Hi I'm Andy, ask me anything about bootstrapping, angel investing and portfolio careers.

Andy Ayim
35 replies
Hi Makers 👋, I'm Andy, author of Breaking into New Careers and EIR working on an Angel Investing School for patient capital, AMA 💰 I've had a portfolio career, starting off as a management consultant, before cofounding a bootstrapped startup (that my brother still runs today), starting a business within a business twice, developing my craft as a product manager, to joining the Obama Foundation Emerging Leaders programme and being named in the FT as a Top 10 BAME Leader in Tech. 🤔Recently published a new ebook called Breaking into New Careers for career transitioners who want to develop a personal brand, attract new clients as they freelance and balance working on their side projects. I believe the first page of Google is your new CV and this book explores how you can own it! Here to answer any questions about bootstrapping, angel investing, diversity in tech, portfolio careers, journaling, writing, transitioning into new careers, startups, personal branding, mental models, guiding principles, product management and me! 😊


I'd love to hear more about how you got started in angel investing. Do you have any tips you can share for folks like me who are interested in getting into this in future? Thanks
Andy Ayim
@abadesi Honestly my first step was in building a balanced portfolio in other asset classes such as property and index funds. Then I saved up 5% of my yearly income for 2 years and started investing as little as £5K into startups I was forming relationships with at events, through friends and finally as a scout for a small angel syndicate in the UK.
@andy_ayim this is really helpful, thanks for sharing the personal finance mgmt tips in your response.
James Okon
@abadesi @andy_ayim can we chat over these aspect of your achievement...what are your parameters and standards for commitment to invest and shortlist for future consideration....and your follow through schematics!...thanks
Andy Ayim
@abadesi @james_okon1 In terms of parameters for investment, I think quite different to most early stage investors I speak to. I invest in startups with patient capital, similar to value investors in PE whereby I am investing in a long term relationship with founders aligned with long term value creation beyond the capital. Parameters are as follows: 1. Investment terms where investors receive dividends through revenue-share, built to preserve optionality for founders and support long-term ownership and control. 2. Revenue sharing funds aimed at helping startups go from £100K to over £1m+ revenue 3. Invest in startups with product/market fit and high returns on operating capital. This rules out any businesses that do not sell direct to consumer or do not make goods consumed at short and regular intervals. This is my circle of competence which I know well and stay in (can be tech enabled not necessarily SaaS). Good businesses I would loved to invest in that fit this thesis include 1Password, The Shade Room, WorldStarHipHop, no code tools like Bubble and digital media businesses that have rich digital presence through digital service providers on content platforms like Spotify, Youtube and others. Hope that helps.
Quincy Lun
@andy_ayim What are some of the terms you made with startups for an investment of £5K?
Mitch Gillogly
Any advice on building a fintech company, specifically one in the lending space that's capital intensive?
Andy Ayim
@mitchgillogly Honestly compliance and regulation is one of the major barriers aside from liquidity. It would help to get advisors that know this space well. The challenge with lending fintechs is that investors are now leaning more to valuing them as a lending book rather than a fintech solution as Prosper, Lending Club and Funding Circle were leveraging people more than tech in administrating the loans.
Rhona Aylward
Hi Andy, I'd love to know if Angel investors value companies that have bootstrapped for a while (>1 year) before looking for investment, or do they prefer to get in early before there is any real revenue?
Andy Ayim
@rhona_aylward angel investors are not a homogenous group, in fact the challenge is that they are so fragmented. Angel investors such as Rob Walling, founder of TinySeed and former founder of Drip loves investing in bootstrapped SaaS founders. Others invest in the domain expertise they know well. All investors favour traction as it lowers the risk of failure (never fully eliminates it).
Kenji Sano
Hi Andy! Have you ever reached $10K MRR in less than 3 months? If so what was the Average revenue per customer. Thanks!!
Amarpreet Singh
Hi Andy, I would love to get some recommendations from you over entering angel investing, got some tips? would love to hear them.
Andy Ayim
@amarpreet25 Understand term sheets, cap tables and at least an industry or domain where you have access to a network and some expertise. Also look for active angel investors you can shadow or learn from even if that means joining a syndicate on angel list just to learn. Personally, skin in the game is the best lesson, but a small enough amount that you can afford to lose. Treat it like a heavily discounted angel investing MBA where you can invest as little as $1000 - $5000 and learn how to source, assess, invest and support founders, adding value beyond capital.
Abey Koshy Itty
Hey Andy! How do you go about with marketing when you're bootstrapped?
Andy Ayim
@abeykoshyitty The key thing is to: 1. understand where your customers hang out online (subreddit, hacker news, Fb Groups, Slack communities, Quora) and become a trusted contributor and give, give, give value before asking. 2. Do the same offline by attending events (search on Eventbrite, Meetup and company events within specific industries where you believe your customers will be). 3. Deliver a great product experience, from discovery and onboarding to first use, this is the most cost effective marketing method. One of word of mouth (like Whatsapp and Instagram did well).
David McQueen
What recommends do you give to people looking to start out in angel investing?
Andy Ayim
@david_mcqueen I would advise the following 3 things: 1. Do you understand the risk profile of the asset class? - Make more money than your bank account's interest? -> Due to the high probability of failure your bank is a far lower risk even if the returns are small. - Make more money than investing in index funds? -> median return of index funds outperform venture capitalists. - Find & invest in a unicorn? -> Less than 0.1% startups make it here. 2. Can you afford to lose what you invest? - highly likely you will lose it so best to look at other benefits you are more likely to gain such as founder empathy, the struggle of scaling a startup, term sheets & cap tables, sourcing & assessing deals, providing support and governance, is this something I want to continue or not etc...... 3. angel investors are largely operators with domain expertise who can add value beyond the capital. Can you? - what is your circle of competence? - where do you have deep networks & relationships? - are you willing to be there during the tough times when things are not going so well? - are you willing to be an extension of the startups team helping with anything from hiring to business dev?
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Walid Shaar
@andy_ayim That sounds amazing! Any advice would be taken into high consideration. We are a Start-Up Based in Lebanon. We have created Ring n Bring. A Smart Service Bell for internal ordering at homes and households. We have launched a campaign to UAE, and getting only a few sales. How do we know if its the Product or something else? What do you suggest to bump this up? Please check www.ringnbring.com to know more Any feedback would be greatly appreciated! P.S. Working on a new website design/messaging that will be released soon. Key changes: More emotional, Respecting white spaces, Giving Brief and Concise description of product...
Andy Ayim
@walid_shaar you need to conduct user interviews with the people you think are your users. Find out about the problems users have in their home when ordering. Learn about the existing alternatives. Learn about their frustrations. Do an observational study and ask them to carry tasks out and see what they do and why. You need to pause putting money into ads and first understand who your user is and whether your solution adequately solves their problem.
Tom Larder
Hello Andy, nice to digitally meet you! What information, and in what format does it need to be in, do I need to present to potential investors? Tommy
Andy Ayim
@tom_larder usually investors review pitch decks. You can find a template here https://blog.ycombinator.com/int...
Victor Khodalov
hi Andy! Very interested in product management and it's growth. What growth hacks would you advise?
Andy Ayim
@victor_khodalov I have a FREE mini-course on breaking into Product on Youtube: https://www.youtube.com/playlist...
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