🎯 Mark Freeman II

onthemarkdata.com | Senior data engineer helping brands with GTM and content strategy.

I'm a community health advocate turned data engineer interested in the intersection of social impact, business, and technology. My life’s mission is to improve the well-being of as many people as possible through data—especially among those marginalized.
 
As the founder of On the Mark Data, I use this platform to help brands connect to data professionals through captivating content.
 
I received my M.S. from the Stanford School of Medicine and I'm also certified in Entrepreneurship and Innovation from the Stanford Graduate School of Business. In addition, I have worked within numerous startups where I have put machine learning models into production, integrated data analytics into products, and led migrations to improve data infrastructure.
 
The culmination of my technical skills, content success, and experience within startups would make me an asset whether you are looking to create a successful content strategy, engage in influencer marketing campaigns, or develop a go-to-market strategy for your startup.

You can learn more about opportunities to collaborate, my media appearances, or my content at onthemarkdata.com.

Tech Lead, GTM Engineering

• Joined as employee one to lead GTM at Gable to help us reach our first customers.
• Worked with the CEO to establish our GTM strategy, content strategy, and messaging for technical audiences.
• Building internal data products to drive our GTM strategy and sales.

Vin Vashishta

AI Strategist | Monetizing Data & AI For The Global 2K Since 2012 | 3X Founder | Best-Selling Author

I have helped over 9,000 senior++ ICs and executive leaders advance and stay relevant with high-end AI capabilities. Courses & Certifications: https://datascience.vin

Upskill your workforce to be AI-ready in 3 months: seminars@v2ds.com

Conference talks, brand partnerships, and thought leadership: partnerships@vinvashishta.com

Over 85% of AI projects fail to deliver a return on investment because they start with technology, not a business problem. I’m fixing that by empowering companies and training people to stop experimenting with AI and start monetizing it.

Define, align, and manage the business and technical transformations that turn C-level AI visions into products, productivity, and revenue. Since 2012, V Squared AI has worked with large enterprises to deliver over $4 billion in value.

My frameworks are built from working in the trenches. My practitioner-to-strategist journey allows me to bridge the critical gap between technical teams and the boardroom, ensuring that AI initiatives are not only technically sound but also commercially viable.

Partners & Disclosures: Dell Pro Precision Ambassador, NVIDIA Partner, & Gartner Ambassador.

Speaker’s Bio:

Vin Vashishta is an award-winning AI thought leader, best-selling author of ‘From Data to Profit,’ 3X founder with a successful exit, and CEO of V Squared AI, one of the first pure play data and AI consulting firms. The Wall Street Journal, Fast Company, and The Information have showcased Vin’s AI expertise.

He brings 30 years of experience in leadership, technical strategy, and hands-on technical product delivery. He has trained, productized, and monetized information and AI for 15 years and previously worked in software engineering and organizational leadership roles.

Founder & AI Advisor

Go with experience and a track record of success. V Squared is one of the oldest data and AI consulting companies in the world. Since 2012, that singular focus has built deep expertise in monetizing data, analytics, and AI.

V Squared's AI advisory services give clients clarity into the complete data and AI monetization journey. They trust us to implement frameworks that facilitate and streamline the journey. We provide expertise to remove roadblocks and avoid setbacks.

Our past and present clients include Airbus, Siemens, Walmart, JPMC, and over 20 SMEs.

Reach out for help with:
AI Product Strategy and Delivery
AI Strategy
Data & AI Organization Building and Scaling
Product Evangelization and Positioning

email: info@v2ds.com or DM me for more information.

Block laid off 40% of its workforce because Jack Dorsey finally realized it's a legacy middleware SaaS company, and he does not know how to survive the next 3 years. Here's the real AI story.

Block had 3,800 employees in 2019. It hired like a pandemic-era SaaS company chasing growth metrics. Headcount ballooned to 10,000. The stock dropped 75% over 5 years, and Dorsey only sees one way forward.

He is cutting 4,000 people and calling it an AI transformation, but Wall Street knows the real story. Dorsey has given up and is preparing the company to be acquired. The stock jumped 24% overnight.

Block processes payments and takes a cut. It is outdated middleware facing emerging AI platform business models. To survive, Block must use AI to grow the ecosystem or make it more efficient.

Dorsey does not know how to do either one, so he is backing out altogether and begging for a buyout.

Square Capital is a merchant cash advance that looks at transaction volume and fronts a percentage. Any bank looking at deposit flows has the same data. The opportunity used to be too small to be worth the engineering cost.

But AI tools change that and eliminate the cost barriers. What is Block's moat now? Distribution and habit will not be enough, and Dorsey knows it. Businesses, especially small businesses, optimize for price.

Block is a payments processor competing on price against Stripe and Adyen. It is a lender competing against bigger banks that realize they can underwrite small loans from their own data whenever they need a growth spurt.

Block is a legacy neobank that will soon compete with a wave of AI-first neobanks and incumbents who are transforming with a better vision of how AI platforms are monetized.

Block is a SaaS company in a race to the bottom that will soon be seen as bloatware. That's why Dorsey didn't cut gradually. He cut 40% in one shot and raised the 2026 outlook.

He made the company look lean and profitable overnight and is dressing up his company for a sale before the rest of the market figures out the obvious.

The AI age rewards two kinds of ecosystem or platform business models:

Those that grow the pie or ecosystem and monetize the growth.
Those that make the ecosystem more efficient or reduce risk and take a cut of the optimization.

Block does neither. It sits in the middle and takes a cut, relying on complexity and cost to maintain its position. What Block is about to realize is that AI also reduces the value of acquiring vs building.

The value proposition in acquiring used to be a 2-3 year head start. Now it is more like 6-12 months. I wish Dorsey and the remaining staff at Block all the best, but the future does not look bright.

And this narrative about AI replacing people is overblown. Growing businesses need people more than ever. Shrinking businesses try to paint over a lack of vision with AI hype.

Vendors spent years selling the data cloud built for analytics, and they think slapping “AI-Ready” on the same old architecture will do the trick. AI layers and semantic layers are mostly rebranded SQL engines and data catalogs.

SELECT *
FROM dataPlatforms
WHERE marketing = 'Hype'
AND reality <> 'Revenue';

The tape has tape on it at this point. Most businesses just finished ‘modernizing’ their data infrastructure, only to find out that in the time it took to modernize, that infrastructure became obsolete.

Executive leaders are realizing that they spent all that money and went through all that pain to upgrade to a platform that was modern 5 years ago. It does not support AI or agents, even though it has the ‘AI-Ready’ stamp.

C-level leaders just opened their wallets, and the business just finished a year-long migration. The paint is barely dry, and no one wants to talk about doing it all over again.

But the sweet, sweet AI ROI will not flow until they do.

I talk about Continuous Transformation because that is the new business reality. Technology is never done, so every architectural component must transform to keep pace. It is not enough to look at what the platform does today.

Will the vendor’s roadmap keep it current for the next 5 years so the business can generate positive returns?

Answering that question requires the business to define what it plans to build for the next 3-5 years. However, the business is waiting on the technology side to explain what comes next, so they know what is possible.

It is yet another example of what happens in businesses that have a Missing Middle. Technical strategy and platform roadmaps must be forward-looking and prescriptive.

Both must be built from opportunity discovery that is driven by pragmatic futurism, not hype cycles. Missing Middle roles (AI Strategist, AI Product Managers, and Strategic Technical Leaders) fill the gap.

Hire them or enjoy your tape salad.

taplio

The Battle

🎯 Mark Freeman II

Vin Vashishta

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taplio

The Battle

🎯 Mark Freeman II

Vin Vashishta

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Vin Vashishta's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreVin Vashishta's LinkedIn Performance