Notes on Darryl Rawlings – CEO of Trupanion
July 15, 2022 |
Hugo Thompson


The objectives of this research paper are to give my perspective on Darryl Rawlings and Trupanion, the company he leads. Although I am an undergraduate student – studying for a degree at the University of Manchester, I have insider knowledge of the pet industry: I grew up on a farm in Wales, immersed in a renowned activity holiday and education centre for dogs, called The Dog House Ltd. Also, my mother is the CEO of two high-end dog food businesses, Caboodle Ltd and The Dog House Trading Company Ltd. The reader should not take any of what is written here as conclusive or authoritative. Rather they should serve as a pretext for further conversation. If you have any thoughts or reactions, feel free to send me an email: [email protected]


Darryl Rawlings is the founding CEO of Trupanion.

Key features of Trupanion’s business:

  • Long-term growth company.
  • Market: North American pet insurance – large, underpenetrated market.
  • Economics: Compounding, monthly recurring cash flow.
  • Moats: Difficult to replicate.
  • Financials: 20%+ revenue growth & strong returns on invested capital, not yet profitable.
  • Position: Leading the category.
  • The problem being solved: It is very difficult for pet owners to budget for veterinary expenses if/when their pet becomes sick or injured.
  • How? Trupanion eliminates uncertainty around cost of care: very lucky pets subsidize unlucky pets.

1Darryl Rawlings’ character

Rawlings leads with purpose

  • His integrity seems genuine, conveying honesty and trustworthiness. Although he is a strong salesman, it seems very unlikely that he is culpable to virtue signalling.
  • Extremely driven, long term growth orientated entrepreneur, intelligent, and humble: He built the firm from the ground-up ensuring quality of care through strong relationships with veterinarians and their staff.
  • Fanatical pet lover – Rawlings passionately advocates for responsible pet ownership in several interviews.
  • Rawlings always wanted to start Trupanion because of a traumatic childhood memory of his family having to euthanise his 2yr old dog. This was a result of his parents being unable to budget to afford its treatment.
  • Dan Levitan who is the CEO of Maveron, the largest initial investor in Trupanion, said in an interview with Motley Fool: ‘I met the nine-person Trupanion team at the time. It was a super small company. They had 5,000 pets that they insured at the time. And one of the people I talked to was David Rawlings. I said, “You’ve got the same name as the CEO. What’s your relation?” He said, “I’m Darryl’s dad.” I said, “Oh, that’s interesting. Tell me about Darryl.” And the first word out of Darryl’s dad’s mouth was Darryl has alwayswanted to build a pet insurance company.’ (Motley Fool, 2017).
  • In the last two sentences of Trupanion’s 2017 shareholder letter, Rawlings emphasises: ‘I believe that over the long run, doing things the right way, for the right reasons, will outperform other motivations’ (Trupanion Shareholder Letter, 2017).
  • Rawlings: ‘I never started the company to make money. I started the company to solve the problem. And if you solve a problem, well, it needs to be economically viable for it to be sustainable. If we’re going to be able to impact tens of millions of pets, which we will do, it needs to be economically viable. But it’s not the starting point. Most people that are [involved] in insurance, are thinking about how to make money. And I just think it’s the wrong starting place. I mean, do we want to make money off our children’s health? No. Not where I want to spend my day.’ (Versch, 2022).
  • ‘Maximizing value creation for our shareholders is not our motivation; helping pet owners’ budget and care for their pets is what gets us out of bed’. (Trupanion Shareholder Letter, 2021).
  • Levitan [speaking about Rawlings]: ‘One of the things that Maveron looks for as a private investor [is] great people’. (Motley Fool, 2017).

Negatives on Rawlings

It was difficult to find negative reports about Rawlings’ character apart from especially poor reviews on Comparably, which is an employer ratings site for potential employees.

  • Rawlings’ CEO rating of (D) with an avg. Score of ‘58/100’ from 60 employee ratings.
  • Placed in the bottom 15% of 2022 Similar Sized Companies on ‘Comparably’.
  • Executive team rated at ‘46/100’ by 41 employees (bottom 5% of similar sized companies on ‘Comparably’). TRUP also has a ‘2.8/5’ organisational culture score.

Comparably is a credible source, however, with only 60/1,131 employees leaving reviews the validity of this data is low.

2 People and Culture at Trupanion

The following stood out in the materials that I reviewed:

  • ‘We know that execution – our biggest risk – comes down to people and culture’. (Trupanion Annual Report 2020).
  • ‘There should be no cap on how much any one team member, or team, can receive, with one exception: the CEO. As the CEO, I believe it is important that my compensation does not exceed an internally defined multiple to the median pay of all employees’ (Trupanion Annual Report 2021).
  • ‘Team participation in our equity program is another key priority of ours, aligning us all in our objective to maximise future value creation with limited dilution.’ ‘Our intention is for each team member (full-time or part-time) to receive a new-hire stock grant.’ (Trupanion Shareholder Letter 2015).
  • Rawlings did not read a single CV of approximately the first 300 (and possibly more) employees that worked for the firm. Instead, Rawlings focusses on hiring people that: 1. Have a strong capability to learn at the firm. 2. Are comfortable to fail. 3. Use data to make decisions. (DougCoSchools, 2015).
  • Rawlings: ‘When I was raising capital for Trupanion, I brought a variety of big hitters into a room together. I asked them all to raise their hand if they had a pet. For those without their hands raised, I asked them to leave, because unfortunately, they just won’t get what we do. I require everyone who joins our Board of Directors to own a pet.’ (exaqueo, 2014). ‘Out of 400+ employees at TRUP, 70% are from the animal health world’ (OMD ventures, 2020).
  • Rawlings pioneered bringing dogs to the workplace, however, all team members now operate in a remote work environment. [There are] ‘250 dogs in our office’ (Motley Fool, 2017). Todd Wenning from Intrinsic Investing said: ‘Our two visits to Trupanion headquarters made it clear that employees care about pets. Most of the customer service representatives had their own pets sitting next to them in their cubicles.’Also, a new pilot project from Trupanion offers a step-by-step guide for bringing dogs into the workplace. (Trupanion Inc, 2022). • There are ‘65% of women in leadership positions’ (Trupanion Annual Report, 2021).
  • ‘You hire good people and treat them well. As a result, they treat your customers well and lines at your hot dog stands are long. You now sell the best hot dog around, for considerably less than anyone, all while making a reasonable margin.’ (Trupanion Annual Report, 2021). • Rawlings reflects on the past 5 years and in each year, there is a reference to how he mismanaged people. The process he created to stop himself from being a roadblock to people, to help individuals be more accountable from the shortcomings of a flat organisational structure. (Trupanion Shareholder Letter, 2018). Evidence from annual reports suggest that he recognises and has a willingness to improve on his shortcomings.
  • Artem Fokin from MOI Global (2018): ‘It’s quite clear Trupanion does what it says. I spent a day at the headquarters, meeting everybody on the executive team and analysing company public communications. One culture element is taking great care of employees. Number two, everybody is equally important. Number three, educational empowerment. Number four, owner mentality and aligned incentives. There’s also frugality and getting the right shareholder base. I believe those to be important cultural elements for the company. I came to believe they exist based on what I saw.’
  • ‘I saw that everybody has the same size desk and the same benefits regardless of whether they are hourly or salaried or tenured with Trupanion. I saw every top C level executive’s desk, including the CEOs, and I can tell you they are indeed of the same size.’ (MOI Global, 2018). • Frugality – ‘Trupanion celebrated its IPO on July 18, 2014: “The traditional celebratory dinner was held picnic-style in Central Park while we dined on Shake Shack burgers”.’ (MOI Global, 2018).
  • Rawlings firmly believes that developing people internally is much more powerful than just buying executives. The Trupanion Proxy Statement in 2019 mentioned how 123 people were promoted internally within the company. ‘Spending a lot of time on education and informing new people that come into the company what our core values are, because our values have guided us through every hard spot that the company has had for the last 17 years’. (Trupanion Annual Report, 2021).
  • Strong alignment of shareholders with management, culture, and values: Shareholder Letters are inspirational, engaging, transparent and unusual. Every annual shareholder letter accentuates the importance of the company’s culture to its success. The latter 3 pages of the 2017 Shareholder Letter highlighted the touching impact the firm had on an extremely happy and grateful customer.
  • ‘We strive to find long-term focused shareholders who understand our business on a deeper level. We are confident that these shareholders will be aligned with our values and best positioned to benefit from our strategy.’ (Trupanion Shareholder Letter, 2015).
  • ‘Our goal is to increase the in-person attendance to our annual shareholder meetings in Seattle. We would like these meetings to one day have attendance representing 80%+ of our outstanding shares. We would like to have the meeting become an avenue for a two-way, lengthy conversation where our long-term, well-educated shareholders not only learn additional specifics about the company but also build an understanding of our people and culture.’ (Trupanion Shareholder Letter 2016).

This is not lip service because:

  • Trupanion provides shareholders with an incredible level of access. [Before remote work was implemented,] MOI Global (2018): ‘you could reach out to the company and go and spend a day at its headquarters in Seattle, meeting pretty much every single top-level executive and learning about the business. You can find them, talk to them, and grasp what motivates them’.
  • MOI Global (2018): Rawlings ‘holds one-hour presentations at Berkshire Hathaway’s annual meetings. After Buffett and Munger are done, Trupanion rents a room in a hotel, and anyone interested in the company can come and listen to Darryl. The choice of venue is incredibly thoughtful. Not many public company CEOs go to Berkshire Hathaway meetings to learn something. The CEO of Trupanion does, and wants to educate people who come, tell them what Trupanion is about. Those who invest in Berkshire are typically people with a long-term investment outlook and mindset. The CEO of Trupanion is appealing to the right people, whom he tries to attract as shareholders for the long term.’

3 Darryl Rawling’s vision for Trupanion

Visionary and long-term oriented, focused on building a strong company by moat building.

  • Rawlings does not overly take short term financial metrics into mind.
  • ‘In my opinion, quarterly and annual results are the two worst measurements of time and performance when it comes to building a company’. (Trupanion Shareholder Letter, 2021)
  • Rawlings is focussing on 10/20/30/40 years ahead: ‘We try to be very disciplined in that. If we can’t acquire pets to get a 30-40% internal rate of return, I’m not spending the money. So, we may grow slower and be more profitable. And that would be disappointing. But I’d be willing to do that. The first quarter of COVID, we pulled back our spending dramatically. And people were like, “Wow, look at profit. They’re so much more profitable now.” I was like, “Yeah, we didn’t enrol as many pets.” So as long as we’re getting the rates of return, we’ll continue to do it. If we can’t get the rates of return, then we can do dividends or do whatever else we want.’ (Trupanion Annual Report, 2021).
  • ‘With Margi Tooth leading the execution of our 60-month plan, I am spending my efforts and energy on the long-term as well as keeping my pulse on our culture and monitoring our daily and monthly progress.’ (Trupanion Shareholder Letter, 2021).

Gradually stepping back from CEO role

  • Plans to step down as CEO in 2025, becoming a supervisory chairman. In 2035, in longterm planning, Rawlings plans to step down as supervisory chairman.
  • Rawlings: ‘I think it’s important that the values that we have and the culture and some of the things remain instilled. I’ve got a very deliberate plan to make sure that this happens. The team takes things and runs with them over a [lengthy] period of time. So, I just think it is the healthiest and the best thing. To be able to attract the best talent, you have to give room. And I’ve been reminded recently, when people stay in power too long, what happens to them. We were all watching it, and it’s not healthy. I think it’s just the right thing to do.’ (Good Investing, 2022).
  • Rawlings is not overly controlling of Trupanion – he wants the company to flourish without his heavy involvement. Rawlings attended very few executive meetings in a successful 2021. (Trupanion Annual Report 2021)
  • Instead, his priority is to make sure core values are kept intact.

4 Factors affecting Trupanion’s success


  • Execution through the success of top management. (Market, product and culture are all there.) ‘Our organisation will look very different at the end of 2025. We will be a lot bigger, and we will need to develop more leaders to keep us moving forward. Doing this well will be the single biggest driver of our success’. (Trupanion Shareholder Letter, 2020).
  • Trupanion will require a visionary leader in the CEO role to replace Rawlings
  • ‘Margi Tooth, president of Trupanion, is leading the execution of a 60-month plan’ (from Jan 2021-December 2025). Tooth is an animal lover who grew up on a farm, and always wanted to become a veterinarian. Tooth joined Trupanion in 2013 as vice president of digital marketing and has since risen through the organisational hierarchy.
  • Success in entering new international markets (EU, UK, Australia, Japan, Brazil) under the management of Simon Wheeler – executive vice president of international business. ‘Wheeler worked with Trupanion’s President, Margi Tooth, while they were both at Allianz in the UK. While partnering together, they realised notable success with Petplan and associated brands, driving pet insurance to become a recognized concept and “the norm” for pet owners.’ (Trupanion Inc, 2021).
  • Ian Moffat (vice president of operations) – has extensive, successful industry experience working with Tooth and Wheeler when working for Petplan and then Allianz.
  • Drew Wolff (CFO), 20 years of strategic and financial management experience. Most recently served as CFO of International for Starbucks. (Trupanion Inc, 2021).
  • Success in penetrating unpenetrated markets. There is a ‘total addressable market of $38.3B in the US and Canada’ (Trupanion Investor Presentation, April 2022).
  • Effectiveness of increasing awareness for pet insurance, especially in global, underpenetrated markets. This can take the form of creating further synergies and affiliations with veterinaries and brands in the pet market.
  • Effective capital allocation. For example, shareholders were dismayed by the decision to acquire a building for $65 million USD on 20th June 2018. (MOI Global, 2018).


  • Regulatory matters will likely put speed bumps in Trupanion’s growth (Rawlings anticipates this and promises to work more closely with regulators).
  • Competitor growth. More and more insurance players have entered the pet insurance market (Lemonade, AXIS, Metlife), which could adversely affect the average price per pet. This has contributed to a significant increase in Trupanion’s acquisition costs. The North American pet insurance market is still massively underpenetrated and is in its very early stages (2% of pet owners in USA have pet insurance, in the UK it is 25%). Therefore, it is likely that larger corporations are likely to enter the space as the pet insurance market expands.

5 Trupanion’s competitive advantages and barriers to entry

  • Trupanion currently has a superior customer value proposition in the market.
  • The company has built long-standing, close relationships and integration with veterinarians. It is unlikely that competitors would be able to persuade veterinarians to learn how to operate new software after they’ve been dealing with Trupanion Express for 10+ years.
  • 24/7 customer service.
  • ‘Only brand with software enabling direct payment to veterinarian at time of checkout’ (Trupanion Investor Presentation, April 2022).
  • The broadest coverage in the market: comprehensive lifelong coverage for pet illness or injury. Freedom to choose any veterinarian. Covers hereditary and congenital conditions.
  • Understanding data. Trupanion has over 20 years of pet data in their system which enables extremely precise and accurate price setting for customers. (OMD ventures, 2020).
  • Strong, mission driven culture from heavy investment in people and culture.
  • Vertically integrated: Trupanion underwrites its own policies, owns the data, owns the brand, owns their office building, and is the managing general agent of the entire operation. Therefore, Trupanion benefits from greater efficiencies and cheaper supplies which can undercut new entrants/competitors.
  • Homogenous, specialised firm that is likely to compete better than multifaceted firms such as Nationwide and Aviva.
  • Trupanion appears to be the only U.S pet insurer with a nationwide salesforce. Based on LinkedIn, Trupanion has over 100 territory partners while Nationwide appears to have around thirty, Pethealth has around twenty, and the rest have less than ten. Strong partnerships. E.g in December 2021, Trupanion and Chewy partnered to offer exclusive health insurance plans to more than 20 million Chewy customers. (GM insights, 2022).
  • Economies of scale – ‘Total enrolled pets was 1,267,253 on March 31, 2022, an increase of 34% over the first quarter of 2021.’ (Trupanion First Quarter Annual Results, 2022).
  • Product differentiation – Trupanion has a strong brand image and a very high and consistent customer retention rate, (98.7% average monthly retention rate since 2010). Therefore, it would require high start-up costs, high sunk costs, and a long growth time to acquire Trupanion’s customers and veterinarians, due to the firm possessing extremely high brand loyalty. Thus, the level of competition is reduced because firms are discouraged from entering the market.

6 Trupanion’s competitive weaknesses

  • Pricing – Trupanion could possibly be undercut by competitors charging lower prices and allowing for greater insurance policy choice/flexibility. ‘Trupanion’s policies cost about $600 to $1,500 annually and don’t cover wellness visits, estimates are, in the case of dogs, (85% of the pet market), a more realistic target customer would be owners who earn $85,000 or more a year.’ (Barron’s, 2018). Competitors such as Healthy Paws are more affordable and offer greater flexibility. Their policies start at a lower price point due to a wider range of customization options. Since Trupanion’s policies can only be adjusted by changing the deductible, premiums tend to be higher. The estimated cost of an accident and illness policy with no annual limit, 90% reimbursement, and a $250 annual deductible was $35.66 per month for Healthy Paws. Whereas Trupanion was over 50% more expensive at $54.60 per month.’ (Investopedia, 2022).
  • Insiders exiting. In the last 8 years, insiders at Trupanion have sold an estimated value of $124.4M and bought an estimated value of $10.29M worth of shares. Rawlings has gradually sold much of his stock holding in Trupanion. From 7.2% (July 27, 2018) to 3.50% (6 July 2022). [(MOI Global, 2018), (Bloomberg L.P, 2022)]. Dan Levitan (partner of Trupanion and co-founder of Maveron, the largest initial investor in Trupanion, had a 25% share in 2014 and has recently sold all his shares in the firm.
  • Online reviews and reputation. A competitor, Healthy Paws is extremely well rated, receiving top marks from most third-party reviewers. Its policy underwriter, Chubb, gets an A++ rating for financial stability from AM best. In contrast, Trupanion’s reviews are ‘less than glowing’. (Investopedia, 2022). During the annual meeting Q&A Rawlings claimed that many of these review websites are pay-to-play and that Trupanion has historically not paid as much as their competitors for better rankings.
  • Rising pet acquisition costs.
  • Most insurers make money by investing the “float” from premiums, but Trupanion does not. Therefore, they are potentially losing out on a large amount of extra capital.
  • Lack of profitability. Will Trupanion’s profit ever correspond to its market valuation?

7 Does Trupanion fit Warren Buffett’s investing principles?


  • It is an extremely large business with wide economic moats.
  • TRUP possesses a highly predictable, stable, and recurring base of revenue. – In 2021, the company made $699 million in total revenue across 1.1 million+ pets, with its top line increasing 39% year over year and its total enrolled pets growing by 36% in comparison to 2020. That caps off an uninterrupted five-year growth streak over which the company’s annual revenue increased by 188%. (Trupanion Annual Report, 2021).
  • Massively underpenetrated market with a focus for multi-decades of long-term growth – penetration of medical pet insurance in North America is extraordinarily low, currently between 1.5% and 2%, compared to the UK at 25%. Rationale: The North American market is simply lagging the European market.
  • Trupanion’s favourable unit economics means that the firm doesn’t necessarily need to raise additional capital to grow.
  • Strong financial health in the form of minimal debt load. TRUP is only $800,000 in debt. (Trupanion Annual Report, 2021).
  • The firm has relatively low variable costs. Variable expenses associated with providing insurance only accounts for 9.8% of subscription revenue.
  • Trupanion is over-performing intrinsic value growth expectations.
  • The company has developed a strong alignment of shareholders with company values.


  • Indefensible market share. TRUP claims it has strong moats in the form of Trupanion express and relationships with veterinarians. However, is this enough to attract customers from lower-priced alternatives in the future?
  • No profitability trends attained. Although, this is due to heavy reinvestment in growth.
  • Insiders selling. In the last 8 years, insiders at Trupanion have sold an estimated value of $124.4M and bought an estimated value of $10.29M worth of shares. (Benzinga, 2022). Is this a sign that the stock price is overvalued?
  • High and rising customer acquisition costs ($287 in 2021) compared to ($247 in 2020). (Trupanion Annual Report 2021).

8 Forces of change that are increasing demand for pet insurance in Trupanion’s target markets.

Pet insurance premiums written in the USA amounted to $2 billion USD in 2020, up from $500 million USD in 2013 (NAPHIA, 2021). Also, the U.S Pet Insurance market size grew at 23% industry revenue CAGR between 2015 and 2020 (NAPHIA, 2021).

  • Increasing discretionary income = increasing pet ownership and increasing propensity to provide better care for pets.
  • Increasingly atomised societies, increase in remote work = shift of consumers’ humanhuman relationships to human-pet relationships = increasing pet ownership and increasing propensity to expend greater capital on pets. Share of households owning a pet in the United Kingdom (UK) has increased from 41% (2019-2020) – 62% (2021-2022). (PFMA, 2022). – Mostly attributed to Covid-19 and increased time spent at home.
  • Increasing public awareness that pet adoption aids depression, loneliness, low blood pressure etc. = Increasing pet ownership. • Reduction in birth rate and childbirth happening at older ages in target countries = Increasing pet ownership.
  • Increasing awareness about pet insurance policies (especially in North America where current uptake is very poor.)
  • Improved innovative pet insurance coverage offerings.
  • Disproportionately rising veterinary service costs (GM insights, 2022).

List of Resources

Barron’s, 2018. Shares of Pet Insurer Trupanion Are Overvalued.
Available at:

Benzinga, 2022. Margaret Tooth Net Worth & Insider Trades.
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Bloomberg L.P. Terminal. Bloomberg 2022.
Comparably, 2022. Darryl Rawlings Trupanion CEO rating.
Available at:

DougCoSchools, 2015. Create Something Great – Darryl Rawlings.
Available at:

Exaqueo, 2014. Startup Culture: Q&A with Trupanion’s Darryl Rawlings.
Available at:

GM insights, 2022. Pet Insurance Market.
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Intrinsic Investing, 2019. Intrinsic Investing.
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Investopedia., 2022. Trupanion vs. Healthy Paws.
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Investors Chronicle., 2017. Supersize Returns V.
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MOI Global, 2018. Trupanion: Moat Based on Proprietary Data and Virtuous Cycle Flywheels.
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Motley Fool, 2017. The Motley Fool Interviews Trupanion Founder and CEO Darryl Rawlings.
Available at:

NAPHIA, 2021. State of the Industry Report. North America Gross Written Premiums in USD,
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NAPHIA, 2021. Total premium volume for pet insurance in the United States from 2013 to 2020 (in million U.S. dollars).
Available at:

OMD ventures, 2020. Trupanion (TRUP).
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PFMA, 2022. Share of households owning a pet in the United Kingdom (UK) from 2011/12 to 2021/22.
Available at:

Trupanion Inc, 2015. 2015 Shareholder Letter.

Trupanion Inc, 2016. 2016 Shareholder Letter.

Trupanion Inc, 2017. 2017 Shareholder Letter.

Trupanion Inc, 2018. 2018 Shareholder Letter.

Trupanion Inc, 2019. 2019 Proxy Statement.

Trupanion Inc, 2020. 2020 Annual Report.

Trupanion Inc, 2020. 2020 Shareholder Letter.

Trupanion Inc, 2021. 2021 Annual Report.

Trupanion Inc, 2021. 2021 Shareholder Letter.

Trupanion Inc, 2021. Trupanion Eyes International Growth and Expansion – Names Simon Wheeler as EVP of International Business.
Available at:

Trupanion Inc, 2021. Trupanion Promotes Drew Wolff to Chief Financial Officer.
Available at:

Trupanion Inc, 2022. Trupanion Reports First Quarter 2022 Results. 22 April.
Trupanion Inc, 2022. April 2022 Trupanion Investor Presentation.
Available at:

Trupanion Inc, 2022. “Working K9 to 5” Helps Employers Create Dog-Friendly Offices.
Available at:

Versch, T., 2022. Darryl Rawlings, what is Trupanion doing to win the pet insurance market?
Available at:

You can access the White Paper here.


I’m a Zurich based investor. Since 1997, I’ve managed a privately offered investment fund known as the Aquamarine Fund.

I am also the author of a book titled The Education of a Value Investor, which was published in 2014.

As I wrote in my book, we are all a work in progress. This site documents my ongoing quest for “wealth, wisdom and enlightenment”.

I have created a /now page – inspired by Derek Sivers

I’m a Zurich based investor. Since 1997, I’ve managed a privately offered investment fund known as the Aquamarine Fund.

I am also the author of a book titled The Education of a Value Investor, which was published in 2014.

As I wrote in my book, we are all a work in progress. This site documents my ongoing quest for “wealth, wisdom and enlightenment”.

I have created a /now page – inspired by Derek Sivers

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