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Just now
I’ve been following the recent discussions around how hospital-affiliated contractual structures are contributing to burnout among early-career physicians. In a city as expensive as Manhattan, that mismatch between your responsibility and your actual take-home pay can really derail your long-term goals. I’d like to share some specific ways to audit your current agreement to ensure you're actually building personal wealth while you focus on your patients.
Most planning conversations with physicians start with generic asset allocation. For your stage, the bigger levers are cash-flow management, debt restructuring, and negotiating employment contracts that actually protect your long-term financial health — happy to walk through how we audit those three.
— Pivots away from generic advice toward the contract mechanics this audience is reading about.
With pending home sales slipping and Manhattan's luxury-to-typical price ratio where it is, a lot of your peers are re-running the rent-vs-own math. We're framing it around liquidity needs rather than long-term real-estate lock-in — I can share the model we use.
— Anchored to this week's housing signals for this exact audience.
2d ago
Given the recent discussions around potential IPO liquidity for the local AI sector, many developers are weighing whether to anchor their wealth in San Francisco real estate now or wait for more market clarity. We’ve been helping clients map out the tax implications of these equity events before they decide on a property purchase. I’d be happy to share a brief look at how we’re structuring those scenarios for your peer group.
5h ago
I've been looking at how the recent tariff refunds are impacting balance sheets for local business owners. Many of your peers are using this cash cushion to offset commodity inflation, but it's also a rare chance to clean up personal liquidity before any potential exit. Are you treating this as operating runway, or a bridge to your next chapter?
— Operational reality meets long-term exit strategy.
We've seen a few clients lately grapple with the 'identity shift' that comes once the daily grind of running the company stops. Financial independence is often just the beginning—have you had a chance to map out what your time actually looks like once you step back from the helm? Let’s catch up and see if your current asset structure supports that vision.
— The identity transition after a successful business exit.
Ahead of our meeting, I want to focus on the 'locked-in' nature of your current net worth. Given the current labor market and the unexpected tariff refunds flowing into the business, it's a good time to look at the tax-efficiency of a potential sale structure. Let’s talk about how we secure your personal future while the business is at peak valuation.
— Securing personal wealth amid business volatility.
Just now
Adobe is a global leader in software solutions for content creation, digital marketing, and document management. The company is currently heavily focused on integrating generative AI into its core Creative Cloud and Experience Cloud platforms.
Benefits Highlights
Common Financial Concerns
via Yahoo Finance
A major leadership change often signals a pivot in corporate strategy, which can impact internal morale, compensation structures, and long-term stock performance.
via Barchart
Strategic acquisition to bolster AI capabilities; indicates where the company is focusing resources and potential for future integration-related organizational changes.
via Adobe Investor Relations
Demonstrates financial resilience, but investor pressure remains high regarding the conversion of AI features into consistent top-line growth.
Adobe remains a financial powerhouse with consistent revenue growth, though the stock has faced headwinds due to market concerns over the speed of AI monetization.
Reflects strong demand, but growth must continue to justify current market valuations.
Trends
Aggressive shift toward GenAI integration
Impact: Increased pressure to ship complex AI features; potential for high-intensity work cycles in AI-focused business units.
Advisor angle: Discuss the impact of variable equity performance based on these high-stakes product launches.
Competitive Position
Market leader, but facing increased scrutiny regarding competitive moats against smaller, AI-native startups.
High technical hiring bar
Source: Recent job postings for Forward Deployed Engineers highlight a need for 9+ years of experience and deep LLM expertise.
These employees are highly compensated and likely hold significant amounts of unvested equity, making them prime candidates for complex tax and diversification planning.
Challenges
Market skepticism regarding AI monetization
Potential for short-term stock price volatility and pressure on RSU-heavy compensation packages.
Opportunities
Leadership transition
Provides a clear window to reach out to clients to review their financial plans and long-term goals during this transition period.
With the news of the upcoming CEO transition and the recent acquisition of Topaz Labs, I’ve been helping several Adobe employees take a fresh look at their equity vesting schedules. It’s a busy time, but it’s worth mapping out how these organizational shifts might impact your long-term liquidity plans. Do you have time for a brief check-in to see if your current diversification strategy still aligns with your goals?
— Proactive planning during organizational change
It’s been a while since we reviewed your concentrated stock position. Given the recent market volatility around Adobe’s AI strategy and the broader leadership changes, I’d like to ensure we’re still comfortable with your current risk exposure. When are you free for a quick call to stress-test your plan?
— Re-evaluating concentration risk
I noticed the shift toward Forward Deployed Engineering and the high technical expectations Adobe is setting for its AI teams. If you’re seeing your own compensation structure evolve as you take on these new, high-intensity roles, it’s a good time to ensure your tax and equity strategy is keeping pace. Can we look at your current grant schedule together during our next meeting?
— Wealth management for high-earning technical talent
2h ago
Habits Inc. operates a digital marketplace designed to connect millennials and young families with vetted financial advisors. The company focuses on lead generation and GTM infrastructure for financial professionals rather than managing client assets directly.
Benefits Highlights
Common Financial Concerns
via Fintech Global
Validated the business model and provided the runway for current operations; marks the point where equity grants were likely issued to early employees.
A lean, venture-backed startup currently scaling its advisor-facing platform. Revenue is driven by a subscription/fee-based model for advisors joining their network.
Seed capital supporting core platform development and early GTM efforts.
Trends
Increased competition for retail lead generation
Impact: High pressure to drive platform growth and demonstrate clear ROI to the advisor base, potentially leading to long hours.
Advisor angle: Discuss the trade-off between current income and long-term equity value in a competitive market.
Competitive Position
Niche player aiming to bridge the gap between digitally-native millennials and human financial advice.
Advisory-centric culture
Source: Public-facing portal requires interviews and approval for advisors, suggesting a brand focus on quality and vetting.
Employees likely value professional rigor and 'vetted' outcomes, which should be reflected in any financial planning approach.
Challenges
Maintaining a steady stream of high-quality leads for the advisors on the platform.
Revenue volatility can impact company valuation and the perceived 'in-the-money' status of employee stock options.
Opportunities
Early position in a fast-growing advisor-tech category.
Equity granted at this stage carries the largest potential upside on the cap table — planning done now compounds through every future valuation event.
I noticed your work at Habits Inc. as you've been scaling the platform to connect millennials with advisors. Managing the equity that comes with an early-stage fintech role can be a moving target, especially with the current shift in how firms are valuing lead-gen infrastructure. I’d love to share how we help startup employees balance their equity concentration with their long-term personal financial goals.
— Equity/Wealth Management
It's been a busy time for the fintech space, and I know the grind of building a platform that actually changes consumer behavior. If you’ve experienced any shifts in your role or compensation structure since your last funding round, it might be worth a quick look at your planning baseline. Are you feeling confident that your current equity strategy is aligned with your exit goals?
— Re-engagement
Since Habits Inc. has been growing its advisor database, have you had a chance to revisit your own tax strategy for your equity awards? Most people wait for tax season, but with the specific structure of startup options, there are usually better moves you can make mid-year. I work with folks in the tech space to keep their financial strategy as active as their day-to-day operations.
— Proactive Tax Planning
1d ago
Salesforce is a global leader in customer relationship management (CRM) software and enterprise cloud computing. The company is currently heavily focused on pivoting its product suite toward agentic AI and autonomous workflow automation.
Benefits Highlights
Common Financial Concerns
via Salesforce Press Release
Signals an aggressive move to integrate autonomous AI agents into the core platform, impacting engineering and product roadmaps.
via Axios
Positions the company and its leadership as primary drivers of global AI regulatory and ethical standards.
Salesforce maintains a strong market position with significant R&D investment directed toward its AI-first transformation. The company remains highly profitable, though it faces increasing competition for specialized engineering and sales talent.
Reinforces the 'Agentforce' strategy and AI roadmap.
Trends
Rise of Agentic AI
Impact: Shifts job roles toward AI-assisted workflows, increasing technical demands on existing product teams.
Advisor angle: Discuss the impact of this 'SaaSpocalypse' shift on the value of their equity vs. newer, unvested options.
Competitive Position
Holding strong, though aggressive poaching of GTM and sales staff by smaller, 'hot' AI labs creates talent attrition pressure.
High talent volatility
Source: Reported loss of ~100 employees to OpenAI/Anthropic in the first half of 2026.
Employees may be feeling anxious about the 'churn' or conversely, may be considering their own exits.
Challenges
Talent poaching by AI-native competitors.
Employees are likely comparing their current Salesforce RSU packages to potential equity grants at high-growth AI startups.
Opportunities
Integration of new AI capabilities.
High potential for performance-based RSU refreshes for top-performing engineers working on Agentforce.
I noticed the recent news regarding the acquisition of Fin and the continued rollout of Agentforce. These kinds of shifts often prompt a re-evaluation of your total equity compensation and long-term financial plan. Would you be open to a quick chat to compare how your current grant structure aligns with your personal financial goals during this company transition?
— Proactive RSU and equity review following company-wide strategic shifts.
Given the recent, broader industry trend of talent moving toward specialized AI labs, I wanted to reach out and see if you’ve had a chance to update your financial plan recently. Even if you're staying put, navigating the 'Agentforce' transition and its impact on your long-term equity strategy is a priority for many at your level. Are you feeling confident about your current portfolio diversification?
— Maintaining engagement with long-term clients by acknowledging industry talent shifts.
With so many moves happening in the AI space and Salesforce doubling down on Agentforce, I’m helping a few colleagues navigate the potential tax implications of their upcoming RSU vests. Since the landscape is moving quickly, I’d like to walk you through a few strategies to manage concentration risk while your role evolves. Do you have time for a brief check-in next week?
— Managing RSU concentration and tax risk during a period of organizational change.
Growth Begins With Habits | CEO @ usehabits.com
United States ·
www.usehabits.com
14,068 followers
A passionate communicator and advocate for financial literacy, Jack reaches millions each month across TikTok, Instagram, and LinkedIn, helping a new generation navigate money, wealth, life, and their careers with more confidence.
Jack is the CEO of Habits Inc., a venture-backed startup revolutionizing GTM solutions and infrastructure for the financial services industry. The company uses behavioral science, algorithmic matching and data to help financial service providers (authentically) reach new audiences, acquire more clients, and re-engage stale prospects.
Also, the startup operates a free-to-use financial advisor marketplace. Making your financial advisor search both simpler, and personalized to your goals, stage of life, budget, and experience.
The startup is backed by Atlanta Ventures, Elevate Ventures, Flywheel Fund, and notable angels including the former Vice Chairman of J.P. Morgan and founders of Holistiplan, as well as operators from AMEX Ventures, Techstars, and more.
Habits has since gained national recognition:
🏆 2025: People’s Choice Award Winner at 1871’s Fintech Summit (out of 46 startups)
🏆 2025: Voted Best in Show at Morningstar’s Investor Conference FinTech Showcase
To learn more, visit www.usehabits.com.
Jack Boudreau · 1st
Growth Begins With Habits | CEO @ usehabits.com
I left a $250k/year Wall Street career to start a fintech, and discovered a hard truth:
I was "too poor" for a decent financial advisor.
On paper, I thought I was the perfect client (~27yrs old):
- $150k in liquid cash/securities
- $300k in retirement assets
- $20k in crypto
- Zero debt
I was ready to pay. I wanted a strategy for the transition from "high earner" to "founder with zero income."
The result of five meetings?
- Three never called back.
- Two pitched me expensive insurance products I didn’t need.
- One told me to come back when I had a W-2 again.
I realized then that the traditional broker dealer model wasn’t built for people building wealth. It was built as a luxury service for people who are already done building it.
If you don't have $1M+ to stick in a managed account, or if your life doesn't fit the "9-to-5 until 65,” the legacy system views you as a risk or a waste of time.
Real financial planning (fee-only, fiduciary advice) has historically been a velvet rope institution. It was reserved for the ultra-wealthy, while everyone else got sent to call centers or sold commission-based products by a broker-dealer.
But the world has changed.
There is a massive generation of high earners, tech workers, and founders with complex lives who are being ignored.
That’s why I built Habits Inc.
14,068 followers
Jack Boudreau · 1st
Growth Begins With Habits | CEO @ usehabits.com
20h ·
Do you remember DARE?
If you grew up in the 90s you do. They marched us into the gymnasium, sat us cross legged on the floor, and a police officer explained why we should never do drugs. We signed a pledge. We got a t-shirt. Somewhere in a landfill right now there are millions of faded black t-shirts with red letters promising that an entire generation would Just Say No.
The whole premise was that someday we’d be standing in a circle, someone would hand us something, and the defining test of our character would be whether we could walk away. We role-played it. We practiced the exact words. It was treated as the single greatest threat our generation would face.
I’ve been thinking about that gymnasium a lot lately. Because they were right that there would be a substance. They just got the wrong one.
(Also, we just crossed 5k subs!!!!!!!)
Jack Boudreau · 1st
Growth Begins With Habits | CEO @ usehabits.com
3d ·
I swear there is nobody more stressed out than people in their 30s and 40s comparing themselves to the version of them that they imagined at 16yrs old.
(myself included)
Co-Founder & Chief Executive Officer
Habits · Full-time
Apr 2023 – Present · 3 yrs 4 mos
Co-Founder and CEO @ HABITS INC. Investors include Northwestern Mutual, Atlanta Ventures, Elevate Ventures, Flywheel Fund, and angel investors ranging from FinTech founders to industry executives.
Content Creator (100k+), Advisor & Consultant
Self-Employed · Self-employed
Apr 2023 – Present · 3 yrs 4 mos
Collaborating with brands on Instagram and TikTok, advising startups in Fintech, SportsTech, Marketplaces, and DTC, and consulting with enterprise-grade companies on brand and strategy.
Mentor & Advisor
Hult Prize Foundation · Part-time
Aug 2025 – Present · 1 yr
London, England, United Kingdom
Advisor, Board Member
Track Tennis
Jun 2022 – Present · 4 yrs 2 mos
J.P. Morgan
5 yrs
Banker Associate
Jul 2020 – Jun 2022 · 2 yrs · Chicago, Illinois, United States
Someone else made my powerpoints
Analyst
Jul 2017 – Jun 2020 · 3 yrs
I made powerpoints
Butler University
KEDGE Business School
International Exchange Student (IES)
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