The Wealthy Parent Playbook: Using VC to Educate Our Kids
Real investing experience that builds lifelong skills - decision-making, patience, and strategic thinking

The next generation of wealth statistics show that the transfer of wealth from baby boomers to millennials and Gen Z will be in the trillions of dollars. As this transition unfolds in millions of households, many parents have begun to recognize the importance of preparing their children to manage their future inheritance responsibly.
Teaching children financial responsibility early on helps them set limits, budget wisely, and resist impulse spending. But when lessons feel abstract or dull, they often go ignored, failing to prepare kids for real-world financial decisions. To truly stick, financial education must be engaging, practical, and relevant to their lives.
Now, picture this: A 24-year-old at the Thanksgiving table, confidently dissecting a startup’s business model, debating market trends, and weighing risks with her parents. This isn’t a scene from a movie — it’s what happens when families use venture capital as a hands-on educational tool.
Instead of financial lessons fading into the background, young adults become active participants in real investment decisions. Whether through a structured program or alongside experienced investors, venture investing transforms abstract concepts into tangible experiences. Real deals spark meaningful conversations, fostering intergenerational communication, trust, and collaboration.
The result? Young investors develop sharp analytical skills, resilience, and a long-term mindset — learning more from real-world decisions than any parental lecture could ever teach.
How Venture Capital Teaches Wealth and Decision-Making
Venture capital (VC) investing can serve as a dynamic family classroom, blending finance, psychology, and strategy into real-world lessons. Instead of explaining abstract concepts like risk and reward, parents can demonstrate them through actual startup investments, making market research, competitive advantage, and valuation tangible and relevant.

More importantly, this experience fosters deeper family discussions about risk, reward, and value creation. Reviewing a potential deal together encourages questions like: What makes this business valuable? What risks do we face if we invest? How long might it take to see a return? These conversations go beyond financial literacy, helping young investors develop critical thinking skills. A teenager might ask, Why do we believe this founder can succeed? — leading to a broader discussion on leadership, resilience, and team dynamics.
Unlike stock trading or short-term speculation, venture investing naturally instills a long-term mindset. Startups take years to grow, teaching young investors that value creation requires patience and perseverance. For example, if a family invests in a biotech startup, kids can see firsthand how it might take 5–10 years for a company to go public or be acquired — a stark contrast to day trading.
Beyond financial acumen, venture investing exposes young people to groundbreaking ideas. It sparks curiosity about emerging industries, inspires creative thinking, and may even encourage future entrepreneurial pursuits. Even if they don’t launch their own businesses, they’ll develop an appreciation for innovation, resilience, and the transformative power of startups.
Ultimately, venture investing isn’t just about building wealth — it’s about shaping informed, forward-thinking individuals equipped to navigate an ever-evolving world.
Life Lessons from Venture Investing: Key Heuristics Beyond Finance
When families engage in venture investing as a learning tool, they encounter core venture capital principles — valuable life lessons in disguise. Here are some of the most impactful heuristics that can shape young minds.
1. Focus on the Wins: Resilience and Optimism
In venture capital, not every investment pays off — in fact, most don’t. Research from Harvard Business School shows that 75% of VC-backed companies never return capital to investors. Early-stage VCs expect 80% of their investments to fail, relying on a few major wins to generate overall returns.
For young investors, experiencing this dynamic firsthand teaches resilience. Imagine a family making five small startup investments, and over time, three of them fail. Instead of seeing it as a disaster, the family can discuss it as a learning opportunity: “In venture investing, losses are expected. What matters is that one or two winners might more than make up for them.”
The lesson? Don’t dwell on failure — focus on the wins. This mindset applies to life and career: doubling down on strengths is more productive than agonizing over setbacks. Through real investment decisions, young investors internalize that failure is a stepping stone, not an endpoint.
2. Time Frame Arbitrage: Patience + Long-Term Vision
Consider a family investing in a clean energy startup. After a few months, their teenage son asks, “Has the company made any money yet? When can we sell?” This sparks a conversation about long-term vision — the startup is still perfecting its technology and expanding its customer base.
Over the years, the teenager watches milestones unfold: new product launches, successful funding rounds, steady user growth. Eventually, if the company goes public or gets acquired, the reward feels even greater because of the patience required. This lesson applies beyond investing. Thinking in years, not days, can be a competitive advantage in education, career planning, and personal goals.
3. People Over Everything: The Importance of Team
Seasoned VCs say, “Bet on the jockey, not just the horse.” In other words, a startup’s success often hinges more on the team than the product itself. A 2020 survey of 885 venture capitalists from 681 firms found that 95% consider the team the most important investment factor.
Through venture investing, families can teach this crucial lesson. When the Saunders family considers investing in an ed-tech startup, they have their teens, Ava and Michael, research the founders. They learn the CEO built a successful education app, and the CTO is a former teacher turned coder. Around the table, the Saunders discuss how passion, expertise, and resilience drive success, reinforcing that a strong team matters more than just a good idea.
This lesson sticks. Michael applies it to school projects, choosing reliable teammates, while Ava sees how great coaches and players adapt to win. They both realize that whether in business, sports, or life, success depends on the people executing the vision.
4. The Prepared Mind: Curiosity and Continuous Learning
Louis Pasteur said, “Chance favors only the prepared mind” — a principle venture capitalists live by. They stay ahead by researching industries, tracking trends, and studying business models so they can act when the right opportunity arises.
For young investors, this implies that curiosity and preparation lead to better decisions. Before tuning into a webinar on an e-commerce startup, the Saunders have their teens research the market. Ava studies online marketplaces, and Michael analyzes competitors. During the webinar, they listen for answers to their questions.
Later, the parents highlight how preparation made all the difference. Whether they invest or pass, the lesson is clear: doing your homework leads to smarter choices, and opportunities favor those who are ready.
5. The Power of a Strong Network: Collaboration and Community Building
Success in venture capital — and life — is rarely a solo act. It’s often said that “Your network is your net worth.” A Harvard Business Review survey found that 60% of VC deals come through networks or referrals, proving that relationships drive opportunities.
Families like the Saunders use venture investing to teach the power of networking. At a startup event at the local university, Michael and Ava strike up a conversation with an investor, who later introduces them to a founder working on an AI startup. Instead of a cold call, they gain direct access through a warm introduction, showing them firsthand how connections open doors.
Back home, their parents emphasize that collaboration and helping others often lead to new opportunities. Who you know — and how you support them — can be just as important as what you know.
6. Learning How to Say No
One of the hardest lessons for an investor — or anyone with many opportunities — is learning to say no. Venture capitalists review hundreds of startups each year but invest in only a select few, requiring discipline, focus, and strategic decision-making.
For young people, this is a crucial skill. Through venture investing, they see firsthand why not every exciting idea is worth pursuing. When Ava finds a startup she loves, she’s eager to pitch it to the rest of her family. The demo looks great, but deeper research reveals red flags: a saturated market and shaky financials. The family chooses to pass.
Though disappointed, Ava later sees the startup struggle and pivot, realizing saying no was the right decision. Over time, she learns to prioritize what truly matters, whatever the field. Instead of chasing every opportunity, she focuses on the ones with real potential.
Beyond the Deal: Family Bonds and Lifelong Skills
Engaging children in venture investing goes beyond financial literacy. It strengthens family bonds and fosters critical thinking, confidence, and real-world decision-making. When families evaluate opportunities together, they shift from lectures to collaboration, turning parents into mentors rather than authority figures. Conversations about startups naturally evolve into discussions on values, risk, and success, helping children feel heard and respected while making financial discussions a natural part of family life. Many wealth advisors note that such open communication prepares heirs to manage wealth responsibly, rather than leaving them unprepared for financial independence.
Venture investing also builds confidence and independence in young participants. By analyzing risks, making decisions, and experiencing real-world outcomes in a controlled environment, children develop critical thinking and maturity. Engaging with real companies and stakes prepares them for future challenges, giving them a head start in navigating uncertainty — whether in college, careers, or major life decisions.
Another key benefit is fostering an innovative, entrepreneurial mindset. Exposure to startups working on breakthroughs teaches kids to approach opportunities and problems with creativity, persistence, and temperance. Even if they don’t become entrepreneurs, they develop a deep appreciation for innovation and problem-solving, making them more proactive, strategic, and engaged in the world around them.
10 Tips for Making Venture Investing a Family Experience
- Home
Gamify the Process
Set “rules” for choosing deals and introduce a points-based system for research contributions. - Home
Set a Budget
Define a specific investment pool (e.g., $5,000 or $50,000) to teach financial discipline. - Home
Provide Resources
Supply pitches, articles, and industry reports to encourage independent learning. - Home
Host Family Investment Meetings
Discuss opportunities regularly to keep momentum and engagement high. - Home
Ask, Don't Tell
Encourage kids to analyze investments by posing critical thinking questions instead of giving answers. - Home
Set Goals and Timelines
Track investment progress and lessons learned over months or years. - Home
Involve Kids at the Right Level
Younger kids can vote on startups, while teens can research industries and attend pitch webinars. - Home
Celebrate Milestones
Acknowledge company successes or personal learning breakthroughs. - Home
Encourage Reflection
Discuss why some deals succeeded or failed to reinforce decision-making skills. - Home
Normalize Mistakes
Frame losses as learning opportunities, not failures.

Investing in the Next Generation
Incorporating venture capital into family education transforms abstract financial concepts into real-world experiences, replacing lectures with lifelong lessons. In a hands-on, engaging way that traditional financial education rarely provides — children learn:
- optimism and resilience by focusing on big wins
- patience and strategic vision by thinking long-term
- the value of people and teamwork in achieving success
- questioning, critical reasoning, and research skills
- the power of networks, and
- how to build discipline by learning to say no.
For high-net-worth families, venture investing isn’t just about wealth — it’s about wisdom. It encourages meaningful conversations about values, legacy, and impact, helping children understand the problems they want to solve and the change they want to create.
The ultimate return on investment isn’t just financial — it’s raising capable, thoughtful adults who understand risk, reward, and long-term thinking. In the end, venture capital isn’t just a financial tool — it’s a way to invest in your family’s future.
If you’d like a venture partner in this experience, please reach out. By co-investing alongside experienced VCs, families can ease into the process, growing their knowledge and comfort over time and tapping into a firm’s deal access. And we invite you to explore the venture videos, blogs, and interviews you’ll find on our website.
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This communication is from Alumni Ventures, a for-profit venture capital company that is not affiliated with or endorsed by any school. It is not personalized advice, and AV only provides advice to its client funds. This communication is neither an offer to sell, nor a solicitation of an offer to purchase, any security. Such offers are made only pursuant to the formal offering documents for the fund(s) concerned, and describe significant risks and other material information that should be carefully considered before investing. For additional information, please see here. Example portfolio companies are provided for illustrative purposes only and are not necessarily indicative of any AV fund or the outcomes experienced by any investor. Example portfolio companies shown are not available to future investors, except potentially in the case of follow-on investments. Venture capital investing involves substantial risk, including risk of loss of all capital invested. This communication includes forward-looking statements, generally consisting of any statement pertaining to any issue other than historical fact, including without limitation predictions, financial projections, the anticipated results of the execution of any plan or strategy, the expectation or belief of the speaker, or other events or circumstances to exist in the future. Forward-looking statements are not representations of actual fact, depend on certain assumptions that may not be realized, and are not guaranteed to occur. Any forward-looking statements included in this communication speak only as of the date of the communication. AV and its affiliates disclaim any obligation to update, amend, or alter such forward-looking statements, whether due to subsequent events, new information, or otherwise.
Frequently Asked Questions
FAQ
Speaker 1:
Wealthy Parents Playbook. We’re going to talk a little bit today about the benefits of venture investing as a family activity, and this extends far beyond the financial dimension. A lot of our investors have found some real benefits, and Alumni Ventures—especially with our syndication program, where we share information and data room and deal analysis—is a great vector for this to be a very practical solution. So I’m looking forward to today’s webinar.
Before we get going, we’re speaking today about Alumni Ventures and our views of the associated landscape. This is for educational purposes only. It’s not an offer to buy or sell any securities, which are made pursuant to formal legal documents. And off we go.
This is what we’re going to cover today. First of all, there’s significant wealth transfer that has been created by the boomers that’s going to be transferred to the next generation over the next 20 years. VC is a fantastic classroom. Just some lessons both from venture investing that applies to life and then beyond investing itself, and then some tips and tricks for how you can actually go about doing this in a big way or an incremental way.
Just a couple minutes on me and Alumni Ventures. I’ve been in the business since 1986, started Alumni Ventures to bring a smart, simple venture portfolio and deal access to retail investors. We’re listed as one of the most active venture capital firms in the world and have built really a pretty good reputation among the retail investor class and our portfolio companies. We’ve raised just about $1.5 billion. We make investing very accessible to accredited investors with low minimums, and we have a hundred employees plus—about half in the back office and half in the venture hubs. We’re co-investor only, so we work with among the top venture capital firms on the planet. We’re, I think, thought of very well as a really strong co-investor. I encourage people to check out our portfolio companies. At the end of the day, this is the measure of a venture firm—the companies you invest in and how they do. So our Apex 50 is a condensed version of it, so pretty easy to access and read that report. We’ll be sending this deck along as a resource, encouraging you to share it with family and friends. Hopefully, you’ll strongly consider investing more as a family.
Again, most of you are familiar with these names. These are the kinds of firms we co-invest with. Over half of our investments are with the top 100 venture capital firms as the lead. And there’s also up-and-coming, vertically oriented firms that we like to invest in certain niches as well.
So let’s hop right into it. First point is most people are familiar with the incredible wealth creation that the boomers have developed. That value will be moving on to the next generation—Gen X and millennials. That is just starting to happen and will take place really over the next 20 years as the boomers pass on their wealth to the next generation. I think a lot of parents want to be sure that the next generation is good stewards of that resource and does good with it, and I think it’s a really tricky but important job to find vectors to educate the next generation. But a lot of money’s flowing that way, folks.
So just a few points, and we’re going to make this pretty direct.
When you look at a venture deal, it is about the tip of the spear of investing. So a lot of investments are analyzed in hindsight. This is a real-time, realistic fundamentals-of-investing brought to life. So all the things—from financial to team to market opportunity to business models—that’s capitalism, and looking at a venture deal brings that into really strong relief.
I think one of the key takeaways is this is something that a lot of people find very interesting and want to get involved with. So it’s one thing for those of us that are parents—and again, I’ll just speak personally, I have three adult kids—getting your kids to engage in things that they’re not interested in is like pushing on a string. But when you talk about investing and technology and valuing their opinion and analysis and vote, it is a great opportunity to engage and have meaningful conversations about money, about risk, about values.
We live in a world that requires critical thinking. It is very short-term oriented. Venture capital thinking really, again, exercises the muscles of analysis, debate, patience. We’re also talking about where the world is heading. Technology innovation is upstream to the world and things that will impact careers and family decisions and politics and life. And understanding what’s happening, what’s a fad, what’s going to change the world—that curiosity, that entrepreneurial thinking—is really important to developing a mind for the next 30, 50 years.
I also think about the venture mindset—and I write about this extensively—build skills that extend way beyond just investing when it comes to relationships, career development, any kind of decision making. I think there are really important venture capital lessons that can apply, and I’ll talk a little bit about some of those today.
But VC is an excellent classroom. So I’m going to just talk about six of the very important things that I think matter that can be communicated through looking at a venture deal as a family.
Number one: Venture capital is a power law business. It’s about your wins, not your losses. That is an important life lesson. We live in a society that frankly doesn’t encourage a lot of risk and failure among young people. The ability to learn grit and resilience—again, venture capitalists are judged by their wins, not by their losses. It is a power law business, and I think that applies to life. Your good decisions are so much more important than the setbacks. So I think this is a great training tool to understand asymmetric risk. I think it’s a great area to be talking about compounding—the power law wins paying for losses. And again, I think there are lessons in education and throughout life that this is a really important life lesson.
Time arbitrage. We live in a world that is frankly about getting rich quick. It is about quarterly earnings. It is about now, now. Attention spans are encouraged to get shorter. However, if one can think about things for longer time horizons—what I call time arbitrage—whether that be in your career, personal goals, education, developing a family—thinking about medium and long term is a really important muscle to exercise and develop.
Venture capital really forces us to talk about investments that take years before you even know if it was a good or bad investment. So just watching that development from a company over time, I think, is a really important lesson about the value of time, patience, compounding, grit, perseverance. The great companies—whether it be Apple or Amazon—lived through kind of near-death experiences. Most of us in our careers have had ups and downs and setbacks. And again, I think all of us want to communicate to the next generations the importance of grit, patience, compounding—getting really good at something that takes a long, long time and is hard.
The importance of people. Venture capitalists really bet on teams. So when you look at a deal as a family, you spend a lot of time on: What do you like about this person? What do you think about their background? What signals are you getting that they’re going to have the grit, have the know-how, and are uniquely positioned to be successful in this?
Again, really broad applications to life. People. Decision making is one of the most important skills that a young person can make and develop. So I think this is a great opportunity to, in a non-direct way, teach those lessons. And so that’s a little bit of the art of this—instilling these without a lecture, but through examples, discussions, debates. People over everything.
Lesson four from venture capital is about curiosity and learning and having a prepared mind. Great venture capitalists connect dots, read, study, learn, are curious. Again, a great lesson for life. The connections that people make professionally, where you can assign assignments and learn things that apply to something else down the road, is just invaluable.
And so anything that we can do to encourage curiosity and learning and open-mindedness and jumping on new things, trying new things, and having a prepared mind is incredibly valuable to pass on to our kids.
The importance of networks. Greatness is achieved in the agency of others. Alumni Ventures is a network-powered VC firm. We’ve built our very successful business with a simple idea—that we can do better together than any of us can do on our own in this asset class. And getting people—especially post-COVID—out of their apartments and into the world, meeting people, networking, learning, having parties, attending networking events, going to real-life places—those things pay off. The importance of developing your friend network, your social network, your professional network, your hobby network.
And this is, again, brought to life through venture capital work. Most of our deals are sourced from our community. Our due diligence—people you can ask, people you can check with. People are always interested in sharing their points of view and opinion. Learning to take that input and put it through your own filter. Using tools to help you network. All of these are super important lessons that can be brought to life through venture capital.
Learning to say no, right? This is a skill that, again, is right at the center of venture capital, where you look at a hundred deals to do one. So the ability to be biased toward what can go wrong—but also what can go right. Learning that not every exciting deal on the surface is worth doing. This, again, applies to relationships. This applies to career development. This applies to other types of investing.
So again, I like, as our family does, having a budget—determining how many deals we want to do together per year as a family. Is this one of the punch cards we’re going to click to do this? So these kinds of selective decision making things, again, are an important part of development—of judgment, decision making, budgeting. A really great lesson about learning to say no.
And that’s just a few of the things. I would also say that as one kid grows, opportunities to have discussions, meetings, developing mentorship, and sponsorship in a way that people all feel that they’re listened to—participate with—here.
These are lifelong skills. I learn from my kids every day. It also builds a lot of confidence, a lot of independence, a lot of critical thinking and maturity. And we live in, frankly, an entrepreneurial, innovation, tech-driven world. And so exposure to this subject area I just think is a really important Venn diagram between what you want as a parent, what the kids are interested in, and what is good for society. So really important extra benefits.
So here are some things we wrote down as a team where we’ve seen other families do this successfully. They gamify it. We live in a world where it’s like—there are rules for how we’re going to do it. Who votes? How many deals are we going to look at? What’s our budget? How are we going to decide?
These things are really covered here in number one. And number two, obviously sharing information, reports. I think a combination of independent work and some family discussion is the optimal way to do it. It doesn’t have to be complicated and long. But—hey, the team, the family’s looking at a deal. We’re going to vote. Here are the materials. I want to hop on a Zoom call Saturday afternoon. Who can make it? And if not, send in your proxy.
As a leader, I think that it’s really important—whoever’s leading the charge here—to ask a lot of questions, encourage participation, empower people, require responsibility, and take ownership of things. I think documentation is good. Again, I’m kind of a nerd, but we have kind of a family record keeper.
Obviously, you want to develop this at the appropriate level for where your kids are at. The difference between a 13-year-old and a 23-year-old and a 33-year-old is pretty significant. But I think the earlier, the better. You start talking about this, I think there’s—when things work out—I think those things are always important to celebrate and discuss. And when things don’t work out, you have a discussion about whether we learn anything, but without assigning blame or mistakes or those kinds of things. Again, this is venture capital. We do this as venture capital partners.
It is, as I mentioned, about your wins, not your losses. But again, always trying to learn and get better and do things. So again, I think this is a really fun, interesting tool to do something that frankly isn’t taught enough—about being an investor.
Again, even if you have multiple kids, you’ll often find one, maybe two kids are interested and others are not. But you want to bring ’em all along and have ’em all participate from their own perspective. I think a family that invests together stays together. So really important.
Again, I’ll just emphasize this again one more time—this is more than just about money. It’s about values, wisdom, and critical thinking. I think it’s very important when we’re talking about the tens of trillions of dollars that’s going to be passed on to this generation. It’s an important part of legacy to be sure that we’re developing future leaders and that we’re raising thoughtful, analytical, capable adults.
And this can be something that can happen over time. It is not a light switch. So we’re all learning every day. I’ve been at this business a long time and I still learn lessons every day. But it’s a really fun and interesting way, and there’s so much great material now. And what we’ve seen with other families is they start out a little bit, and it can really light a fire under some people to learn, listen to podcasts, read articles—and sometimes even change the trajectory of their own interests and career.
So this is just a little bit of a wrap-up now about Alumni Ventures and how you could potentially work with us on bringing your family into this.
Again, just really briefly, we work with a variety of different personas—from the newbies to people who are really interested in alpha. We have people that are in the pay-it-forward camp, all the way through to the channeling of Warren Buffett and are looking at this as just a pure analytical asset allocation play. So we want to listen, we want to help, we want to help you craft your program for your family.
I’ll bring, in particular, the AV syndicate—where you look at an individual deal. We share our deal room and it’s kind of opt-in. So even if you’re never going to invest in a syndicate, I would use it as an opportunity for education with your family.
So again, Alumni Ventures—we’d love to be your venture partner. Again, a lot of people want to kind of hit the ATM machine and learn on their own. Private QR code to view some of our materials. Other people just prefer to talk or attend a webinar. We encourage you to schedule a call. We’re good listeners. We’re not pushy salespeople at all. And if you’re an existing investor and just want to kind of get a refresher on some of our funds, your individual portfolio, and how it’s doing—putting together your plan—again, we have people that are really good at it and encourage you to reach out to a contact person at us.
So with that, I think we have time for a few questions from the audience today.
Yeah, the first question is really regarding: how early do you get started with kids?
I think middle school is where we started with our kids—starting to talk about money and investing and assigning responsibility—and then just keep building on that over time. Right now, we have basically a family meeting every quarter. We look at deals as a family probably on a monthly basis. Everybody has an equal vote. Right now, we’re actually five people as a family. So it’s simple majority rule.
We have a budget. We have good, healthy discussions. People find their niche. I think it’s fun, it’s interesting, but I think you want to just kind of—and your kids are all different—so you’re going to want to meet them where they are. But nudging in this direction, I think, is something you just don’t want to ignore. But looking at specific deals is a great way to start that dialogue.
How do you deal with your mistakes and losses without discouraging them?
So one thing about it is just being open and explaining from the get-go: what do we think the chances of success of this thing are from the get-go? So you do kind of a pre-mortem. You’re monitoring as it goes along. And for the winners, you’re humble. And for the losers, you’re teaching the lesson that you’re probably not as smart as you think you are in the good days—and not as dumb as you feel when things don’t go well.
So again, a great opportunity to teach about grit and perseverance and moving on from failure.
How can AI help? That’s a great question.
What a fantastic tool to explain terminology, or to bring up good questions or good points. It is remarkable now, and it is a really important reality that this next generation is going to have—which is the ability to have an expert in something as kind of your silent partner. Reviewing deals, reviewing documents, preparing questions, preparing agendas, doing risk assessment, teaching you terminology that you might not be familiar with.
The beauty of AI is you can say, “Hey, explain this to me at a middle school level,” or, “Explain this at a high school or college level.” “What are some approaches that we should think about when we look at this?” So yes, I think it is a key point. I wish I’d have made it, frankly. Thank you for the question, which—absolutely—AI needs to be your partner in this process. So great question.
So again, thanks everybody for joining today. I think this is something I hope you guys think about. Consider hopping on the phone with us. AV syndications are kind of a great way to bring this to life. We make them available every week or two. And so thanks for your time today. I appreciate it.