If you’re a small business owner, you’re likely wearing every hat from CEO to marketer to part-time bookkeeper. But what about financial planning? For most, that’s a confusing and intimidating task. That’s where an AI financial advisor like Portfolio Pilot comes in. It gives you the personalized insights of a Wall Street strategist without the confusing jargon, hidden fees, or sales pitches.
This post dives into our conversation with Alexander Harmsen, Co-Founder of Portfolio Pilot, and how his AI-driven platform is changing the game for small business owners ready to take control of their financial future.
About This Huddle’s Guest: Alexander Harmsen
Alexander Harmsen is a seasoned entrepreneur and the co-founder of Portfolio Pilot, a platform built on the belief that everyone—not just the wealthy—deserves access to smart, trustworthy financial advice.
Before launching Portfolio Pilot, Alexander built a globally recognized autonomous vehicle company, where he helped develop regulatory frameworks for AI across nine countries. After exiting that company in 2021, he encountered the murky world of traditional financial advice—and realized how broken it really was.
What he found:
- Many financial advisors operate like salespeople.
- Investors often overpay in hidden fees.
- Personalized advice is reserved for the ultra-wealthy.
So, he built a solution.
“I wanted to empower people with a trustworthy second opinion. If we can do that—even just once—we’ve succeeded.”
— Alexander Harmsen
What Exactly Is an AI Financial Advisor?
An AI Financial Advisor leverages artificial intelligence, machine learning, and predictive analytics to deliver truly personalized, data-driven financial guidance. It examines your full financial landscape risk tolerance, tax exposure, income, investment goals, and your existing asset mix then translates that into clear, actionable recommendations. Unlike traditional advisors who may steer you toward products they profit from, an AI advisor is entirely unbiased, focused solely on helping you grow and protect your wealth.
Alexander Harmsen’s Portfolio Pilot is a standout in this space. Designed for everyday investors and small business owners, it connects securely to over 13,000 financial institutions from brokerages and banks to 401(k)s, credit unions, crypto wallets, real estate, and even student loans. Whether you’re building your retirement plan, analyzing investment opportunities, or just trying to get better financial visibility, the platform breaks down complex decisions into everyday language you can actually use.
Ideal for small business owners looking to optimize their financial future without a financial degree or full-time advisor, Portfolio Pilot helps you track, simulate, and improve your portfolio’s performance. It even calculates potential tax impacts and hidden fees helping you make smarter decisions faster. Best of all, as an SEC-registered fiduciary, it delivers trustworthy advice that puts your best interests first no strings attached.
A Real Case of AI-Driven Clarity
Take the story of a bakery owner in Colorado one of our Simply Be Found members who experienced firsthand how an AI Financial Advisor can transform financial decision-making. Like many small business owners, her finances were spread out: a Fidelity 401(k), a mortgage, a modest crypto portfolio, and some individual stocks sitting in Robinhood. She had income coming in, but financial visibility? Not so much.
After signing up for Portfolio Pilot and connecting her accounts, the platform quickly identified that 85% of her investments were overconcentrated in tech stocks a risk she wasn’t even aware of. Based on her risk profile and retirement goals, the AI suggested reallocations into dividend-paying ETFs, offering more stability and aligning better with her desire for predictable cash flow.
It didn’t stop there. Portfolio Pilot also uncovered a way to reduce her annual tax burden by more than $1,400, simply by tweaking where and how she held certain assets.
For the first time, she felt empowered not confused, overwhelmed, or unsure. She went from being reactive to proactive, from unsure to strategic. That’s the power of an AI Financial Advisor: making smart, tailored financial guidance available to real people, not just Wall Street insiders.
Why AI Financial Advisors Matter to Small Business Owners
Most small business owners don’t have time to manage their finances like a Wall Street analyst. They often operate with inconsistent income, limited retirement planning, and multiple liabilities. That’s why using an AI financial advisor is especially valuable for entrepreneurs.
Alexander built Portfolio Pilot with exactly this audience in mind. The tool is not only capable of analyzing complex financial data it’s also designed to simplify the experience. It provides a Portfolio Score, much like a credit score for your financial life, that gives you a clear understanding of where you stand, where you can improve, and what actions to take next.
Even more important: you don’t have to give up control. You don’t transfer your money into the platform. Instead, you connect your accounts securely and receive recommendations that you can act on or not based on your comfort level. That level of transparency and freedom is what makes this AI-driven model so trustworthy.
Alexander Harmsen’s Vision for Ethical AI Finance
During the Simply Be Found Huddle, Alexander Harmsen shared a powerful mission behind Portfolio Pilot: restoring trust in financial guidance through transparent, ethical, AI-powered tools. In a financial world where traditional advisors can profit whether you win or lose, Harmsen saw a fundamental misalignment and set out to fix it.
Unlike many advisory firms that charge commissions or a percentage of your assets under management, Portfolio Pilot uses a flat-rate subscription model more like a gym membership than a Wall Street firm. You pay a monthly fee, use the platform as much or as little as you want, and get access to cutting-edge financial tools and insights previously reserved for high-net-worth individuals.
One of the most striking revelations? Over 20% of Portfolio Pilot users already have a human financial advisor, yet still use the platform to double-check their strategies. Harmsen believes that just like we seek second opinions from doctors, we should be encouraged not discouraged to do the same with our financial decisions.
This approach is particularly powerful for small business owners and everyday investors who want financial visibility without hidden agendas. With Portfolio Pilot, the goal isn’t just automation it’s empowerment, transparency, and unbiased advice that puts you, the user, in control.
Simply Be Found’s Take on Financial Visibility
At Simply Be Found, we help small businesses show up across 1,000+ networks, search platforms, voice assistants, and maps. But what good is getting found if you’re not financially prepared to handle growth?
This is why we’re enthusiastic about tools like Portfolio Pilot. Just as our Listings Engine helps business owners get discovered by new customers, an AI financial advisor like Portfolio Pilot ensures that you’re making smart financial decisions as your revenue grows.
We believe visibility and financial confidence go hand-in-hand. You need both to succeed.
We often talk about how visibility is the key to growth. But visibility without financial direction is like driving without a map. As a small business owner, you deserve tools that not only get you noticed but also help you build wealth and stability in the long run.
An AI financial advisor like Portfolio Pilot isn’t just another app it’s a game-changing resource designed to empower you with clarity, control, and confidence. It’s the future of financial advice, built for real people with real goals.
So take the next step. Your future self will thank you
How to Start Using Portfolio Pilot
It’s easy to get started with Portfolio Pilot. Visit portfoliopilot.com and use the code podcast for a free month of Portfolio Pilot Gold. After signing up, the system will walk you through a four-minute onboarding process, asking you about your income, goals, risk tolerance, and preferences.
You can then connect your financial accounts—or simply upload a PDF statement. The platform will analyze your portfolio and provide a clear, actionable assessment within minutes. From there, you can explore suggested optimizations, build a draft portfolio, or track your progress over time.
Whether you’re just getting started or already working with an advisor, Portfolio Pilot gives you the second opinion and strategic oversight that most entrepreneurs wish they had.
Take Action Now
You work hard to run your business don’t let it stay invisible online. At Simply Be Found, we help small business owners like you get discovered on Google, voice search, maps, and over 70 major platforms. Whether you need better rankings, more calls, or more walk-ins, our tools and marketing coaches are here to help you grow.
✅ Start with our Listings Engine to get your business found across the web
✅ Optimize your Google Business Profile with our proven strategies
✅ Get expert support tailored to your goals—no tech skills needed
👉 Ready to take the next step? Visit simplybefound.com
📞 Or talk to our team today at simplybefound.com/contact
Let’s make your business easier to find and harder to ignore.
Transcript
- 0:00 | Intro: Meet Alexander Harmsen
- 0:10 | What is Portfolio Pilot?
- 0:29 | How Portfolio Pilot Integrates with Your Accounts
- 1:44 | Who Portfolio Pilot is Designed For
- 2:54 | How AI Delivers Financial Advice
- 4:05 | Onboarding Experience: Questions & Setup
- 5:45 | Linking Accounts & Privacy
- 6:33 | Personalized Portfolio Assessment
- 7:52 | Fiduciary Advice and SEC Compliance
- 9:08 | Control vs. Automation in Investing
- 10:16 | Support for Private Equity, Crypto & More
- 12:10 | How Taxes and Risk Shape AI Recommendations
- 13:44 | Portfolio Management Over Stock Picking
- 14:47 | Do They Profit from Your Trades?
- 15:53 | Building Trust Through Transparent Advice
- 17:04 | Second Opinions on Your Financial Advisor
- 18:41 | Real-World Scenarios Portfolio Pilot Solves
- 20:01 | A New Model of Financial Empowerment
- 21:47 | Using AI to Balance Risk and Goals
- 23:30 | The Vision for Portfolio Pilot
- 24:42 | Super Bowl Ad Dreams & Brand Expansion
- 26:26 | Comparison to Other Investment Tools
- 28:04 | Regulatory Edge from Founder’s Past Startup
- 29:38 | Why Alexander Entered Fintech
- 30:59 | Real Concerns About Traditional Advisors
- 32:05 | AI-Driven Portfolio Customization
- 34:02 | Helping Beginners Start from Scratch
- 36:01 | Top 3 Recommendations from the AI
- 38:07 | AI Unlocking Personalized Financial Advice
- 39:31 | How Portfolio Pilot Compares to Financial Advisors
- 41:12 | Launching Diversification.com for Investors
- 42:29 | Wrap-Up: Where to Find Portfolio Pilot
- 43:08 | Final Thanks to Alexander Harmsen
0:00 | Intro: Meet Alexander Harmsen
Alexander Harmsen, co-founder of Portfolio Pilot, joins the Simply Be Found Huddle. Robert introduces the conversation around AI, investing, and how small business owners can benefit from using smarter tools to make confident financial decisions. The episode sets the tone for a deep discussion on how technology is reshaping access to financial clarity.
0:10 | What is Portfolio Pilot?
Alexander explains Portfolio Pilot as an AI-powered financial advisor that offers real-time investment advice. It doesn’t just spit out stock picks it delivers contextual suggestions based on goals, risk tolerance, and financial health. This makes it a powerful tool for small business owners managing mixed portfolios who want to be smarter and more strategic with their money.
0:29 | How Portfolio Pilot Integrates with Your Accounts
The platform connects with over 13,000 financial institutions including brokerage accounts, crypto wallets, credit cards, and real estate assets. This connectivity enables Portfolio Pilot to analyze a user’s entire financial life and generate holistic, actionable advice all while keeping control in the user’s hands.
1:44 | Who Portfolio Pilot is Designed For
Alexander emphasizes that Portfolio Pilot isn’t just for traders or people who want to hand everything to an advisor. It’s made for the 78% of people who want to be involved in their financial decisions but need help navigating complex financial terrain. The platform empowers users to act smarter without needing to be financial experts.
2:54 | How AI Delivers Financial Advice
AI enables Portfolio Pilot to analyze goals, income, taxes, and risk to give smart, personalized recommendations. It takes on the heavy lifting crunching numbers across your accounts and predicting outcomes while leaving final decisions to you. The AI makes advice accessible, transparent, and efficient, even for new or busy investors.
4:05 | Onboarding Experience: Questions & Setup
Alexander outlines the onboarding experience, which begins with a simple but thorough questionnaire. Users answer questions about risk tolerance, income, marital status, goals, and more. It takes about four minutes and helps tailor the AI’s recommendations from the start ensuring that each user gets financial insights that are relevant to their specific situation.
5:45 | Linking Accounts & Privacy
Users can link brokerage accounts, crypto wallets, real estate holdings, and more or upload statements and screenshots. Portfolio Pilot supports over 13,000 institutions with bank-grade encryption and two-factor authentication. Privacy and control remain in the user’s hands while the system gathers financial data to offer a full picture.
6:33 | Personalized Portfolio Assessment
Once accounts are connected, users receive a complete portfolio assessment. The AI highlights where you’re strong, where you’re vulnerable, how you compare to peers, and where you’re overpaying in fees or taxes. It also shows how aligned you are with your goals, and provides insights for improving efficiency and reducing risk.
7:52 | Fiduciary Advice and SEC Compliance
Alexander discusses the challenges and importance of becoming an SEC-registered investment advisor. This legal status allows Portfolio Pilot to provide real, customized investment advice. It’s not just analytics it’s fiduciary-grade insight that takes responsibility for guiding users toward smarter financial decisions.
9:08 | Control vs. Automation in Investing
Users can choose between read-only views or enable one-click trade execution for supported accounts. Most people prefer control making Portfolio Pilot more of a co-pilot. You get suggestions, risk scores, and simulation tools. You decide if and when to take action, with the confidence that each recommendation is rooted in your full financial picture.
10:16 | Support for Private Equity, Crypto & More
Portfolio Pilot supports a wide variety of assets beyond traditional stocks like crypto holdings, real estate equity, angel investments, startup options, and private loans. The AI includes these in your net worth and retirement planning, treating them as real financial variables without forcing liquidity, helping users account for true financial health.
12:10 | How Taxes and Risk Shape AI Recommendations
Tax implications are a core part of Portfolio Pilot’s decision-making engine. The AI evaluates how asset decisions impact your tax exposure sometimes recommending you don’t sell because taxes outweigh benefits. Combined with portfolio correlations and personal risk, this makes the advice not only smarter, but genuinely personalized.
13:44 | Portfolio Management Over Stock Picking
Alexander emphasizes that finding the “next Tesla” isn’t the goal. For most users, making small, strategic adjustments across an entire portfolio has a far bigger impact. Portfolio Pilot helps users shift from a stock-picking mindset to a portfolio optimization mindset, managing downside risk, fees, and long-term gains more intelligently.
14:47 | Do They Profit from Your Trades?
Unlike traditional advisors who may earn commissions on trades or assets under management, Portfolio Pilot only charges a flat monthly fee. This removes all financial incentives to push specific products, creating a system that’s completely aligned with the user’s financial wellbeing whether you trade often or barely at all.
15:53 | Building Trust Through Transparent Advice
Alexander explains that the company designed Portfolio Pilot to remove bias and hidden incentives from financial advice. Users get clear portfolio scores and suggestions with no pressure to act. Even if you never trade, you still get tremendous value through guidance and understanding making trust a built-in feature, not an afterthought.
17:04 | Second Opinions on Your Financial Advisor
Alexander shares that about 20% of users already have a financial advisor but use Portfolio Pilot for a second opinion. It’s like getting another doctor’s diagnosis noninvasive, private, and insightful. Users upload statements or link accounts to see if their current strategy aligns with their goals or if there are missed opportunities or hidden fees.
18:41 | Real-World Scenarios Portfolio Pilot Solves
A bakery owner in Colorado used Portfolio Pilot to reveal that 85% of her assets were overexposed to tech stocks. The platform recommended diversified, dividend-paying ETFs more aligned with her goals and showed she could save over $1,400 a year in taxes. The result? More confidence, better control, and less reliance on guesswork or outside opinions.
20:01 | A New Model of Financial Empowerment
Portfolio Pilot empowers users without requiring them to move assets or commit capital. Alexander explains how users can explore AI-generated suggestions, simulate performance, and act only when ready. It’s about informed decision-making without pressure giving individuals control, clarity, and confidence over their financial future.
21:47 | Using AI to Balance Risk and Goals
The AI works continuously behind the scenes, weighing risk, liquidity, cash flow, asset correlation, and market trends. It adapts as users’ portfolios and life circumstances evolve, ensuring ongoing, personalized financial support. This approach helps users meet both long-term growth goals and short-term protection needs without stress.
23:30 | The Vision for Portfolio Pilot
Alexander shares his broader vision for Portfolio Pilot: democratizing high-quality financial advice that was once only accessible to high-net-worth individuals. With automation and AI, the platform offers elite-level insights to anyone business owners, families, or individuals who want more control and smarter investment strategies.
24:42 | Super Bowl Ad Dreams & Brand Expansion
Alexander humorously shares his dream of launching a Super Bowl ad that positions Portfolio Pilot as the “second opinion” for your finances. He envisions a memorable campaign like Larry David’s crypto ad that challenges the way people think about traditional financial advice while introducing a smarter, more empowering alternative.
26:26 | Comparison to Other Investment Tools
Most tools can tell you your asset breakdown but they stop short of giving actual advice. Because Portfolio Pilot is an SEC-registered advisor, it can legally tell you what you should do based on your unique profile. It doesn’t just report data, it interprets it, runs simulations, and recommends personalized next steps with real impact.
28:04 | Regulatory Edge from Founder’s Past Startup
Alexander’s experience building an autonomous vehicle company taught him how to work with regulators. That foundation helped him tackle the intense compliance needed to become a registered investment advisor. Weekly reviews, algorithm audits, and full transparency give Portfolio Pilot a legal and ethical edge in the fintech space.
29:38 | Why Alexander Entered Fintech
After selling his startup and speaking with financial advisors, Alexander realized many were just salespeople with biased incentives. Frustrated with the lack of transparency, he set out to build something better, an AI financial advisor that would act in the best interest of everyday users, not institutions or fund managers.
30:59 | Real Concerns About Traditional Advisors
Alexander and Robert discuss how many people unknowingly pay high fees or lose money through advisor mismanagement. Some advisors earn regardless of your portfolio’s performance. Portfolio Pilot aims to be a check-and-balance, an objective guide that helps users avoid being taken advantage of, while staying financially informed.
32:05 | AI-Driven Portfolio Customization
Alexander explains how users can explore as deeply as they want. The AI may surface a top-level recommendation, but users can dig into every assumption, run comparisons, and customize scenarios. It’s transparency by design giving people the ability to understand why each suggestion is made and to trust the logic behind it.
34:02 | Helping Beginners Start from Scratch
Even if you’re starting with no investments, Portfolio Pilot is ready. The onboarding questions alone allow the AI to deliver a personalized starting plan. Whether you have $10K in cash or are rebuilding from zero, the tool helps create a roadmap tailored to your timeline, risk tolerance, and long-term retirement or income goals.
36:01 | Top 3 Recommendations from the AI
To keep things actionable, the AI always surfaces a “Top 3” set of recommendations such as reallocating funds, optimizing tax exposure, or reducing volatility. Each suggestion is explained with clear outcomes and expected impact on performance, helping users stay focused and avoid decision fatigue while making smart, confident moves.
38:07 | AI Unlocking Personalized Financial Advice
AI makes it possible to offer elite-level advice to everyday investors. Alexander believes the biggest overlooked benefit of AI is its ability to deliver personalized insights based not just on market trends, but on each user’s exact circumstances, goals, and needs. It’s not just about faster data, it’s about better decisions.
39:31 | How Portfolio Pilot Compares to Financial Advisors
Many users split funds between Portfolio Pilot and a human advisor using it as a “performance benchmark.” The AI gives unbiased advice with no commissions, and many users realize they prefer its clarity and logic. It’s not just about replacing advisors it’s about helping people ask better questions and make informed decisions.
41:12 | Launching Diversification.com for Investors
Alexander introduces Diversification.com, a content and insights hub powered by Portfolio Pilot. It includes diversification scoring, macroeconomic news, and an alternative investment marketplace. It’s designed to cut through the noise of market hype and focus on data-driven insights for long-term, self-directed investors.
42:29 | Wrap-Up: Where to Find Portfolio Pilot
Listeners are encouraged to sign up at portfoliopilot.com and use the code podcast for one free month of the Gold plan. Alexander also highlights diversification.com as a powerful resource for staying informed with the latest financial trends and long-term portfolio strategies.
43:08 | Final Thanks to Alexander Harmsen
Robert closes the episode by thanking Alexander for his transparency, vision, and insights into AI-driven finance. They reflect on how platforms like Portfolio Pilot can empower small business owners and individuals alike to better manage their money with clarity, confidence, and control.
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About This Huddle’s Special Guest
