Christopher Nelson

Helping You Build Wealth with Tech Equity and become the Founder of Your Financial Independence

In the early 2000s,  my focus was on growing my skills, climbing the ladder, and being where I needed to be to get the job done. 

In 2009, I burned out hard. 

My new plan was to work for equity in tech start-ups and become financially independent.

Swing and Miss, the first start-up company I chose to work for, was going nowhere (equity worth zero). 

What happened? Did I screw up everything?

I chose the company because I was passionate about its mission, but I had not examined it further. I had no real plan.

My next step was to call people that I knew had been successful in working for equity in tech and see what was different in their "playbook."

Key lessons learned after first dead-end tech startup:
 -In trading my time and talent for equity, I need to think like an investor
 -Create a rigorous due diligence process
 -Don't fear failure, stay in the game
 -Keep learning

May 2011, Started at Splunk Pre-IPO

April 19th, 2012 Splunk had a break-out IPO

April 20th, 2012 feelings of anxiety and fear creep in about how to manage the newly generated wealth. 

I had to figure out how to get real income (real estate) into my portfolio. I needed something sending me checks.

Key lessons learned after the first IPO:
 -How to invest in private equity real estate
 -Set up my family for generational wealth
 -Own the result (don't put my future in someone else's hands)

New Mission: Be the Founder of a Micro Family Office to become Financially Independent.

Strategy:
 -Live within paychecks
 -Bonuses for extras
 -Invest all of our equity

I climbed the ladder to become a CIO. 

At the peak, I realized I wanted to build my DIY Family Office more than climb the ladder.

I changed roles and reduced my scope. 

On August 26, 2022, I graduated from my W-2 job to live a lifestyle by design.

I founded WealthOps in 2023 to equip technology professionals with the skills to build and run their portfolios.

My Portfolio:
 -3  Start-Ups I worked for IPOed (SPLK, YEXT, GTLB) <-Traded Time
 -Replaced paycheck with $200k+ of portfolio income
 -Built my Micro Family Office
 -Running a company structured around my life

My Results:
 -Highly Diversified Portfolio - Stocks, PE Real Estate, Debt, Businesses, and VC. 
 -$223 Million AUM with investors
 -7 Investments  gone full cycle with an Avg 19.4% IRR to investors
 -1000+ tech employees being educated on Managing Tech Millions
 -20+  and growing Portfolio CEOs

My mission - 1000+ Portfolio CEOs

Learn more about how I did this, join our free live workshop  →  https://dub.sh/wealthops-linkedin

Founder

Tech Careers and Money { }, a media and education company whose mission is to elevate Tech Professionals' finance knowledge through unmatched and unbiased education in career and personal finance to equip them to make their best decisions. 


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We just crossed 100 members in 𝗧𝗵𝗲 𝗠𝗶𝗰𝗿𝗼 𝗙𝗮𝗺𝗶𝗹𝘆 𝗢𝗳𝗳𝗶𝗰𝗲 𝗔𝗰𝗰𝗲𝗹𝗲𝗿𝗮𝘁𝗼𝗿.

But here's what matters more than the number.

100 entrepreneurs, physicians, and tech professionals who stopped being clients and started being CEOs of their wealth.

Most wealth management sells you dependency. 
Hire us. Trust us. Let "us" handle it.

We teach the opposite.

You already run complex operations. 
You make million-dollar decisions. 
You manage teams and P&Ls.

The skills you used to build wealth? 𝘛𝘩𝘰𝘴𝘦 𝘴𝘢𝘮𝘦 𝘴𝘬𝘪𝘭𝘭𝘴 𝘮𝘢𝘯𝘢𝘨𝘦 𝘸𝘦𝘢𝘭𝘵𝘩.

You don't need someone to do it for you. You need the frameworks specific to wealth operations.

That's the shift these 100 families made.

They're learning:

- The Evergreen Portfolio Model.
- Structured Alpha Strategies.
- Asset Protection Strategies.
- Family Office Operations.
- The Deduction Stack. 
- The Income Pyramid.
- Entity Architecture.
- Tax Optimization. 
- Deal Evaluation.

Not theory. Actual implementation.

Same rigor you'd bring to building a product. 
Same systematic thinking you'd apply to scaling a business.

Just applied to the thing that ACTUALLY compounds over generations.

The difference between a client and a Portfolio CEO? 
Clients delegate and hope. 
Portfolio CEOs architect and operate.

In a few days, I'm hosting a live workshop on how to architect your own Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

Here's what attendees from last month's workshop said about it:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.
- 𝘔𝘢𝘶𝘳𝘪𝘤𝘪𝘰 𝘏.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.
- 𝘊𝘩𝘳𝘪𝘴𝘵𝘺 𝘞.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.
- 𝘗𝘢𝘴𝘤𝘢𝘭 𝘞.

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Tech Careers & Money Talk

𝗪𝗮𝗻𝘁 𝘁𝗼 𝗮𝗰𝗰𝗲𝗹𝗲𝗿𝗮𝘁𝗲 𝘆𝗼𝘂𝗿 𝗙𝗶𝗻𝗮𝗻𝗰𝗶𝗮𝗹 𝗜𝗻𝗱𝗲𝗽𝗲𝗻𝗱𝗲𝗻𝗰𝗲?💸

Join here 👉 techcareersandmoneytalk.com

Tweet Follow-up

Even Justin Welsh chimed in: https://twitter.com/thejustinwelsh/status/1628168298947919878?s=20

Post Follow Up

On the off chance you *do* want financial freedom — do these 11 things instead. 👇

- Ignore the above
- Buy back your time
- Start investing today
- Build a simple budget
- Learn personal finance
- Destroy credit card debt
- Work for equity AND salary
- Diversify w/ passive income
- Align your finances with goals
- Build a team of financial experts
- Join techcareersandmoneytalk.com

What did I miss?

50 - 50 Link

🧠 - Bonus Tip:  For Monday - Do A Brain Dump to Prevent Overwhelm 

Monday means mental overwhelm for Many. 

Objects in your head can be more stressful than they appear! 

Take piece of paper, 10 min and write down all the things you need to get done, work, life etc. 

Once you see them written down identify 3 things that have to get done today. 

Get to your base! 

TCMT Pod Page

𝗟𝗶𝘀𝘁𝗲𝗻 + 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗠𝘆 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 👇

🎧 Tech Careers & Money Talk 💸

www.podpage.com/tech-careers-and-money-talk-1/

TC&MN

Elevate your tech career and personal finance savvy.    

https://www.techcareersandmoneynews.com

Anti-Goals

Steal my Blueprint

Update Process

Actionable tips for growing your career, building wealth and living a life of impact. 
Always 3 minutes or less.

https://www.techcareersandmoneynews.com/

Find Rest 

🧠 - Bonus Tip:  Your Momentum is Fuel for your Mentors.  As your mentor sees you taking their input and iterating, they will be excited and want to participate more.  

Momentum breeds momentum.   

Hindi Video

Want all the details?   

Check out my origin story here on Audio : https://bit.ly/cnoriginstory

Watch it on YouTube! : https://youtu.be/7Hw-Y2hDtF8


From Equity to Exit 

Momentum for Mentors

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tech-careers-and-money-talk

careercadre

I Run My Own Micro Family Office and Teach Others to Do the Same | Founder @ WealthOps

In 2012, I became a millionaire.

Three months later, I realized I had no idea what to do with the money.

I met with wealth advisors. Every single one gave me the same pitch:

"𝘎𝘪𝘷𝘦 𝘶𝘴 𝘺𝘰𝘶𝘳 𝘮𝘰𝘯𝘦𝘺. 𝘞𝘦'𝘭𝘭 𝘥𝘪𝘷𝘦𝘳𝘴𝘪𝘧𝘺 𝘪𝘵. 𝘛𝘳𝘶𝘴𝘵 𝘶𝘴."

- Zero customization. 
- Zero long-term strategy. 
- Just a cookie-cutter portfolio.

That's when I discovered the problem:

If you have $1M-$30M, you're stuck in what I call the financial service desert.

You're too wealthy for mass-market advisors.

But not wealthy enough for a traditional family office ($100M+ minimum).

So I spent years studying how ultra-wealthy families actually manage money.

And I built what I now call a 𝗠𝗶𝗰𝗿𝗼 𝗙𝗮𝗺𝗶𝗹𝘆 𝗢𝗳𝗳𝗶𝗰𝗲.

The result after 4.5 years:
→ Portfolio generating $200K+ of annual cashflow
→ Principal still growing (not selling any assets)
→ 10 hours/week managing everything
→ Full control over every decision

Here's what most people get wrong:

They think wealth management is about picking stocks.

It's not. (This stuff comes last)

𝗜𝘁'𝘀 𝗮𝗯𝗼𝘂𝘁 𝗯𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗮 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘁𝗵𝗮𝘁 𝗼𝗽𝗲𝗿𝗮𝘁𝗲𝘀 𝘄𝗶𝘁𝗵 𝗼𝗿 𝘄𝗶𝘁𝗵𝗼𝘂𝘁 𝘆𝗼𝘂.

Here are the four-phases of every Micro Family Office:

𝗔𝗿𝗰𝗵𝗶𝘁𝗲𝗰𝘁 → Define your legacy and investment thesis
𝗕𝘂𝗶𝗹𝗱 → Create legal structures and assemble your team
𝗥𝘂𝗻 → Operate with monthly/quarterly rhythms
𝗦𝘂𝗰𝗰𝗲𝘀𝘀𝗶𝗼𝗻 → Transfer systems, not just assets

Look... if you're sitting on $1M+ and still treating your portfolio like a savings account, you're leaving money on the table.

Want to build your own Micro Family Office?

I'm running a free 2-hour workshop where I'll walk you through building the foundation - your Legacy Statement and Investment Thesis.

Over 1,000 people have attended so far.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

---

Here is what attendees from last months workshop said about it:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨𝘴 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.

- 𝗠𝗮𝘂𝗿í𝗰𝗶𝗼 𝗛.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.

- 𝗖𝗵𝗿𝗶𝘀𝘁𝘆 𝗪.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.

- 𝗣𝗮𝘀𝗰𝗮𝗹 𝗪.

Goldman Sachs just surveyed 245 families managing $1 billion+ portfolios.

Here's what they're doing while everyone else is paralyzed...

Despite big concerns, they're not sitting on cash.

They're executing.

The data tells a clear story:
→ 34%  are reducing cash positions
→ 39%  increasing private equity allocations
→ 38%  adding to their public equities
→ 26%  expanding private credit exposure

Here's what this actually means...

These families aren't reacting to headlines.

And the most important finding?

70% manage their investments in-house.

They're not outsourcing critical decisions to advisors.

They have clear investment theses.

They run quarterly reviews.

They make annual business plans for their portfolios.

This creates a playbook:
✓ Patient capital with decade+ time horizons
✓ Opportunistic deployment during dislocations
✓ Programmatic commitments regardless of sentiment
✓ Zero emotional reaction to geopolitical noise

The difference isn't wealth.

It's operational structure.

It's having systems that work when markets don't.

It's knowing what to do before you need to do it.

Most people with $1-30M don't have this.

They have... 
- Scattered accounts.
- Generic advice.
- No investment thesis.
- No operating rhythm.

The good news is this is fixable.

If you want to learn how to build these operational systems for your portfolio - the same frameworks these ultra-wealthy families use - I'm running a live workshop walking through the exact architecture.

Comment "WORKSHOP" and I'll send you the details.

Goldman Sachs surveyed 245 family offices managing $1B+ each.

Here's some takeaways from the data...

- 86% have AI exposure.
But here's what matters: 87% are also using AI to manage their portfolios. They're not just betting on the trend, they're operationalizing it in their own wealth mgmt.

- 72% are active in secondaries.
This isn't random. When there is liquidity pressure, family offices buy discounted assets. They have patient capital. No quarterly redemptions. No exit timelines forcing their hand.

- 33% now hold crypto (up from 26% in 2023).
Still a minority. Still selective but growing steadily. APAC shows the strongest interest - likely because they're most concerned about geopolitics (75%) and see digital assets as a hedge.

- 58% expect to be overweight tech in the next 12 months.
Despite market volatility. Despite valuation concerns. They're leaning INTO trends, not away from them.

Some regional differences...

- Americas: Highest PE allocation (25%) and increasing

- APAC: Most geopolitically concerned, highest crypto interest

- EMEA: New interest in hedge funds for sophisticated downside protection

If you want to learn how to build the operational structure these families use - adapted for $1-30M portfolios - I'm running a free workshop walking through the complete framework.

Tuesday, January 21st at 8:00pm ET.

Comment "WORKSHOP" and I'll send you the registration link.

Have over $10M in income? Your audit risk jumps to 8.8%. (𝟮𝟮𝘅 𝗮𝘃𝗴)

But here's what really caught my attention when I was digging through IRS data last week:

If you have over $20M in assets? 

𝗬𝗼𝘂𝗿 𝗮𝘂𝗱𝗶𝘁 𝗿𝗶𝘀𝗸 𝘀𝗸𝘆𝗿𝗼𝗰𝗸𝗲𝘁𝘀 𝘁𝗼 𝟭𝟴.𝟮%.

That's not a typo. Nearly 1 in 5 chance.

In 2024 alone there were $84.1 billion in penalties assessed.

Here's the thing most people don't realize:

The root cause of an IRS penalty often isn’t an error on your tax return.

It’s the byproduct of operating your wealth like a hobby, not a business.

- Improper entity structures. 
- Lack of documentation.
- Everything scattered.
- No routine systems.

𝗧𝗵𝗲 𝘂𝗹𝘁𝗿𝗮-𝘄𝗲𝗮𝗹𝘁𝗵𝘆 𝗱𝗼𝗻'𝘁 𝘄𝗶𝗻𝗴 𝗶𝘁.

They run Family Offices with clear governance, documented strategies, and institutional-grade documentation.

But you don't need $100M to operate this way.

You just need the right framework.

And that's exactly what a Micro Family Office does.

It gives you the structure, systems, and documentation that transform your wealth from a compliance risk into a well-run operation.

Because when you operate your wealth like a business, you're not just protecting yourself.

You're building something that actually scales and can be passed down.

Ready to get organized and stop flying blind?

Join my free live workshop on Feb. 4th at 8:00pm ET where I'll walk you through how to build your own Micro Family Office.

𝗬𝗼𝘂 𝗰𝗮𝗻 𝗿𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://dub.sh/mN0g8tK

---

Here is what attendees from last months workshop said about it:

𝘐𝘵 𝘸𝘢𝘴 𝘳𝘦𝘢𝘭𝘭𝘺 𝘴𝘵𝘳𝘢𝘯𝘨𝘦 𝘵𝘰 𝘧𝘪𝘯𝘥 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯 𝘵𝘰 𝘥𝘰 𝘵𝘩𝘪𝘴. 𝘐𝘵'𝘴 𝘵𝘩𝘦 𝘧𝘪𝘳𝘴𝘵 𝘵𝘶𝘵𝘰𝘳𝘪𝘢𝘭 𝘐 𝘤𝘢𝘯 𝘵𝘩𝘪𝘯𝘬 𝘰𝘧 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘴𝘢𝘺𝘪𝘯𝘨𝘴 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘶𝘴𝘦𝘧𝘶𝘭 𝘢𝘯𝘥 𝘶𝘯𝘣𝘦𝘭𝘪𝘦𝘷𝘢𝘣𝘭𝘦.

- 𝗠𝗮𝘂𝗿í𝗰𝗶𝗼 𝗛.

𝘠𝘰𝘶 𝘫𝘶𝘴𝘵 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘧𝘳𝘢𝘮𝘦𝘸𝘰𝘳𝘬 𝘵𝘩𝘢𝘵 𝘐 𝘸𝘢𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨, 𝘢𝘯𝘥 𝘐 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘢𝘵 𝘐 𝘯𝘦𝘦𝘥𝘦𝘥.

- 𝗖𝗵𝗿𝗶𝘀𝘁𝘆 𝗪.

𝘐 𝘵𝘩𝘰𝘶𝘨𝘩𝘵 𝘵𝘩𝘢𝘵 𝘸𝘢𝘴 𝘨𝘳𝘦𝘢𝘵. 𝘈𝘯𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵'𝘴 𝘴𝘰 𝘧𝘶𝘯𝘯𝘺 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘰 𝘮𝘦, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘱𝘳𝘦𝘴𝘦𝘯𝘵𝘢𝘵𝘪𝘰𝘯 𝘭𝘪𝘬𝘦 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰.

- 𝗣𝗮𝘀𝗰𝗮𝗹 𝗪.

You have to put $50,000 in one of these. Which are you picking?

Which of these metals do you think will have the biggest run up in 2026?

Cosmo Tech | The Decision Twin Platform for Supply Chain, Finance & Asset Leaders at Fortune 500 Scale | Simulate Tomorrow. Decide Today.

I specialize in the messy middle of B2B SaaS scaling—taking companies from erratic growth to a disciplined, high-performance revenue engine.

Most sales teams don’t fail because they lack talent; they fail because of ambiguity.
When forecasts can’t be trusted, pipelines move only through founder heroics, and managers report activity instead of owning outcomes, you don’t need another playbook—you need an operating system.

My operating philosophy: Cadence | Ownership | Process

I install a repeatable flywheel of operational excellence:

Cadence
A rigorous Rhythm of Business—daily, weekly, and monthly operating cadence that surfaces execution risk early, before it becomes a board-level surprise.

Ownership
Managers own outcomes, not just activity. Forecasts are built bottom-up so leadership can commit without caveats.

Process
Qualification and execution are standardized before adding headcount, ensuring hiring is tied to capacity and real revenue impact—not hope.

The proof (Ekahau — SVP, Global Sales, 2019–2024)
	•	Revenue: Scaled $25M → $65M ARR in five years
	•	EBITDA: Increased $7M → $32M (margins ~20% → ~50%)
	•	Team: Built a 130-person global organization while reducing per-employee cost 25%

Selected wins
	•	Healthentic: Doubled ACV ($5M → $10M) and drove 10× pipeline growth through GTM transformation
	•	ControlCase: Delivered 34% YoY growth and 300% expansion revenue growth

Currently

Available for VP of Sales or Fractional GTM leadership with B2B SaaS companies $5M–$30M ARR. I also lead SalesGSS (revenue operating frameworks) and DigitalRegIntel (regulatory intelligence for AI/fintech).

The Senator perspective

Two terms as a Washington State Senator taught me the value of high-stakes negotiation and public accountability. I bring that same discipline to sales: clear ownership and execution when the pressure is real.

“Steve is ‘Instant Offense’ for sales—rare and valuable. World-class at creating strategic, data-driven sales teams.”
— Jeff O’Mara, CEO (Healthentic) / GM (Ekahau)

Steve Litzow

AI didn’t kill sales reps.
It killed excuses.

In 2026, AI isn’t a productivity tool — it’s a truth serum.

It exposes:
• Broken process
• Weak management
• Fake activity dressed up as “effort”

If your sales motion is tight, AI compresses time-to-decision.
If it’s sloppy, AI just produces more noise — faster.

Most $10M–$50M ARR teams are about to learn this the hard way.

This is Week 1 of the SalesGSS 2026 Operating Series.
Eight weeks. Eight uncomfortable truths.

AI didn’t come for your reps.
It came for your excuses.

Comment “2026” if you want the series.

VP of Sales / Fractional VP (B2B SaaS, VC & PE-backed) for $5M–$30M B2B SaaS | Scaled $25M → $65M ARR | SalesGSS

Your closers aren’t the problem.
Your committee is.

Roughly half of qualified B2B deals don’t lose.
They stall.
“No decision.”

At $10M–$50M ARR, the pattern is consistent:
• Strong champion
• Positive calls
• Deal “feels good”

But it’s single-threaded.

One relationship trying to carry internal selling across:
Finance. IT. Security. Procurement. Operations.

The closer is persuasive.
The organization isn’t aligned.

With 10+ stakeholders involved, persuasion no longer scales.

Elite closers in 2026 aren’t smoother.
They’re better at internal selling.

They multi-thread early.
They equip champions.
They sell the decision process.

Quick diagnostic:

Can your reps name five stakeholders—and each one’s priority—in their top deals?

If not, you’re optimized for persuasion when you need consensus.

Week 2 of the SalesGSS 2026 Operating Series.
(Week 1: AI doesn’t fix execution—it exposes it.)

Comment “2026” if you want the series.

If you can’t prove value in the first 60 days, you don’t have a deal.

In 2026, long sales cycles aren’t what kill deals.

Delayed proof does.

Buyers will wait longer to buy —
but they won’t wait longer to know if they made the right decision.

57% of B2B buyers expect positive ROI within 3 months — not at renewal.

If a champion can’t point to a concrete win inside 60 days:

Confidence erodes
Finance steps in
“Commit” turns into “let’s wait and see”

That’s why the strongest teams aren’t closing faster.

They’re proving faster.

They define Day-60 success before the contract is signed.
They scope for proof, not size.
They treat time-to-value as a deal quality metric, not a CS problem.

If value only shows up at renewal, the deal was insured by hope — not evidence.

This is Week 3 of the SalesGSS 2026 Operating Series.
Next week: why slow product cadence is becoming a silent deal-killer.

This week’s regulatory signal isn’t clarity — it’s formation.

In the U.S., digital asset market structure legislation stalled again. In the EU, regulators are already questioning AI Act transparency practices well ahead of enforcement.

Different jurisdictions. Different tools. Same supervisory pattern.

Expectations are forming before rules finalize — and long before penalties appear.

That’s what shows up later in:
- Board and audit committee questions
- nvestor and acquirer diligence
- Bank and payment-partner reviews

Not “what did the law eventually say?”
But “what did leadership understand and monitor as expectations evolved?”

I publish a short Digital Regulatory Intelligence brief each Tuesday that documents these early supervisory signals — not predictions, not legal conclusions — just what’s forming in real time.

Most regulatory risk doesn’t show up as a rule violation.

It shows up later as a question regulators now ask routinely in enforcement actions:

“When did you become aware of this risk?”

Across new digital regulations and recent enforcement matters, regulators have shifted from checklist compliance to supervisory posture — an expectation of continuous, documented awareness.

Exposure today isn’t just what you did.
It’s what you reasonably knew — and when you knew it.

That’s why this is increasingly a board-level issue, not a compliance exercise.

Curious how others are documenting supervisory awareness before it’s asked for.

When supervision exists only in email, it doesn’t exist at all.

This week didn’t bring a sweeping new regulation.
That’s exactly the risk.

Across the U.S. and EU, regulators continued applying existing authority while legislative clarity remains unresolved. That combination — active enforcement discretion + unresolved rules — is where most future compliance failures are born.

Fast-forward 24–36 months and the question won’t be:

“Was the guidance clear?”

It will be:
“What did you know — when did you know it — and how was that knowledge supervised?”

This week alone:

SEC and CFTC signaled regulatory coordination is moving forward without Congress
EU AI Act transparency expectations quietly locked in
FinCEN delayed rules while Treasury intensified enforcement
Enforcement volume dropped — but guidance-based expectations accelerated

None of this required a new rule. All of it creates exposure.

If your supervisory awareness lives in emails, Slack threads, or people’s heads, it won’t survive diligence, exams, or enforcement.

That’s why we published this week’s DigitalRegIntel Supervisory Brief — and why we believe supervisory awareness needs a system of record, not a newsletter.

Because when the question comes,
explanations don’t count. Records do.

This week’s brief formally documents each supervisory signal referenced above.

#RegulatoryCompliance #DigitalAssets #AIGovernance #RegTech #Compliance

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