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Darryl Rawlings net worth and biography

Darryl Rawlings Biography and Net Worth

CEO of Trupanion

Darryl Rawlings is the founder and CEO of Trupanion, a leading medical insurance provider for pets. 

As a pet lover, Rawlings appreciated the special relationship that is formed between pets, owners and veterinarians. That appreciation led him to invent a new version of pet insurance that benefited all parties involved. Under Rawlings’ leadership, Trupanion has grown to serve over 650,000 pets and a team of more than 1,000.

Spurred by the memory of losing a cherished family dog to a treatable but expensive illness, Rawlings looked to flip the standard pet insurance reimbursement model to a direct payment approach. By paying veterinarians at the time of the invoice, Trupanion alleviates the out-of-pocket costs pet owners feel when an unexpected procedure comes up while simultaneously guaranteeing payment to the vet. 

Rawlings is the mastermind behind this win-win approach by being the first pet insurance company to develop a network of territory partners who work with local veterinarians to create long-term success. 

Rawlings guided Trupanion through its IPO in 2014 which netted the company $75 million. When he founded the company in 2000, Rawlings’ dog Monty was the first pet to be enrolled with Trupanion insurance. 

By 2004, the company was the first North American pet insurance provider to become profitable and boasted the highest retention rate and consumer satisfaction marks in the industry. Rawlings expanded Trupanion to the U.S. market in 2005 where it became the first North American pet insurance company licensed to manage its own underwriting.

The pet insurance executive founded his first business in 1994—the Canadian Cigar Company. Rawlings oversaw the importation of over 1,000 kinds of cigars from around the world as the company served clubs, hotels, golf resorts, retail stores, and bars. He sold the company in 1999, rolling the funds into the launch of Trupanion that same year. 

Before his career as an entrepreneur, Rawlings was the director of sales and marketing at cellular network company, Telos Engineering. He also sold encryption technology at Cycomm International. 

Rawlings holds a degree from the British Columbia Institute of Technology. 

What is Darryl Rawlings' net worth?

The estimated net worth of Darryl Rawlings is at least $19.09 million as of May 8th, 2023. Mr. Rawlings owns 829,109 shares of Trupanion stock worth more than $19,086,089 as of June 2nd. This net worth estimate does not reflect any other assets that Mr. Rawlings may own. Learn More about Darryl Rawlings' net worth.

What is Darryl Rawlings' salary?

As the CEO of Trupanion, Inc., Mr. Rawlings earned a total compensation package of $4,962,422.00 in 2021. Mr. Rawlings earned a salary of $300,000.00, stock awards of $4,623,067.00, non-equity compensation of $39,355.00, and no other miscellaneous compensation. Learn More on Darryl Rawlings' salary.

How do I contact Darryl Rawlings?

The corporate mailing address for Mr. Rawlings and other Trupanion executives is 6100 4TH AVENUE SOUTH SUITE 200, SEATTLE WA, 98108. Trupanion can also be reached via phone at (855) 727-9079 and via email at [email protected]. Learn More on Darryl Rawlings' contact information.

Has Darryl Rawlings been buying or selling shares of Trupanion?

During the last quarter, Darryl Rawlings has sold $407,920.00 of Trupanion stock. Most recently, Darryl Rawlings sold 4,000 shares of the business's stock in a transaction on Monday, May 8th. The shares were sold at an average price of $25.30, for a transaction totalling $101,200.00. Following the completion of the sale, the chief executive officer now directly owns 829,109 shares of the company's stock, valued at $20,976,457.70. Learn More on Darryl Rawlings' trading history.

Who are Trupanion's active insiders?

Trupanion's insider roster includes Asher Bearman (Insider), Michael Doak (Director), Robin Ferracone (Director), Gavin Friedman (EVP), Dan Levitan (Director), Murray Low (Director), Tricia Plouf (CFO), Darryl Rawlings (CEO), Howard Rubin (Director), and Margaret Tooth (Insider). Learn More on Trupanion's active insiders.

Are insiders buying or selling shares of Trupanion?

During the last year, insiders at the financial services provider sold shares 32 times. They sold a total of 101,757 shares worth more than $5,695,849.14. The most recent insider tranaction occured on May, 8th when CEO Darryl Rawlings sold 4,000 shares worth more than $101,200.00. Insiders at Trupanion own 5.9% of the company. Learn More about insider trades at Trupanion.

Information on this page was last updated on 5/8/2023.

Darryl Rawlings Insider Trading History at Trupanion

Transaction DateBuy/SellNumber of SharesAverage Share PriceTotal TransactionShares Held After TransactionDetails
5/8/2023Sell4,000$25.30$101,200.00829,109View SEC Filing Icon  
4/19/2023Sell4,000$35.48$141,920.00833,109View SEC Filing Icon  
4/4/2023Sell4,000$41.20$164,800.00837,109View SEC Filing Icon  
3/16/2023Sell4,000$55.17$220,680.00841,109View SEC Filing Icon  
2/28/2023Sell4,000$58.10$232,400.00845,109View SEC Filing Icon  
2/13/2023Sell4,000$58.50$234,000.00849,109View SEC Filing Icon  
1/26/2023Sell4,000$54.33$217,320.00853,109View SEC Filing Icon  
1/9/2023Sell4,000$48.54$194,160.00857,109View SEC Filing Icon  
12/23/2022Sell4,000$48.96$195,840.00861,109View SEC Filing Icon  
12/7/2022Sell4,000$51.03$204,120.00861,109View SEC Filing Icon  
11/18/2022Sell4,000$60.41$241,640.00865,109View SEC Filing Icon  
11/3/2022Sell4,000$44.16$176,640.00857,109View SEC Filing Icon  
10/17/2022Sell4,000$53.94$215,760.00857,109View SEC Filing Icon  
9/30/2022Sell4,000$61.38$245,520.00857,109View SEC Filing Icon  
9/14/2022Sell4,000$65.57$262,280.00857,109View SEC Filing Icon  
8/8/2022Sell4,000$66.86$267,440.00865,109View SEC Filing Icon  
7/26/2022Sell4,000$64.21$256,840.00857,109View SEC Filing Icon  
7/7/2022Sell4,000$66.11$264,440.00861,109View SEC Filing Icon  
6/21/2022Sell4,000$53.10$212,400.00865,109View SEC Filing Icon  
6/2/2022Sell4,000$66.52$266,080.00869,109View SEC Filing Icon  
5/17/2022Sell4,000$64.90$259,600.00857,109View SEC Filing Icon  
4/29/2022Sell4,000$70.37$281,480.00857,109View SEC Filing Icon  
4/13/2022Sell4,000$84.86$339,440.00853,109View SEC Filing Icon  
3/28/2022Sell4,000$90.80$363,200.00View SEC Filing Icon  
3/11/2022Sell4,000$81.04$324,160.00View SEC Filing Icon  
2/22/2022Sell4,000$79.22$316,880.00View SEC Filing Icon  
2/4/2022Sell4,000$90.51$362,040.00View SEC Filing Icon  
1/19/2022Sell4,000$97.29$389,160.00View SEC Filing Icon  
12/15/2021Sell4,000$120.48$481,920.00View SEC Filing Icon  
11/29/2021Sell4,000$123.85$495,400.00View SEC Filing Icon  
11/11/2021Sell4,000$123.57$494,280.00View SEC Filing Icon  
10/25/2021Sell4,000$109.60$438,400.00View SEC Filing Icon  
10/7/2021Sell4,000$83.78$335,120.00View SEC Filing Icon  
9/22/2021Sell4,000$83.97$335,880.00View SEC Filing Icon  
9/7/2021Sell4,000$86.56$346,240.00View SEC Filing Icon  
8/19/2021Sell4,000$86.36$345,440.00View SEC Filing Icon  
8/3/2021Sell4,000$113.83$455,320.00View SEC Filing Icon  
7/16/2021Sell4,000$105.07$420,280.00View SEC Filing Icon  
6/14/2021Sell4,000$98.23$392,920.00View SEC Filing Icon  
5/26/2021Sell4,000$85.08$340,320.00544,162View SEC Filing Icon  
5/7/2021Sell4,000$79.71$318,840.00View SEC Filing Icon  
4/21/2021Sell4,000$79.70$318,800.00585,943View SEC Filing Icon  
4/6/2021Sell4,000$75.65$302,600.00View SEC Filing Icon  
3/17/2021Sell4,000$91.92$367,680.00View SEC Filing Icon  
2/24/2021Sell97,118$100.66$9,775,897.88453,146View SEC Filing Icon  
2/12/2021Sell4,000$106.81$427,240.00382,585View SEC Filing Icon  
1/26/2021Sell4,000$120.27$481,080.00View SEC Filing Icon  
1/8/2021Sell4,000$121.16$484,640.00View SEC Filing Icon  
12/23/2020Sell4,000$124.52$498,080.00View SEC Filing Icon  
12/7/2020Sell4,000$99.52$398,080.00View SEC Filing Icon  
11/18/2020Sell4,000$94.64$378,560.00View SEC Filing Icon  
11/2/2020Sell4,000$72.98$291,920.00View SEC Filing Icon  
10/15/2020Sell4,000$92.49$369,960.00View SEC Filing Icon  
9/29/2020Sell4,000$73.95$295,800.00View SEC Filing Icon  
9/14/2020Sell4,000$71.50$286,000.00View SEC Filing Icon  
8/11/2020Sell4,000$63.97$255,880.00View SEC Filing Icon  
7/23/2020Sell4,000$50.91$203,640.00View SEC Filing Icon  
7/8/2020Sell4,000$45.18$180,720.00View SEC Filing Icon  
6/22/2020Sell4,000$39.51$158,040.00View SEC Filing Icon  
6/3/2020Sell4,000$33.21$132,840.00View SEC Filing Icon  
5/1/2020Sell4,000$28.84$115,360.00View SEC Filing Icon  
4/14/2020Sell4,000$29.96$119,840.00View SEC Filing Icon  
3/30/2020Sell4,000$25.84$103,360.00View SEC Filing Icon  
3/12/2020Sell4,000$25.51$102,040.00View SEC Filing Icon  
2/25/2020Sell4,000$31.12$124,480.00454,237View SEC Filing Icon  
2/7/2020Sell4,000$33.22$132,880.00View SEC Filing Icon  
1/22/2020Sell4,000$32.83$131,320.00View SEC Filing Icon  
1/6/2020Sell4,000$36.10$144,400.00View SEC Filing Icon  
12/19/2019Sell4,000$35.52$142,080.00468,277View SEC Filing Icon  
11/13/2019Sell4,000$31.26$125,040.001,446,499View SEC Filing Icon  
10/25/2019Sell4,000$22.45$89,800.001,450,499View SEC Filing Icon  
10/10/2019Sell4,000$21.43$85,720.001,454,499View SEC Filing Icon  
9/24/2019Sell4,000$26.81$107,240.001,458,499View SEC Filing Icon  
9/6/2019Sell4,000$23.92$95,680.001,462,499View SEC Filing Icon  
8/21/2019Sell4,000$24.62$98,480.001,465,759View SEC Filing Icon  
8/5/2019Sell4,000$30.18$120,720.001,473,759View SEC Filing Icon  
7/18/2019Sell4,000$32.59$130,360.001,515,120View SEC Filing Icon  
7/2/2019Sell4,000$35.42$141,680.001,519,120View SEC Filing Icon  
6/20/2019Sell4,000$36.48$145,920.001,523,120View SEC Filing Icon  
6/4/2019Sell4,000$29.95$119,800.001,527,120View SEC Filing Icon  
5/20/2019Sell4,000$31.17$124,680.001,530,380View SEC Filing Icon  
5/2/2019Sell4,000$33.19$132,760.001,534,380View SEC Filing Icon  
4/16/2019Sell4,000$35.04$140,160.001,538,380View SEC Filing Icon  
3/28/2019Sell4,000$30.95$123,800.001,542,380View SEC Filing Icon  
3/12/2019Sell4,000$30.10$120,400.001,546,380View SEC Filing Icon  
2/25/2019Sell4,000$29.70$118,800.001,547,421View SEC Filing Icon  
2/6/2019Sell4,000$28.45$113,800.001,551,421View SEC Filing Icon  
1/22/2019Sell4,000$27.14$108,560.001,555,421View SEC Filing Icon  
1/2/2019Sell4,000$25.97$103,880.001,559,421View SEC Filing Icon  
12/18/2018Sell4,000$23.94$95,760.001,563,421View SEC Filing Icon  
12/4/2018Sell4,000$28.49$113,960.001,567,421View SEC Filing Icon  
11/19/2018Sell81,053$25.78$2,089,546.341,652,474View SEC Filing Icon  
11/15/2018Sell85,053$23.61$2,008,101.331,555,997View SEC Filing Icon  
11/12/2018Sell81,054$25.47$2,064,445.381,455,520View SEC Filing Icon  
10/31/2018Sell4,000$25.81$103,240.001,273,989View SEC Filing Icon  
10/12/2018Sell4,000$29.04$116,160.001,277,989View SEC Filing Icon  
9/26/2018Sell4,000$36.81$147,240.001,281,989View SEC Filing Icon  
9/11/2018Sell4,000$34.74$138,960.001,285,989View SEC Filing Icon  
8/24/2018Sell4,000$37.21$148,840.001,289,989View SEC Filing Icon  
8/8/2018Sell4,000$38.18$152,720.001,293,989View SEC Filing Icon  
7/23/2018Sell4,000$45.72$182,880.00View SEC Filing Icon  
7/5/2018Sell4,000$38.18$152,720.00View SEC Filing Icon  
6/15/2018Sell4,000$39.17$156,680.001,351,976View SEC Filing Icon  
5/30/2018Sell4,000$32.76$131,040.001,355,976View SEC Filing Icon  
5/15/2018Sell4,000$27.53$110,120.001,359,976View SEC Filing Icon  
4/27/2018Sell4,000$26.05$104,200.001,363,976View SEC Filing Icon  
4/10/2018Sell4,000$26.72$106,880.001,367,976View SEC Filing Icon  
3/26/2018Sell4,000$29.71$118,840.001,371,976View SEC Filing Icon  
3/8/2018Sell3,500$31.93$111,755.001,375,976View SEC Filing Icon  
2/20/2018Sell3,500$28.42$99,470.001,379,476View SEC Filing Icon  
2/1/2018Sell3,500$34.36$120,260.001,382,976View SEC Filing Icon  
1/16/2018Sell3,500$34.08$119,280.001,386,476View SEC Filing Icon  
12/27/2017Sell3,500$30.11$105,385.001,389,976View SEC Filing Icon  
12/13/2017Sell3,500$30.10$105,350.001,393,476View SEC Filing Icon  
9/20/2017Sell3,500$23.75$83,125.001,446,005View SEC Filing Icon  
9/6/2017Sell3,500$21.13$73,955.001,449,505View SEC Filing Icon  
8/24/2017Sell3,500$22.30$78,050.001,453,005View SEC Filing Icon  
8/8/2017Sell3,500$22.81$79,835.001,456,505View SEC Filing Icon  
7/20/2017Sell3,500$22.51$78,785.001,460,005View SEC Filing Icon  
7/5/2017Sell3,500$22.20$77,700.001,463,505View SEC Filing Icon  
6/22/2017Sell3,500$21.28$74,480.001,467,005View SEC Filing Icon  
6/6/2017Sell3,500$21.16$74,060.001,470,505View SEC Filing Icon  
5/18/2017Sell3,500$16.90$59,150.001,474,005View SEC Filing Icon  
4/20/2017Sell3,500$14.86$52,010.001,481,005View SEC Filing Icon  
4/4/2017Sell3,500$14.44$50,540.001,484,505View SEC Filing Icon  
3/23/2017Sell3,500$14.46$50,610.001,488,005View SEC Filing Icon  
2/23/2017Sell3,500$16.07$56,245.001,495,005View SEC Filing Icon  
2/7/2017Sell3,500$16.43$57,505.001,498,505View SEC Filing Icon  
1/19/2017Sell3,500$14.00$49,000.001,502,005View SEC Filing Icon  
1/3/2017Sell3,500$15.55$54,425.001,505,505View SEC Filing Icon  
12/22/2016Sell3,500$15.73$55,055.001,509,005View SEC Filing Icon  
11/2/2016Sell3,500$14.95$52,325.001,519,505View SEC Filing Icon  
10/20/2016Sell3,500$16.15$56,525.001,523,005View SEC Filing Icon  
10/4/2016Sell3,500$16.21$56,735.001,526,505View SEC Filing Icon  
6/17/2016Sell4,000$12.72$50,880.001,572,095View SEC Filing Icon  
6/2/2016Sell4,000$13.85$55,400.001,576,095View SEC Filing Icon  
5/18/2016Sell3,500$15.04$52,640.001,580,095View SEC Filing Icon  
5/3/2016Sell3,500$12.64$44,240.001,583,595View SEC Filing Icon  
4/20/2016Sell3,500$12.15$42,525.001,587,095View SEC Filing Icon  
4/5/2016Sell3,500$9.56$33,460.001,590,595View SEC Filing Icon  
3/23/2016Sell3,500$9.40$32,900.001,594,095View SEC Filing Icon  
2/17/2016Sell3,500$9.75$34,125.001,601,095View SEC Filing Icon  
2/2/2016Sell3,500$8.24$28,840.001,604,595View SEC Filing Icon  
1/20/2016Sell3,500$7.92$27,720.001,608,095View SEC Filing Icon  
1/5/2016Sell3,500$9.28$32,480.001,611,595View SEC Filing Icon  
12/22/2015Sell3,500$9.11$31,885.001,615,095View SEC Filing Icon  
12/8/2015Sell3,500$8.69$30,415.001,618,595View SEC Filing Icon  
11/18/2015Sell3,500$7.51$26,285.001,622,095View SEC Filing Icon  
11/2/2015Sell3,500$6.70$23,450.001,625,595View SEC Filing Icon  
10/21/2015Sell3,500$7.00$24,500.001,629,095View SEC Filing Icon  
10/6/2015Sell3,500$7.40$25,900.001,632,595View SEC Filing Icon  
9/24/2015Sell3,500$8.17$28,595.001,636,095View SEC Filing Icon  
9/8/2015Sell3,500$7.33$25,655.001,639,595View SEC Filing Icon  
8/19/2015Sell3,500$7.81$27,335.001,643,095View SEC Filing Icon  
7/22/2015Sell3,500$8.46$29,610.00View SEC Filing Icon  
7/7/2015Sell3,500$7.99$27,965.00View SEC Filing Icon  
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Darryl Rawlings Buying and Selling Activity at Trupanion

This chart shows Darryl Rawlings's buying and selling at Trupanion by year and by quarter.

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Trupanion Company Overview

Trupanion logo
Trupanion, Inc. engages in the provision of medical insurance for cats and dogs. It operates through the Subscription Business and Other Business. The Subscription Business segment is involved in the monthly subscriptions of pet medical insurance. The Others Business segment includes companies or organizations that choose to provide medical insurance for cats and dogs as a benefit to their employees or members. The company was founded by Darryl Rawlings in 2000 and is headquartered in Seattle, WA.
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Today's Range

Now: $23.02
Low: $21.50
High: $23.28

50 Day Range

MA: $31.35
Low: $20.13
High: $44.12

2 Week Range

Now: $23.02
Low: $19.64
High: $82.49


1,014,315 shs

Average Volume

1,797,924 shs

Market Capitalization

$948.88 million

P/E Ratio


Dividend Yield



The Ultimate Passive Income Play
The #1 income play for 2023 is NOT a stock, bond or private company... Rather, it's a little-known alternative investment that could hand you big monthly income from oil and gas. 

Find Out What It Is Right Here.