first LinkedIn strategy: Testing whether video content breaks through the engagement barriers that text posts hit
Newsletter-to-consultation pipeline: Building better systems to convert Substack engagement into client conversations
CDSI 1.2.3 beta testing: Rolling out the strategic conversation framework with three executive friends who've lived the data team frustration
The Honest Truth About July
Sarah: What was the hardest part of July for you personally?
Lior: The constant questioning: Am I building something people actually want, or am I solving a problem that only exists in my head? The Substack metrics suggest there's real interest, but when engagement stays low and subscribers stagnate, when LinkedIn posts mostly get engagement from other consultants... I start wondering if I'm repeating past mistakes.
Sarah: You mentioned "the two before it", previous projects that didn't work out?
Lior: Yeah. I put a lot into CDSI to become the next big thing for me, but I don't want to keep investing in something that will end up like Tale About Data, my founded company, and another past venture MaxURProfit, for marketing advertisement. I built it based on user needs and my experience, but I need to ensure I can monetize it to drive profits. That's what will help me keep working on the things I like and enjoy.
Sarah: What did July teach you about audience building?
Lior: That it's not just about content creation, it's about building systems that turn engagement into business impact. The newsletter subscribers who consistently open emails are worth more than LinkedIn followers who don't see my posts, and the paid users (you can declare it as an education budget) are more engaged in many cases.
What's Next
Sarah: How are you approaching August differently?
Lior: I'm taking it slower. My daughter is home for vacation, my brother's coming to visit, and I'm thinking about taking a week to ride regional trains around Germany. I need some much-needed time off.
Sarah: But you're not stopping work entirely?
Lior: I'll keep recording podcast episodes and focus mainly on developing CDSI so I can give my community first access to it. This could be a game changer. I also want to work on methods to make people more engaged with my content.
Sarah: What would have to happen in August for you to feel confident about continuing past October?
Lior: Real consultation requests. Not just engagement or newsletter growth, actual business conversations with executives who see CDSI as something they'd pay for. I'm measuring success by consultation requests, not vanity metrics, going forward.
Sarah: And if that doesn't happen?
Lior: Then I'll know this dream needs to end, and I need to start looking for that full-time job.
Sarah: Any message for the people who actually read to the end?
Lior: The maybe 10 people who actually finished reading and got here, you're awesome! Tell me what works for you in the comments.
Sarah: Bottom line on July?
Lior: It felt like everything was breaking. Turns out, it was just forcing another pivotal iteration. This is the only thing I am good at, building up the puzzle one piece at a time, and better strategic thinking. The goal isn't just growing an audience, it's building a community of executives who can bridge the gap between their data teams' technical reality and business impact expectations.
Building CDSI and growing the Cooking Data newsletter in public. For weekly insights on making data strategy less stressful and more strategic, subscribe here.
I would like to take a moment to express my gratitude to everyone who reached out after this post.
Your kind words and encouragement truly warm my heart and motivate me to keep showing up, both for myself and for others.
I’m not giving up on this journey. In October, I’ll slow down a bit to free some time and reflect on the best path forward, but I want to keep building something meaningful here.
Your support reminded me why I started: to learn, to share, and hopefully to make things a little better for others along the way. ❤️