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Have you made a significant alternative source of income outside of your salary?

I am a senior product manager at a startup with a technical background and till date I have never made any source of income outside of my salary (or teaching assistant stipend in college). I know that I have the skills to improve my income significantly so I don't have to depend on my main job. But I am not sure what opportunities to pursue.
Hey, great question. Something that my husband and I are looking into is real estate. We hope to own a few properties over the next few years (and mind you, we don't make a lot of money at all in our current jobs) so this will be a very slow process. But I feel really excited about it and I think it has a lot of potential.
Yes -- I am an avid investor. I started out investing in mutual funds when I was a teenager and then became increasingly aggressive with my portfolio as I got older, which now includes emerging markets, commodities, VC, Angel investments, Art. I very specifically do NOT own real estate, not even a REIT.
Hey @BrianaBrownell, would love to hear more about how your investment strategy has evolved over time! Specifically, how have you gone about diversifying your portfolio (what do you weigh up when deciding whether or not to invest in something, what platforms are you using to invest, and how are you finding out about investment opportunities?), and how would you describe your attitude to risk?
Sure -- At the beginning when I was younger I invested in more stable, dividend yielding, large cap companies (which I still hold) because I was afraid of losing money. Right after university I got a job as a prop trader on the NYSE so I was much more immersed in the market. That experience was great because it taught me that I didn't have to be so worried about not losing money in the short term. I realized that I had lots of time ahead of me so I could be aggressive. From there I added precious metals, commodities and some emerging markets funds, which were very aggressive/high risk. Gold did well for me but the commodities (read: oil, etc.) definitely did not. I also invested in two VC funds which to be honest have not done well (but did give me a good tax break). I invested in a few art pieces as well, which are only partially "investments" and partially just pieces that I really love. (Much nicer than staring at a stock certificate) When I started getting more immersed in tech, I started investing in individual companies whose business models and technologies I believed in and I watch for IPO's. My top holdings are NVIDIA, Snowflake, Lemonade, and CRISPR Therapeutics. Just this year I started making angel investments and have four companies in my portfolio.As for how I find opportunities, nowadays it's honestly through my network. What trends and companies are people talking about? What industries are poised to be disrupted? What companies are other smart people investing in? I also attend the investor conference calls for different companies I'm interested in investing in. They are very enlightening as they allow you to see what industry trends and changes are happening. I also attend the Bank of Canada (I'm Canadian) quarterly calls (I don't know if there's an equivalent in other countries).
Really insightful! Thanks for sharing :)
I’m also looking to build a side hustle with some passive income. I’m working with my partner on a site that recommends skincare and we’re hoping to monetize without ads. We’re considering affiliate links for products on our site. I know that’s popular with newsletters I read. We’ve even considered micropayments based on usage or just asking for a small annual donation which I guess would essentially be a subscription fee. 😅 It’s interesting the different approaches because some are much more hands on than others! I’m not interested in leaving my job but want to diversify my income. Great discussion!
love this! I also am building a side hustle. Mine is a bit more hands on but would love to hear your journey.
I've been an entrepreneur for years but I've had a f/t job since July 2019. During the pandemic, I started a coaching business on the side. I coach startup founders and entrepreneurs. In my first month, I generated more income in coaching than in my job. I used that money for branding and a web site. I'm building an online business from my coaching business, I'm obsessed with making it happen and I'm looking for a co-founder. I've got the sales/public speaking/teaching/coaching/years of entrepreneurship experience and I want to find a hands-on operational co-founder who wants to scale this with me. For example, I just led a lunch & learn for a group called Funders & Founders. The topic was "I bootstrapped my company to $50 Million in 6 years, AMA." About 50 people attended and 11 people booked calls with me afterwards. I'm building up my list and my audience, and I have several clients on retainer and they participate in a Slack channel. I've owned companies with co-founders and have been a solo-founder. I prefer the former! If you're interested in doing this with me, I'd love to talk to you! My site is dianeprince.coside note, @MadisonMcCall Have you heard of Michelle Schroeder-Gardner's class on affiliate marketing? It's really good. https://makingsenseofaffiliatemarketing.com/?affcode=57702_hpj1mptd I'm curious what you mean by micropayments -- How would that work in your business?
Thanks so much for sharing @DianePrince! Curious what stage are the founders who come to you/find the most value in your coaching? Also do you find yourself doing some (strategic) consulting for them too or you limit to masterclasses?
Hi @iynna first of all I enjoy following your posts! Half of my clients are pre-revenue and half are around $250k- 1 million in revenue.  I do one on one individual coaching and there are lots of common things that come up that I’m going to turn into master classes, online courses etc. Common topics are establishing co-founder relationships, trouble with cofounders, navigating relationships with investors, how to pitch, cash flow, founder burn out, overwhelm, sales.
@DianePrince Thanks for the info on the class! Theoretically, users could be charged some tiny, fractional rate based on the amount of time their active on our site discovering products. I think it offers an interesting financial alignment between users and platforms but I don’t know of anyone successfully doing it. Interesting to think about!
I don't know what you define as significant (?) but I do have money in the market split into different funds/assets allocations for different goals, and the money has been growing nicely across the board.I do have a side hustle that can be done all online, and pays me a couple of hundred bucks every month - nice to be able to cover my bills with that so I can save and invest the rest.
Cool! What's your side hustle? I'm curious =)
My partner and I generate mid five figures in passive income via renting out the first property we bought together (lived in it for almost two years and aggressively paid down the mortgage on it--paid off in five years). This was only possible because we bought well below our means, to preserve optionality. I wouldn't necessarily recommend this path for everyone, because we were definitely the crazy cheapskates of everyone we knew, eg. mid-tier dinners out only for birthdays and anniversary, but also because we spend more time thinking about real estate than most: looking at open houses "just to check it out", browsing listings for various neighborhoods as a form of window shopping, running cashflow numbers on potential rental properties relative to investment costs. We also spend YEARS researching an area before moving quickly on a property we both like, so it's definitely not a fast ROI. My general advice is to choose a few different potential ideas that feel engaging and interesting and try them out temporarily (set an end date ahead of time to evaluate). That way, whatever you ultimately decide on for the second income won't feel like a grind in addition to your main job, but a fun project to work on in your off hours.