Guest Interview: Adventures in Financial Independence

(Edition Number: Four)

Good morning,

Today, we are bringing you the fourth edition of the Investment Talk Guest Interview series, whereby I bring you some discussion with a selection of my favourite investors on the Fintwit hemisphere.

The gentleman behind Adventures in Financial Independence (ADVFI), was one of the first I connected with on Twitter. The community is truly powerful, and in a short space of time, ADVFI has already taught me a great deal about my own process.

What first lured me to his page, was the fact that he claimed to adopt the goal of turning a £40,000 loan into a £1,000,000 portfolio. Once I had read over his article which outlined the rationale and thesis for this journey, it resonated with me, and it has been valuable to watch the process unfold.

Adventures in Financial Independence (ADVFI)

I alluded to the £40,000 loan in the introduction. When you read the thesis for this journey, it makes perfect sense. ADVFI covers this in today’s interview, but you can find a brief overview of that here.

Documenting your investment process is something I am passionate about. Like last week’s guest, VSG, today’s guest is also a meticulous writer. The writings cover a wide array of topics from mindset to investment insights. ADVFI also posts fully transparent insight into his own portfolio each month, where he runs a fairly concentrated selection of SAAS companies.

You can find his work on his Substack (below), and find him on Twitter under the handle @adventuresinfi

ADVFI Substack

I personally read over each monthly update, and they are great. The real gold is found amongst the numerous and lengthy threads that ADVFI posts on Twitter. AS an active member of the community, ADVFI has even added value to my process during numerous discussions.

Prior to this year, I would state that my investing process was largely how I desired it to be, but my selling process was not. After a fairly simple discussion with ADVFI early in 2020, I left with a clear perspective, and shortly after drafted a document outlining my own ‘Rules for Selling’, which has benefited my mentality when considering selling positions.

I had discussed the sale of a PayPal position I had held for a number of years. After some back and forth, it appeared that I had no substantial or material reason for selling the position. That would have been a costly mistake, so I am grateful to today’s guest for improving my investing process this year.

ADVFI has also been busy producing content in 2020, and will shortly be releasing his latest project: “Losing in Order to Win: Secrets Behind $150,000 of Investing Mistakes”.

I am confident this is going to be a great bath of knowledge for anyone who is long-term orientated, growth orientated, is a buy and hold style investor, and is interested in reducing the likelihood and frequency of mistakes through the lessons ADVFI shares. You can find a link to this project, releasing in the new year, below:

Losing in Order to Win

Introductions over, let us now continue to the interview, which will be followed up with a selection of questions from Twitter.

The Interview

Investment Talk:

Hello ADVFI, I’d first like to thank you for accepting the invitation to partake in this interview-style newsletter, your time is greatly appreciated.  

First, I think it would be a great ice breaker, for some of the readers who may not be familiar with your work, if you could introduce yourself, perhaps detailing some of your background, what sparked the attraction towards investing, and take us through the sequence of events that led to you where you are today, and perhaps some flavour on the kind of work that you do. 


Hi IT and thanks for having me. It’s been good getting to know you in 2020 – definitely one of the positive things about the year. My parents immigrated to the UK in the 1980s and my father is a physician. Our family is originally from Nigeria. I work in the UK’s National Health Service, and used to be a management consultant focused on Technology Enablement in a Big 4 firm, often consulting to NHS Hospitals. Prior to consulting, I was a failed founder at an angel funded startup that had both the wrong team and unfortunate timing. I’m 41, happily married with 3 kids, a nice home, and all the external appearances of comfortable middle class life.

An old family friend had given me an investing 101 talk back when I was 15, and I was a university student during the dot com boom, so I’ve been aware of markets for a long time. I’ve always been a bit of a dreamer and a technology optimist - my first handle for my blog was NHS Dreamer before settling on Adventuresinfi. If you look at the bottom of my blog, it’s still copyright NHS Dreamer.  I had met a number of VCs during my Masters degree and when trying and failing to raise a seed round for our failed technology startup, so I became very interested in learning how they thought. I went to a talk by Reid Hoffman back in 2006 and was incredibly impressed by the way he looked at the world.

I started investing in July 2017 after taking a good look at the trajectory of our family finances, the cost of education, property, and my probable NHS income trajectory, which is currently around £64K per year and unlikely to get much above £91K. That sounds like a decent pre tax salary, but once you take into account the cost of living in the South East of the UK, consider the costs of childcare and education for 3 kids, and the fact that we still have £350K outstanding on a mortgage that runs for another 27 years, the freedom math goes against you quickly, even though the NHS pension is solid. I hated the idea of needing to wait till retirement age for financial flexibility. 

Something needed to change. Between 2012 and 2017 I’d made a number of throwaway comments that I had known enough in 2006 at Grad School to be able to see that $AMZN and $GOOG were obviously going to be great long term investments, and the $NFLX was an “obvious” call. My wife had replied

”if you’re so smart and think it was so obvious, then why don’t you have any investments?”

Investment Talk:

Everyone tipples on a different poison, and I feel investors should tipple with an investment style that best matches their own personality. So, how would you describe your own investing approach and why do you feel this pairs well with your personality?


I agree that investing needs to be a good match for your personality over the long term. I once had dreams of founding a multi-million pound startup that could do good in the world, so I’ve always been a fan of dreaming big and accepting the risk of failure. I have been a lifelong believer in the power of technology, progress, and asymmetrical opportunities. Although I was a failed entrepreneur, I realised I could back the people who were actually doing what I had once dreamed of with my capital and still participate in some way, backing successful entrepreneurs using technology to create a big impact.

I like to invest in things I can understand. Unsurprisingly, my portfolio is made of up of technology businesses in various forms. I understand the enterprise software space reasonably well, can see the organisational and secular tailwinds, and think SAAS is the best business model on the planet. As an example my interest and investment in ZScaler came when I moved to a different NHS organisation in 2017 where it was used to replace the previous VPN.  I have an undergraduate degree in BioMedical Sciences and “get” the impact of genetic technology and the impact of cost declines, and Wright’s law – some of the stuff that ARK innovation talk about quite a lot. It’s not hard to appreciate the increasing affluence of the Chinese consumer.  I studied technology management and innovation as a masters student at business school, so I like the idea of investing in subjects I’m passionate about.

Investment style wise, I like to think that my model is largely an approach heavily influenced by applying elements of the venture capital framework to public equities. I like to consider market, product, and team as key criteria for investment. I like consider my investment in “rounds”. I don’t mind paying up for de-risked or well executing companies and accept that market caps can increase rapidly in a relatively short time.  I like ideas with asymmetrical upside. Only the more successful VC backed teams make it to public markets. If you have a chance to make an investment in companies that are leaders in important emerging markets when the market cap to opportunity ratio is compelling, and you don’t have to take a board seat or help the company to hire – what’s not to like? Current valuations change the argument quite a bit though.

Personality wise, I’m fairly relaxed. I think it’s easy to spend time worrying about things that are either a) not under your control or b) do not matter. A lot of things you can devote mental energy to don’t really matter and won’t make a difference to your life a month down the line. 

I try not to do that and try to optimise for what is under my control. I am a big believer in optimising process over trying to optimise outcomes and put a lot of energy in to trying to learn how to make better decisions.  

Investment Talk:

You have a very interesting mission. In your own words, you are aiming to turn a £40,000 loan into a £1,000,000 portfolio through the stock market. Talk us through why you opted to use a loan as your initial principal, and if you could talk about how that impacts your investing decisions on a mental level, that would be great. 


I was late to investing. The biggest benefits of compounding come are much more apparent the higher the capital base. Charlie Munger himself said “The first $100,000 is a b*tch, but you gotta do it”
So the question becomes how to you get to the first £75,000?

Outside of the mortgage, we had low consumer debt and a good credit score. I had £20,000 in savings that I had wanted to use for investing, and we were priced out of considering local property as an investment opportunity.

Back in 2016-17 I had a temporary reduction of about £500 a month in take home pay. It made life tricky for a few months, but we adjusted to make things work. When the situation was resolved, it crystallised the fact that that there was an opportunity to invest that £500 a month in order to get money working for us. 

Taking the long term view, I decided to consider the next 7 years which would take me to my mid 40s:

£500 a month x 12 months x 7 years takes you to £42,000…That was the beginning of the idea. I thought – what if I inverted the process, and started with the £40K at the beginning of the 7 years through a loan and used the time to pay it off while letting compounding work for me instead? I’m pretty good at my job in the NHS and it’s pretty secure. So if you know you can afford the payments, why wouldn’t you invert the process? The ability to pay the loan was not dependent on the investment performance. The risk of ruin was within my tolerance. I accepted it would be a steep learning curve and I was willing to put in the work. I took out two loans, one with M&S Bank for £15K another with Tesco Bank for £25K. The payments were £185 and £330 a month respectively, so £515 a month. I’ve paid off the M&S loan in full, and there is about £16K left on the Tesco loan at £330 a month.

Investment Talk:

I recall some time ago; I was pondering selling my PayPal position that I had held for a number of years. After a discussion with you, I realised how whimsical my rational for selling was. I found that conversation, although brief, to have stuck with me. If you do not have a great reason to sell, then why would you sell?

If you could take us through some of your insights into what would lead to you sell a position? Feel free to refer to the below chart, as I will be including it.


My biggest insights have come from my own biggest mistakes. I’ve tallied up the cost of my investing screw ups, based on information that I knew at the time that I made the decision. My investing errors have cost me over $150,000. The most costly errors have come from selling shares of companies I believed in and were executing very well, and were still at an attractive market cap to potential. Selling winners means that you miss out on the benefits long term compounding.

So for me, the main reasons to selling come down to whether or not I believe the company remains a good place for my money – things that damage that belief typically come down to a broken  or damaged investment thesis, loss of trust in management, discomfort with position sizing,  alternative needs for the money or a phenomenally better opportunity elsewhere.  Boredom, short term thinking or “it’s gone up” are not good enough reasons, as I discovered from first hand experience.

Investment Talk:

You are very open with your investments, which is something I admire. Your wins, and your losses are each up for discussion and disclosure. Failures are a painful way to learn, but an effective one all the same. 

What have been some of your largest mistakes in your investing journey, and how have they shaped the investor you are today?


Thanks. When I was new to investing, I had some early successes. In my first year of investing I bought shares in Shopify, Square and The Trade Desk. I was overconfident and didn’t realise how far to the left of the Dunning Kruger curve I was.  

In my first 2 and half years as a n00b, I made an impressive set of screw ups. I’ve bought penny stocks, value traps, sold winners way to early, bought companies too soon after IPO, gone all-in just before ER,  over traded and bought on FOMO.

It wasn’t really until summer 2019 that I took the time to really work on what I think every investor needs – my investor policy statement. I went forensically through my brokerage statements, analysed my behaviour and decision making and realised I need to add much more structure to what I was doing. As I mentioned – I realised my mistakes were getting expensive and that also compounded over time.

 It was funny – in my day job, I take a lot of pride in consistent, structured decision making and was very used to breaking jobs down into processes and optimising them. I realised I needed to do the same with my investing, and become much more intentional with my behaviour. I really had to nail how I made buy, sell, and hold decisions, what type of companies I was looking for, what my philosophy was, and how my strategy would fit with it. As a result of my screw ups, I think I’m a much better investor now. But it is expensive tuition.

I’m in the final stages of putting together an online course based on my greatest failures, where I break down in embarrassingly painful detail exactly where I went wrong, why I did what I did, show how much the mistakes cost me, and give tools and strategies for new investors to avoid making the same mistake and wasting their time and money. My hope is that people can learn from my n00b screw-ups without having to make them themselves.  

Investment Talk:

Which investors, past or present, or even mentors outside of the investing space, have had the most significant impact on your own approach? 


My parents are the most inspirational people I know. My father walked miles every day to get a good education, worked hard all his life and got scholarships. Both my parents survived civil war and moved their young family to different countries more than once in order to provide a better future despite incredible challenge and adversity. He and my mother provided financially for 5 children and helped fund the education of many of their nieces and nephews, as well as countless other relatives back home in Nigeria. Dad could retire tomorrow if he wanted to but enjoys his job as doctor. My mother sacrificed her high flying career to enable her family to have a better future in a different country. Both my parents have a level of resilience, spirituality, generosity of spirit and gratitude that I aspire to.

Investment Talk:

I am a huge advocate for considering your library as an asset. Some of my favourite books, which I often go back to, are: The Intelligent Investor, The Innovator’s Dilemma, Stress Test, The Dark Side of Valuation and Common Stocks & Uncommon Profits. 

If you had to choose three books, of any genre, that you found either; changed your outlook, or were just fun reads, which would you chose and why?


The Innovators Solution – For understanding disruptive innovation, understanding the framework of “jobs to be done”, the concept of “good enough”,  emergent strategy, the importance of the ability to learn over track record

Diffusion of Innovations by Everett Rogers – for deeply understanding what characteristics make an innovation successful and for understanding the difference in markets. Geoffrey Moore’s Crossing the Chasm takes these frameworks and applies it to Technology with a few modifications of the Chasm, so that’s an alternative

Common Stocks and Uncommon Profits is the best investing book for the investors in fast growing companies and is as relevant today as in 1960

My favourite book this year is Alchemy by Rory Sutherland – it explains a lot of the apparent absurdity of life.

Investment Talk:

I like to ask all guests this question. Concentration in high conviction positions is one of the most efficient ways to earn outsides returns. However, it can also be an excellent way to blow up your account. What is your take on position sizing, or allocation in general?


It’s a very individual decision. We are all wired different. I think investors need to be intentional with their investing. What makes perfect sense to one person looks like lunacy to another.  I know I can realistically monitor up to 15-20 companies well to a standard I’d feel happy with, so that’s the approach I take.

I currently have 12 companies in my portfolio. I think about position size at the point of capital allocation and won’t invest more than about $10,000 in any single idea. That’s a number where I can cope if it get cut in half but also where a 2x would be material. If you’re right more than half the time, you’ll be ok. I buy in stages, and am comfortable adding up. If a position grows to be a large part of the portfolio, that is a feature and not a bug or a reason to trim. It’s probably doing well because it’s a good business – if you sell what are you really achieving?

Investment Talk:

You often discuss the wild swings that a portfolio, with as much concentration as yours, can have. The stomach is sometimes as useful as the brain when it comes to investing. I like asking guests what they think about the idea of a portfolio that allows you to sleep well at night. 

What is your take on that philosophy? Moreover, how do you deal with holding volatile positions such as the ones you hold?


If your portfolio messes with your sleep, you are doing something wrong. Figure out what it is and change it.

I personally try to avoid making many investing decisions. I now default to intentionally “doing nothing” unless I feel compelled to do something. For me to break from “doing nothing”, something special has to be up, and frankly, most companies aren’t that special. Companies are not just the stock ticker -  I spend a lot of time analysing the businesses I am interested in or invested in. Having a good knowledge base of what I own makes me far less concerned about short term swings. It’s the long term that interests me the most. Volatility is part of the “fee” for investing and should be considered as such. If that bothers an investor, they need find a strategy that matches their personality. 

Investment Talk:

What are some of the areas that you feel will be most disrupted, or perhaps shown the most promising disruptors over the next decade, and why?


Great question. I think that healthcare is the most interesting area for the incorporation of technology, but I’m also sure it’ll take longer than anyone expects. I’d like to see a world where doctors, engineers, hospital administrators and entrepreneurs can collaborate and innovate in a pragmatic way that gives permission to fail and scope to iterate. 

Investment Talk:

Another question that I like to ask every guest. There are three variables that exist in investing: luck, skill, and mindset. Of course, there are more variables, but what is your opinion on the relationship between these variables, and to what extent would you say each is important?


Mindset come first. You have to be willing to challenge convention, take your ego out of it, accept the risk of failure and have resilience to adversity. Skill is important because you have to learn how to get good and have an idea of what that looks like. The stronger your mindset and the better your skills and processes, the greater the surface area for good opportunity. Luck is always welcome, but you can’t rely on it.

Investment Talk:

Lastly, my favourite quote, comes from Graham. The one concerning the short term voting machine and the long term weighing machine. I find it helps me reconcile the irrational price action in the near-term. I do not know who first coined it, but another of my favourite quotes is “If you don’t laugh, you’ll cry”. I find this quote helps me appreciate the randomness of life and the lack of control we have over external factors. 

What is your favourite quote, and why?


Two spring to mind

Martin Luther King

“The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy.”

Theodore Roosevelt

"It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat."

Questions from Twitter:

In this segment, we collected questions from the Twittersphere, and present them to ADVFI.

@fradeduarte: “European growth stocks, any good ideas?”


Elastic – it’s on the NYSE but is definitely European (is that cheating?)

@1steptrader: “What was your trading/investment experience before deciding to use a loan to fund your account?”


Minimal direct experience. A lot of learning through entrepreneurship and trying to getting into the minds of VCs. When I was a grad student, I spent a lot of time looking through the ER reports of Google and Amazon though.

@chaturavi: “Which portals to use for Fundamental Analysis?”

ADVFI:  I like,, 

I have a blog post that might help 

Link to Blog Post

@IrnestKaplan: “When you took out the loan, how long did you think you would pay it back over? Has it been faster? What interest rate is the loan at? Would you borrow a bit more now or is that it?”


I took two fixed repayment loan for 7 years at 2.9%. I’ve broken the monthly payments down earlier in the interview – there is about £16K left to pay. I have no desire to increase the amount borrowed as I think that the risk reward with current valuations skews away and I am not greedy. You’ve got to know when to go for opportunities and when to sit back and avoid unnecessary risk. The job of the loan was to get to that first $100,000 faster. That job is done, so the rest is down to more conventional methods. 

@PaulH_11:“As a UK investor in global stocks /ETFs (mostly USD), how can you protect your portfolio from FX risks of a weaker USD?”


This is a great question and not one I’ve ever given much thought to as my portfolio hasn’t been large enough for it to be a real consideration. I think that the best hedge is to buy great companies and not worry too about things that are outside your control. Currencies will fluctuate, and I’m not sophisticated enough to give you a clever answer, but my friend Finumus is:

Finumus Article

@TJ_Osterman:“What’s your number to consider yourself truly financially independent and how’d you roughly arrive there? Thanks!”


Truly independent would about £2.5M

@JamesThom07:“If you were starting now, with the current market and some overextended stocks, would you still leverage via a loan? Or wait for some sort of pullback in the markets?”


I would not do it today – I can’t see the asymmetrical opportunity with current market madness. 

@GrowthStocksRock:“Why do you think it’s so hard for mutual/equity funds to do so? Is it volatility= risk mentality?”


I imagine once you are managing OPM (other people’s money), the incentives are very different. Your career risk is a big challenge, the client risk profile breadth shifts, you have to persuade whoever holds the wallet about the merit of your ideas, and you have all kinds of fund rules about sector exposure and portfolio allocation – you will likely be forced to trim winners and invest in the known, even if the rewards are not asymmetrical. I think it’s largely down to incentives, but as I have never worked in the field, I don’t know for sure.

Before we round this interview off, there was one question that was hot on everyone’s lips when I initially asked Twitter to send me questions for our guest today.

I can reveal, that ADVFI’s profile photo, was taking from Jervis Bay, Australia!


That wraps up today’s guest newsletter, which marks the Fourth edition of this series. I want to thank AdventuresinFI for taking the time to answer these questions today. I find his wisdom to be calming.

The concept of using a loan to finance a portfolio is a topical one. I was most interested when I first reached out to ADVFI because that is something that I would certainly do as well. The rationale is strong in my opinion. Just because it is not conventional, does not make it wrong. I admired that.

Stay tuned, as we have some excellent calibre guests lined up for you in the coming weeks.

You can find previous editions of the guest interview series below:

• Edition One: Bill Brewster

• Edition Two: Kris FromValue

• Edition Three: ValueStockGeek

• Edition Four: AdventuresInFI

• Edition Five: Brian Feroldi

• Edition Six: Brad Freeman

• Edition Seven: Mostly Borrowed Ideas

• Edition Eight: Richard Chu

• Edition Nine: Kermit Capitál

• Edition Ten: Liviam Capital