A framework for making important decisions: Step 2/4

The process of putting your thoughts on paper is useful as it crystalizes your thinking and may allow your subconscious mind to come up with the right answer in the days, weeks and months following your email to yourself. Step 2 allows you to further refine your thoughts and accelerate the process of coming up with the right answer for you.

Step 2: Get your close friends, mentors and advisers’ opinion

The email to yourself is a great starting point for a productive conversation. I send it to my friends, mentors and advisors and ask them to tell me what they would do if they were me and what they would do if they had to make the decision.

Many of these conversations happen in person, but I found that some of the most productive ones happened iteratively via emails with my more thoughtful friends. Honestly their advice has rarely turned out to be directly applicable or useful given how different we are as individuals and in terms of what motivates us. However, the iterative process of talking through the various is options is tremendously helpful. It helps us consider angles we had not reflected on, narrow down options and generally further our thoughts.

In my case the most useful conversations have been with my friend Ben Lee whom I met at Princeton. He’s extremely introspective and thoughtful and I highly value his insights and questions.

Here are a few examples of our interactions color coded for the sake of clarity. They are far from exhaustive because we would reply on top of replies dozens of times for many of the individual points leading to real depth and analysis but give you a sense for what we discuss. My comments are in red.

From: Fabrice Grinda
Sent: Saturday, August 4, 2012 7:16 AM
To: Benjamin Lee
Subject: RE: Thoughts on what I should do next with my life…

Comments below.

On Mon, Jul 30, 2012 at 11:21 PM, Fabrice Grinda wrote:

1. Leave OLX

In terms of tax optimization is London is that good in terms of taxes? I thought Branson tries hard to keep his companies out of there? Btw, you are still a French citizen?

I am still a French citizen. London is not great for British citizens or for people who earn their income in the UK. No country is great for US citizens or green card holder because they must pay US taxes on their global income no matter where they live. However, the US is one of the only countries to impose that. Citizens of all other countries pay taxes where they live. As I have been a US tax resident for the past 20 years, I pay US taxes on my global income the same way an American would which amounts to something around $25 million for the past few years.

The UK is great for French citizens. The UK taxes your income in the UK at 45%, but your income outside of the UK is not taxed. Given that most of my income comes from the sale of non-UK startups, I would have paid a maximum of $1 million in taxes over the same period. It’s a HUGE difference.

Now, I love New York and the opportunities that the US has given me, so I don’t mind paying some taxes. The issue is that I foresee tax rates on people like me only going up in the future in the US. I don’t mind paying 25%, but I am not keen to pay 50%. When I started capital gains taxes were 15% federal + 7% New York State + a 3% New York City. Now it’s 19.6% + 9% + 4% and going up… That’s why I never got a green card. I wanted the option of leaving to remain open. In the case of my put on my remaining OLX shares for instance, if I lived in London when I exercised it, I would pay 0% / $0 on the proceeds of the sale.

Given my lifestyle choices where I spend so much time on the road, I actually could already qualify as a non-US taxpayer. I just think it’s fair for me to be paying US taxes while I am notionally based here. We’ll see going forward. That said I have no intention of living my life to maximize my after-tax returns. I just want to maximize my productivity, happiness and wellbeing.

2. Try to convince Craigslist to let me run them

I would think this to be highly unlikely. Buckmeister is a fan of Chomsky. If he does even the slightest bit of background checking on you, he’ll hate your guts. Unless you can somehow bypass Buckmeister, you have no chance whatsoever.

Possibly but Craig refuses to engage on anything business related and just tells me to “speak with Jim” so there is no choice. I realize that Jim and I are fundamentally different, but that does not mean I could not help save / transform / grow their business which he may appreciate. The issue is that I suspect he does not care about the business. Anyway, we’ll see. Shockingly no one in my network seems to know Jim. He’s not on Linkedin. He has not tweeted in years and he did not reply to my email…

3. Try to extract the non-strategic countries out of OLX to have a dividend stream + try the classifieds 3.0 strategy

This sounds interesting, but what is Classifieds 3.0? I seem to have missed that somewhere. With your references to web 3.0, do you mean the “semantic web” which was all the rage several years back? Or are you talking about some other conceptualization of web 3.0?

In terms of classifieds, it’s really something I came up with imagining a re-invention of existing sites using the latest trends and technologies in the Web writ large.

  • Have a mobile first experience based on mobile apps using the capabilities of smart phones:
    • Super simple photo-focused listing process
    • Geo localizing the seller and the items
  • Transaction and/or advertising business models instead listing fees
  • Search results organized by relevance and location in addition to posting time rather than by latest postings first
  • Full transparency on the buyer and seller with forced Facebook sign ins and profile import instead of anonymity
  • Built in scheduling of appointments in the case of things like baby sitters, etc.
  • Optional buyer paid closed loop transactions through an escrow service where the buyer pays the site and the site pays the seller rather than free form offline transactions
  • Individual rating system for those who have completed closed loop transactions
  • Integrated social transparency to increase trust -> you see if friends, friends of friends, classmates or fellow workers have interacted with or know the seller or buyer
  • Optional pushing of your activity to the social web, especially Facebook, Twitter, Pinterest and Tumblr

Note that it’s important that the transaction fees be low (say 5%), optional, and paid by the buyer who choose to use the escrow service for convenience and safety. It can’t be charged to the seller otherwise they might prefer to stay on the incumbent free platforms like Craigslist despite the worse user experience.

Regardless, Naspers is not quite ready for that yet. I need to continue warming them up to the idea.

4. Think through the new idea I should build or company I should run

I think a startup may be the most productive use of your time. I continue to believe you’re a better founder than angel investor. However, on the downside, I’m not sure there are as many easy ideas out there for the taking as there were during the early days of the web.

Who got the followup email on justanswer.com?

We’re working on a deck, interviewing Just Answer experts, etc. Given how much money they spend we need to think through ways to increase NPS / repeat usage otherwise we won’t be able to compete effectively.

5. Find the next thing to incubate – possibly a Viajanet for Indonesia and South East Asia

I never understood why startups like incubators. Maybe it’s because I would never use one and would be less likely to invest in a startup that used one. If the startup founders feel they need to be in an incubator, are they really tough enough to succeed? I would guess incubated companies can be moderately successful, but I have my doubts about them hitting any home runs.

Especially in more conservative societies and places where entrepreneurship is less prevalent, the incubator model has worked reasonably well because:

  • We remove the entire burden of fund raising from the team (and it often takes a huge % of their time)
  • Given that we give them $4 million and 40% of the equity, it’s not much less than they would have had if they had raised a love money round, a seed round and a series A round plus the creation of a large option pool
  • We bring the founders online expertise they don’t have, especially in customer acquisition

I think this can be a $100 – $1 billion business and that I can get 10% of it in sweat equity.

6. Keep angel investing in the most interesting / attractive projects

As you know, I have limited faith in the near term future of angel investing. I know you enjoy it, and I agree that it’s a nice way to keep your ear to the ground (which is one reason I enjoy being on your angel email list).

In terms of your angel success rate, Buffett used to say he goes around looking for the stock market equivalent of cigarette butts with one puff left in them, as people are willing to give them away. I would think angel investing has some similarity there, and that’s why you’re able to pick up companies hitting singles and doubles at a decent price. Or at least you were able to before the current insanity started.

What’s interesting is that the current insanity is helping us get exits. It may not appear that way to you, but we are being much more careful. I invested significantly less this year than last year – essentially dividing my check size and the number of companies I invested in by two. I am writing a big check in Mindbody which will increase the amount invested, but it falls in a different later stage category.

I would be cautious of trying too hard to hit home runs by investing in “crazy” ideas. Your skill set isn’t well matched, and I’m thinking it’s more likely you’ll endure a series of strike outs.

I hear you. I don’t intend to do many of those.

7. Try to buy the IP for Rise of Nations

Really interesting idea. I’m not sure it will be financially worth your while, but I’m assuming your finances are sound, and it could be a really neat project to do while waiting for a new startup idea or for the angel investing world to cool down again.

I have no expectation of making money on this. Also, Kickstarter is revolutionizing funding for hardware sales and I suspect will help people fund projects like this one in the future.

8. Become a credible public economic commentator

Jumping ahead for a moment, one of the major problems you may face with politics is you have a blog. In fact, I’d guess you’ve pretty much ruined your chances for any major political office already based on what you’ve already written on it to date. I’m unlikely to run for public office, but there’s a chance I may someday try to be CEO of our radiology group, and even in that role, it’ll probably be better not to have a significant “paper” trail.

An appointed advisory position is obviously different, and the blog won’t be as much of a problem for that. However, I’m not sure how you would go about getting such a position without either going into academia or becoming the CEO of a financial institution?

I wonder as well. I toyed multiple times with getting a PhD in economics at Cambridge, Princeton or Oxford. All three have “part time” programs, but I could never quite justify the opportunity cost of time. This one is more of a “nice to have” than a need to have. I will continue pontificating publicly and trying to get the word out. If it works great, but if not, not huge loss.

I also wonder if it would not be healthy to make a clean break and take 6 months to a year off just to recharge and clear my mind.

In a way, I feel like doing the rise of nations 2 project might be the perfect recharge. Yes you’d be working really hard, but on something you really like that is quite different from what you’ve been involved with before. And you never know whether something like that could end up being your greatest long term success story…

That’s true! We’ll see how the bankruptcy plays out. The timing and potential bidders for the assets are still completely up in the air.

Spend some time going to see my closest friends wherever they are in the world to spend quality time with them.

I applaud the concept. I probably won’t get a chance to do something like that until the kids are much older, but I hope you do it at some point in your life regardless of what path you take next.

I think I might do that anyway in the next year or two regardless of the path I take.

The annoying thing from this list is that most elements depend on third parties -> Rise of Nations, the put, extracting irrelevant countries from OLX and Craigslist all require someone else to agree to my idea.

We’ll see how things play out in the next 6 months.


A framework for making important decisions: Step 1/4

In life there seems to be a pretty clear default path in terms of societal, parental and personal expectations: go to college, get a job, get married, have kids. In addition to the default general path, there is a default choice for each of these: continue doing whatever it is you are doing. The easiest thing to do is to stay in your current job, live in your current city, in your current apartment, with your current significant other. Time spent in a default position seems to create a momentum of its own on that position across all categories.

The reality is that we are generally lazy and don’t take the time to question either our general life direction or the specific choices within that direction. Yet, many of these results come from happenstance or circumstance.

The last thing we want is to wake up late in life realizing we have been running in the wrong direction. Because we are so busy living on a day-to-day basis, I find that it’s important to take the time to take a step back and be deliberately introspective about life’s major decisions. To do so I created a process and framework for making these decisions.

After several iterations, I came up with a process.

Step 1: Assess in writing where you stand and the options available to you

We usually have a vague sense of pros and cons of various options in our mind, but I find that’s it’s extremely valuable to write them down. The process of writing down an analysis of your frame of mind helps you crystallize your thinking and make the options much more explicit.

I typically start with an evaluation of my current mindset in the default position and weigh the pros and cons of staying in that default position. I then generally lay out a set of different paths. In doing so I found it best to follow a few rules:

  • Be as open and honest with yourself as possible in terms of assessing your frame of mind
  • Don’t put any limitations on the paths you could explore and force yourself to include highly unlikely and difficult things
  • Don’t try to reach a conclusion in the email to yourself. Laying out the options and their pros and cons is enough. The answer will come in the following days, weeks or months
  • When evaluating alternative paths be careful to imagine yourself on a typical day and not an idealized version of that path

Sometimes there are clear points at which you should write this email to yourself because you are facing an obvious important life decision:

  • You are hesitating between several jobs to take
  • You are wondering whether you should propose to your girlfriend
  • You are considering selling your company
  • You just sold your startup and are wondering what to do next

In a way those are the easiest times to take a step back and be introspective because there is a clear life break. However, because of the power of momentum, it’s essential to do it when there are no such obvious breaks. I would recommend doing it whenever you feel a general sense of malaise in life.

Evaluate how happy you are in your current life relative to what you used to be or would like to be and assess if there are changes you should make. Sometimes you are not even aware of said malaise which is why it can be good to force yourself to write this assessment at artificial points in time. I either do it on my birthday or at the beginning of the new year at the very least once every other year.

Here are a few examples I wrote to myself in different contexts. In The Power of Introspection and Detached Analysis, I shared the email I sent myself in January 2001 when evaluating what to do after I had (badly) sold my first startup, Aucland. I was 26, the Internet bubble had burst, and it seemed liked the Internet was dead, or at least was not going to be something big. I had been at the right time, at the right place, with the right skills, and left a unique opportunity in life pass me by. I raised tens of millions in venture money and employed hundreds. I had been on the cover of every magazine and newspaper in France. I was featured on popular TV shows, and was generally publicly recognized as a disruptive entrepreneur, before it all very publicly came crashing down. I had soared to great heights and wondered what lay ahead, what path to take, and whether anything would ever feel so magical again.

I also share below an email to myself right before my birthday in 2012. This one was written from a very different perspective. I was already a successful Internet entrepreneur and angel investor with numerous exits. I was co-founder and co-CEO of OLX. The company was super successful, an amazing platform and a tremendous source of meaning given its societal impact. I was also publicly lauded and recognized for my work. However, I could not shake the feeling that something was off. As such, I wrote myself an email laying out what seemed unimaginable, leaving a position of power, respect, meaning and opportunity, because the day to day was no longer palatable.

From: Fabrice Grinda
Sent: Monday, July 30, 2012 11:15 PM
To: Fabrice Grinda
Subject: Thoughts on what I should do next with my life…

I have been putting some thought into where I stand in life and what I should focus on over the next year. I came up with 8 objectives.

1. Leave OLX

OLX is really the company I envisioned running for the rest of my life. It seems paradoxical to consider leaving OLX now that we have succeeded. We have hundreds of millions of unique users per month. We are the largest classified site in countless countries. We are making a meaningful difference in the lives of millions of users. Receiving thousands of love letters from users every day is a source of pride and meaning.

I also don’t underestimate the value of having a platform with hundreds of millions of users. It’s an amazing launchpad for new verticals and ideas. Every test we do is statistically significant. Investors keep telling entrepreneurs to multivariate test everything, but the reality is that unless you have the traffic to meaningfully test everything, it’s hard to make informed decisions. With the traffic OLX has we know within an hour if an idea is going to work. With this traffic level, disruptive product change can be 1% improvements done 1,000 times over.

So why leave? The reality is that the nature of work at OLX has changed now that we are part of a large publicly traded company. Partnering with Naspers was the right bet. When Naspers approached us in 2010, we realized that the business was essentially a natural monopoly on a national level and that we had to be absolute leaders in a few strategic countries. To withstand the onslaught of Schibsted and well-funded competitors like Quikr in India, it made sense to get the support of a deep pocketed strategic backer.

Naspers has proven to be a fantastic acquirer. They are the very opposite of the Japanese who had acquired Zingy. They are strategic, thoughtful and incredibly aggressive. I was pleasantly surprised and sometimes downright frightened by their aggressiveness, which is saying a lot given that it’s in my nature to be very aggressive. I can say with confidence that we would not be where we are today had it not been for Naspers investing.

We put the money they gave us to good use and won the war over the last three years but had to lose our independence to do so. While I have tremendous pride in what we have accomplished and love the recognition I get as co-founder and co-CEO, I no longer love the day to day job. When I built OLX with Alec, we never talked about who would do what. We have overlapping skills being Ivy League educated consultants and auction site CEOs and each can do the work of the other. The role split happened automatically driven by our interests, geographic location (him in Buenos Aires and me in NY) and lifestyle choices.

I ended up overseeing the product strategy, investor relations, front line M&A (identifying and reaching out to targets), business development and English PR. He took the lead on operations, post-merger integration and Spanish and Portuguese PR. We both jointly set the strategy.

It has often been said that it’s a bad idea to have co-CEOs and work with friends, but when you can make it work it’s much more powerful. You have a level of trust that does not exist in traditional business relationships. We never argued or disagreed, and our friendship has never frayed. Likewise, I am still close friends with William and Ariel despite working with them for many years.

Post-Naspers investing, the nature of my work started changing. I no longer had to manage investor relations. The M&A and business development roles disappeared as we started focusing on organic growth. Simultaneously, we started needing to have a structure and budgeting rigor commensurate to our size, not to mention being owned by a large publicly traded company. We now must create detailed annual budgets, quarterly budgets and updates to the quarterly budget, and make sure we hit those numbers. Our decision-making process is no longer an (hopefully) enlightened dictatorship as we need to get shareholder approval for strategic initiatives.

All that to say, that I am not loving the day-to-day. I don’t think OLX needs two co-CEOs anymore. Frankly Alec is better temperamentally suited for managing a shareholder and organization like Naspers’, while I find myself yearning for a new adventure.

Next step: Talk to Alec and Naspers.

2. Try to convince Craigslist to let me run them

Craigslist has 30 billion page views per month. If I was running it, I could both improve content and site quality dramatically and make it relevant for the 21st century. Craigslist has the potential to be a $100+ billion company given that it has liquidity in so many valuable categories. However, as it is, it is profoundly flawed. Women are the primary decision makers in all household decisions: which house or car to buy, what babysitter to hire etc., yet Craigslist is the least female friendly site in the world.

They should take a page from OLX and pre-moderate all content before it goes live to make the site spam and scam free. They should remove personals which make the site creepy. They should build a delightful mobile experience and redesign the site.

They should also change their business model to replicate OLX. Classifieds are a wonderful business that can have upwards of 75% EBITDA margins and you don’t even need to charge listing fees. They charge listing fees because they are too lazy to moderate the site. For them it’s a form of spam control, but it also limits liquidity in certain categories. Even by going 100% free and hiring 1,000 people to moderate the site, I could easily make it generate several billion (yes with a b!) in profits per year.

My pitch to Craig is as follows:

  • I share your vision of providing a public service to the community
  • You could be doing a much better job by improving content and site quality
  • You don’t necessarily want to do the work, but I am happy to do it for free
  • Just give me 3% of equity / year worked. The equity vests after 1 year so if you are not happy with my work just get rid of me on day 364 and I cost you nothing

I had a quick chat with Craig about the future of classifieds (and did not pitch myself for the job). He told me to speak to Jim who is CEO and introduced me. I told Jim I was going to be in SF and would love to meet for a quick coffee. I was not going to be there but would have gone had he said he was available. He did not reply. I also sent him a follow-up email to which he did not reply.

I will forward the email I sent him to which he did not reply.

Next step: Find people who know Jim Buckmaster well and convince them to have him meet me.

3. Try to extract the non-strategic countries out of OLX to have a dividend stream + try the classifieds 3.0 strategy

Those countries generate $7.5 million in revenues and $5 million in profits per year for OLX, yet Naspers has repeatedly asked us to close them.

They obviously don’t want me to get them for my own purposes, but I am trying to convince them that they have no real strategic value and as such we should try to build a next generation classifieds 3.0 site which is the only way to have a shot of being relevant in those countries

To do that effectively, we would need to spin it off as it would require a complete product redesign to a mobile first (and perhaps only) experience, with a super simple photo-focused listing process with an optional buyer paid payment and escrow solution.

Next step: Pitch the idea to Naspers in the coming months.

4. Think through the new idea I should build or company I should run

I thought long and hard about creating a VC or angel fund. The issue is that fund economics only work if you have several hundred million under management. Moreover, each fund has a 10 year life which is a huge time commitment. I tend to get restless before then. The way it would have worked would have been as follows: raise a $50 million fund, raise a follow-up multi hundred million fund in 3 years and another one 3 years later. In other words, it’s at least a 16 year commitment with a lot of administrative / boring work in terms of raising money from LPs, doing reporting, etc.

I am also not sure it’s something I really would want to do full time. I have been meeting VCs and PE firms to discuss:

  • Which of their portfolio companies I could run
  • Which public companies we should take public and have me run
  • What are the hot trends / companies to see if there is room for a competitor / differentiated version of the idea

I am trying to move away from mere idea arbitrage:

  • It’s harder if not impossible to build $10+ billion companies outside of the US
  • I don’t really want to travel as much as I am currently traveling
  • I am less effective managing a product and technology team remotely than I am when they are right next to me

The conversations have been interesting and I was approached to be CEO of a few publicly traded companies which is ego boosting. However, there was nothing as appealing or interesting as being CEO of Craigslist.

I explored a lot of categories in terms of new ideas to build. I spent a lot of time on 3D Printing, which will be a huge category, before deciding not to pursue it. I also considered bringing www.made.com to the US, before also discarding this idea. I am happy to explain why in more detail.

The one idea that has bubbled up and that we are exploring further is building a next generation version of www.justanswer.com. Shockingly the company is on a $150+ million revenue run rate. Given how much of the economy is in services and information, this has the potential to be extraordinarily big if done right. Moreover, the unit economics are nearly as good as the one in stock photography which has not proven to be a winner take all business. I will send you an email on that category.

I am doing a lot of research right now into Just Answer: interviewing their customers and experts, trying to figure out how much liquidity they have in each category, thinking through what product improvements could be done, etc. We’ll see where I end up falling on this.

Next step: Keep studying the model.

5. Find the next thing to incubate – possibly a Viajanet for Indonesia and South East Asia

Some of the clear lessons of the past few years of angel investing and working with Jose on incubating companies in Brazil are:

  • Travel is a huge category
  • Incubating a company allows you to have a disproportionate share of equity for very little
  • A few companies generate most of the returns

Based on recent market analysis, there seems to be a clear opportunity to build an Expedia for Indonesia and possibly all of South East Asia. We are currently evaluating the market:

  • Interviewing CEO and cofounder candidates from various business schools and people with travel background in the region
  • Talking to various travel wholesalers

Next step: Go to Indonesia September 3-7 to meet all the potential cofounders and partners.

6. Keep angel investing in the most interesting / attractive projects

I invested in 105 companies over the last few years and evaluated over 3,000 projects. I actually loved meeting all the entrepreneurs, hearing their ideas, figuring what was hot at any given point in time. Beyond the sheer promotion of entrepreneurship which is valuable in its own right, the process is informative in terms of understanding larger trends to better decide what projects to incubate or start on my own.

Interestingly enough, so far we seem to have been good at selecting logical projects that have earned good returns. We have the best win – loss ratio of any angel investor or VC I know with 14 wins for 7 losses. However, none of the winners have proven to be home runs. In other words, we seem to be great at picking companies with good on base percentages which hit singles, doubles and the occasional triples, but we have not been good at finding disruptive winners. In a way we are attempting to assuage this limitation by investing more in “crazy” ideas from US companies instead of just investing in international idea arbitrage businesses.

One potential idea for scaling this part of the business might be to pitch Naspers on running a $100 million angel / series A investment fund for them should they accede to giving us a floor on the put.

Next step: Continue meeting companies, being more vigilant about our investments given the frothy times in angel investing, yet trying to be open minded enough to increase the probability of home runs.

7. Try to buy the IP for Rise of Nations

This is more of a “love project” than anything. Rise of Nations is my favorite strategy games in the history of strategy games. It mixes the real time gameplay dynamics of Age of Empires, Warcraft, Starcraft and Command & Conquer with the strategic and tactical depth of Civilization. Big Huge Games, the company that developed it, stopped focusing on this IP 9 years ago and instead started building role playing games. Their huge bet in the category recently failed and the company filed for bankruptcy in a very public scandal. There is currently a legal discussion over the jurisdiction of the case. Once it’s settled, I would like to try to find a way to buy the assets for cheap with the intent of building Rise of Nations 2. It would simply be a multiplayer version of Rise of Nations 1 with updated graphics and the tactical unit control of a game like Company of Heroes. I would try to get it funded through Kickstarter.

Next step: Bid on the Rise of Nations IP once it’s for sale.

8. Become a credible public economic commentator

I had political ambitions growing up and still spend a lot of times interacting with people in think tanks and various thought leaders. However, I am starting to feel as much apathy, if not antipathy, for the body politic as Peter seems to feel given his comments in the New Yorker article. I agree with him that Rand type entrepreneur can have more impact on society.

That said, post our conversation, I am starting to think that an appointed position like being on the council of economic advisors to the president would be interesting. Unfortunately, the world approves and rewards specialists rather than generalists. I get no credit for predicting the financial and real estate crisis. In order to get more visibility and improve the chances of such an appointment, I reached out to Nouriel Roubini, Paul Krugman, Niall Ferguson and Matthew Bishop (the editor in chief of the Economist for the US) asking for their ideas on how best to promote the ideas.

I put a fair amount of thought about how to engage them to maximize the probability of a reply. Unfortunately, they have not replied yet. I will send you some of those emails.

Next step: Keep approaching thought leaders and pitching them my ideas.

Other considerations:

Many of the 8 priorities are mutually exclusive. Should I get the CEO role at Craigslist, I would essentially drop everything else given how big that opportunity is relative to the others. In that context I would not mind completely stopping angel investing and incubating startups. I do it because I find it interesting, I love promoting entrepreneurship, meeting hungry entrepreneurs and it keeps me in the game, but I don’t find it to be as fulfilling and meaningful as doing something massive on my own.

I also wonder if it would not be healthy to make a clean break and take 6 months to a year off just to recharge and clear my mind. It’s unclear to me if in that context I should also stop angel investing to fully disconnect, or maybe only take meetings every other week. Likewise, I have to think through whether it would be a full disconnect to focus on getting really fit playing tennis, kiting and skiing vs. focusing on intellectual pursuits – writing, partaking in intellectual conversations, reading, etc.

I suspect “the right answer” would be a pleasant mix of all the above:

  • Don’t connect at all in two week increments.
  • Mix intellectual and physical pursuits.
  • Spend some time going to see my closest friends wherever they are in the world to spend quality time with them.
  • Make all the angel investing decisions and meetings in 1 or 2 weeks per month.

I would probably not pursue this until my hip is fully healed so that I can make the most of my free time and until the situation regarding the put is resolved one way or another.

What do you think?