From the Diary of Anna Magiera

The questions Anna Magiera asks before she discusses any deal, and why she thinks private investors should answer them first.

When someone asks Anna Magiera, “Where should I invest?”, she usually answers with more questions. What are you trying to achieve? What is your time horizon? How much liquidity do you need? What level of risk are you comfortable with? How much of your overall capital are you prepared to allocate to high-risk, illiquid investments? “Only then,” she says, “does it make sense to talk about asset classes and individual opportunities.”

She says that because it is their own private capital, investment decisions “can become very personal.” Aspiring investors listen to friends or acquaintances, “look at what others are doing, and try to replicate it,” without necessarily knowing the full context behind those decisions.

On picking winners, she is direct. “No one knows in advance which one or two companies will become the winners,” she says. “If we did, there would be no need to build a portfolio.” The numbers behind that are not new. A 2007 Kauffman Foundation study of 539 angel investors in North American angel groups found that 52 percent of their exits returned less than the capital invested, while the 7 percent of exits that returned more than ten times the money accounted for 75 percent of the total dollars returned.

Anna is the ICLUB Managing Director, Partnerships & Education, and she leads ICLUB’s education initiatives, including ICLUB Angel Academy, a practical program that helps aspiring and existing angel investors build the knowledge, tools and strategy to evaluate startups and develop their portfolios. She describes ICLUB as a global angel investment community of more than 8,600 investors, backed by TA Ventures, that connects private investors with high-growth tech startups worldwide.

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Ten or More Startups

The same principle applies, she says, when the asset is a private company. “The question isn’t simply ‘Is this a good company?’ It’s also ‘Does this investment make sense within my portfolio and strategy?’” For angel investors, she has written, she would aim for 10+ startups, and with a budget of $50k+ that is possible through syndicates and investment clubs such as ICLUB. Her checklist of what not to do begins with investing $25-50k in a single startup if that represents a significant part of a venture investment budget. It also asks for deep due diligence on every deal, conversations with people “who can challenge your investment thesis rather than confirm it,” a circle of like-minded investors to discuss deals with, and regular updates agreed upfront.

Recently, she says, one of the investors she works with published an article about his portfolio across different asset classes. He highlighted two private companies as his bets to generate significant returns, which she calls “exactly the mindset we try to challenge.”

“You can’t eliminate that risk. But you can avoid concentrating it around a few bets simply because someone else believes they will win.”

Anna Magiera, ICLUB Managing Director, Partnerships & Education

At ICLUB Angel Academy, she says, the goal “isn’t to find the one winning deal” but to build a portfolio that gives exposure to potential winners while managing the inherent risk of investing in private companies. The Kauffman study shows what holding more than one looks like: although 52 percent of exits were at a loss, 61 percent of the angel investors had portfolios that returned more than they put in.

The numbers and the founders are two things she learned in two different places.

Both Sides of the Table

As she puts it on her profile, Anna has about 20 years across corporate advisory, venture capital and startups. Her background includes advisory work at EY and PwC, leadership roles in venture, PE and CVC funds, and running acceleration programs. Over the past decade, that has included working closely with 250+ startups as an investor, mentor and board member, across SaaS, AI, FinTech, PropTech and other tech sectors. She is also a board member of StartUp Hub Poland.

She says the two kinds of work taught her almost opposite things. Corporate advisory taught her structure: how businesses are analyzed, how decisions are supported by data and how risks are identified. Working with startups taught her how to make decisions when the data is incomplete and much of the value still lies in the future. Having worked on both sides, she says, she naturally looks for both.

“I want the numbers and the structure, but I also understand that an early-stage company cannot be evaluated like a mature business.”

Anna, ICLUB Managing Director, Partnerships & Education

For an early-stage company, she says, that means looking at the founders, market, timing and potential, while understanding which risks are inherent to investing in private companies and which are genuine red flags. She says that combination has shaped both how she invests and how she teaches investing.

There have been many hard moments over the years, she says, and she tries to see them as “challenges I can overcome rather than setbacks.” She adds that she is lucky to have a strong support system around her.

Asked which one person shaped her, she says she can’t name just one. “At every stage of my career, I’ve been lucky to have people who believed in me, vouched for me, taught me, mentored me, and gave me opportunities to grow.” When she started in venture, she wrote, she worked with some of the best in the industry, people genuinely open to sharing their knowledge, experience, mistakes and lessons learned, “true mentors, without ever using the term.” Now, she wrote, she finds herself on the other side.

How the Academy Grew

By her own account, the Academy was not planned. “And just like that, I somehow became an educational product owner,” she wrote. It began as a short YouTube series and turned into a deep-dive course and then an Alumni Club, all in six months, “without me planning it. Just doing it, one step at a time.”

The Alumni Club began after the first cohort, she says, when participants wanted to continue meeting, discussing deals and learning from each other. Today it brings together members from three Academy cohorts, 35 private investors in all, and “with every new cohort, the community keeps growing.” Members meet regularly, discuss current deals and startup financial models, run Investment Committees, invite guests and learn from each other. She calls it important evidence that the value is not only in transferring knowledge but in a community where private investors keep learning and becoming better investors long after the program ends.

She wrote that discussions regularly run well past the scheduled time, and that she is humbled by investors trusting her to guide them into “a world I’m slightly (okay, very) crazy about.” Most importantly, she wrote, seeing people become more confident in their investment decisions is among the most rewarding parts of it.

Where Anna Is Now

That is the work she wants more private investors to join. The readers she most wants to reach are private investors and family offices, particularly those interested in private-market opportunities beyond public markets who want to understand how to approach them, build a portfolio and make more informed investment decisions. Over the next years, she says, she would like this work to bring more of them into the Academy and the community around it. She wants to keep building both “into a place where a new generation of private investors learns to invest with more knowledge, confidence and strategy.”

Outside work, she runs, something she came back to recently. She likes it for the same reasons she likes building things professionally: “consistency matters more than one great day.”

Five Reflections from Anna

Does this investment fit your portfolio and strategy? Beyond whether a company is good, she asks whether the investment makes sense within the portfolio and the strategy.

Whose bets are you following? She says investors listen to friends and acquaintances and try to replicate what others are doing, without necessarily knowing the full context.

How many bets are you making? She has written that as an angel investor she would aim for 10+ startups.

Who can challenge your thesis? She has written that you should talk to people who can challenge your investment thesis rather than confirm it.

What happens after you wire the money? She has written that investing does not end there, and that regular updates should be agreed upfront.