Bobby Tahir @bscalable
4x CTO. 20+ years in tech. Sharing lessons from private equity, enterprise & startups. AI š¤ 1st, newsletter & podcast for CTOs, car guy & cat dad š± newsletter.technocratic.io For tech execs š Joined November 2011-
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One unfortunate truth about life: When youāre building a thing, people around you are generally attracted to your end success, not the long struggle. It can be your friends or even loved ones ā they just want to applaud the final result. You alone must deal with theā¦
All the times you thought everything was fucked and it all passed. And now you're on to a new set of problems; sitting there worrying. Meanwhile, life is slipping away.
Itās funny, in the early days of the Internet, we couldnāt stop giving it ridiculous names: - The Information Superhighway - The World Wide Web - And āCyberspaceā Like somehow the Internet wouldnāt work unless we named it just right. Fast forward to today and weāre doing theā¦
Building a business is harder than staying with a 9 to 5. Don't let people tell you otherwise. If it was easier everyone would be building a business. It's not just hard -- it's 5x harder than a day job. But the upside is 20X.
If AI makes coding faster it still hasnāt solved the bottleneck. The issue is product requirements. The right requirements, at the right time. Agree?
What's holding you back is not knowing what you want. You have goals but they may not be authentic. To really win you have to know what you want clearly and it has to be real & authentic. It can't be something you think you want, it has to be something you actually want.
Steve Jobs vs. Sam Altman Steve was a Marketer turned Technologist. Sam is a Technologist turned Marketer.
For those building companies -- yeah, it gets lonely. You make the hard calls. You absorb the chaos. You smile through the stress so your team doesnāt have to. Some days, no one gets it. Most days, no oneās coming to save you. And thatās the point. This is what makes buildingā¦
For CTOs: nobody calls the internet "just a tool". And AI? Same deal. This isn't Git 2.0. This isn't the next Cloud wave. This is 100x bigger. We're not optimizing, we're completely reinventing the SDLC. AI is the new foundation. Itās changing how we build software, how weā¦
A lot of developers are very happy right now that ChatGPT 5 wasn't anything revolutionary, so far...
AI is definitely changing the rules enterprise software UX. But it's not clear CONVERSATIONS are the answer. I don't want to have a discussion to get what I need. I simply want the AI to know me enough for the right information to appear. No convo, no clicks, no scrolling -ā¦
GPT-5 is out later today. So, same crappy results but just much, much faster?š All joking aside, will it have easy autonomous task execution? Will it be as big of a leap from 4 to 5 as it was from 3 to 4? What about price? Will we pay $200/month to get actual v5? Will itā¦
Private Equity likes to measure things...that's no secret. The right mindset to have as an exec is that this is FREEING. You donāt have to guess what matters anymore. And you donāt have to fight for attention when you do well. When everything is measured, clarity wins. Ifā¦
If AI agents become good enough in the near-term to accurately get work done for us, aren't we back to calling them products? And if AI agents eventually become as good as say, Data in Star Trek, then don't we need to treat them with sentient species status? Therefore, the nameā¦
The old school tech companies are failing with AI: - Microsoft CoPilot is an irritating joke to many developers - Meta is paying through the nose for AI engineers but output is unclear - Google Gemini is doing great technically but nobody seems to care - Amazon is a mishmash ofā¦
How do you avoid hiring the wrong CTO? After years of hiring for this position I have a few tips. First, keep in mind that hiring the right CTO isn't about finding the "best" oneāit's about finding the right fit for your companyās STAGE OF GROWTH. In a world filled with greatā¦
We're at the most innovative time in history and at the most dangerous. If we hand over too many critical global systems to AI too fast, we'll likely increase risk substantially. But we also need to keep technically innovating and moving the ball forward on new AI capabilities.ā¦
If you're a CTO or VPE a quiet Saturday morning is the perfect time to bone up on your financial game & acumen. And I've got the perfect guy to help you on this: @cjgustafson222 CJ is super insightful on everything finance and writes VERY practical content for technologyā¦
CTO should really stand for Chief Trouble Officer. They don't tell you this but everything that goes wrong in your company will fall on your head. One way or another CTOs get blamed for everything. - Sales issue? The product stinks. - HR can't hire? The tech team doesn't knowā¦
I came to find out that my former boss, actually my first boss, has passed away. He was only 48. His name was Paul and he ran IT for a large company back when that was a fun (ish) job. Paul was always laughing and joking but he could also be stern and assertive when needed. Iā¦

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