Jimmy Flannigan has a long history of avoiding financial responsibility and he isn’t the small business owner he claims in campaign material
Jimmy Flannigan serves on the City Council’s Audit and Finance Committee. He votes on Austin’s $4.2 billion budget. But he has struggled to manage his own finances, both personally and in his business dealings.
The Austin Bulldog’s investigation reveals Flannigan was sued repeatedly by lenders for unpaid debts, both in Williamson County and in Travis County.
Lenders won default judgments in two Williamson County cases. Flannigan contested a suit in Travis County but lost at trial.
Lenders placed liens against a home Flannigan owns in Williamson County, and he narrowly avoided losing it.
Two liens against this home weren’t lifted until November 2019 and December 2019—nearly three years into his term of office—and then only because another lender who hoped to buy the home settled a portion of the outstanding debt.
Flannigan’s personal finances appear to have since improved, thanks in large part to his council member’s annual pay of $79,934. But some of his debts were settled at a discount—meaning the lenders never got all of their money back. He also remains indebted, his business no longer exists, and he doesn’t pay his own mortgage, according to the Bulldog’s investigation.
Though these revelations pertain to Flannigan’s personal finances, the Bulldog is revealing them because Flannigan, as a sitting city council member, is entrusted with substantial powers over public finances.
Through a staff member, Flannigan initially scheduled an interview with the Bulldog to discuss the revelations in this story, but later canceled and instead emailed written responses to some but not all of the Bulldog’s questions.
In his written response he characterized his struggles with money as long past, and not a reflection on his ability to make big decisions about the city’s finances: “Like many small business owners, I’ve learned from past experiences and have used those lessons to create future success.”
“My record on the council has been one of staunch fiscal responsibility, as evidenced by the fact that I’ve voted against two of the last four city budgets,” he said, also pointing to votes against “questionable procurements and contracts.”
The Austin Bulldog verified his claim about voting on the budget. Final budget adoption in 2019 was 10-1 with Flannigan against; in 2017 it was 10-3.
Flannigan, 42, is running for reelection and has three opponents: Dee Harrison, 66; Mackenzie Kelly, 34, who like Flannigan ran unsuccessfully for the District 6 seat in 2014; and Jennifer Mushtaler, 49.
Early business hopes
Before seeking public office, Jimmy Flannigan started and ran an Internet business in the late 1990s during his years at the University of Texas at Austin. That’s where while in his early twenties he learned to make websites in his dorm room.
A bad business experience early on spurred him to invest in a home from which he could work—before even graduating college. “One of the first organizations I worked with had their website hosted on a server in my dorm room; a dorm room that I had to leave over the summer,” Flannigan said in a 2012 interview.
“That left their website offline from June to August. It was definitely something that would never be acceptable now,” he recalled in the interview, which was published by BusinessInterviews.com, a public relations website.
“I tried reselling hosting services for a couple months but after one hosting outage I was left feeling helpless and having to answer calls from angry clients. I decided then that if I was going to have to deal with the repercussions of downtime, I should at least have the control over its resolution.”
For Flannigan, “control over its resolution” meant having a home of his own where he could keep his servers. In July 2000, after his third year in college, he took out a $102,900 mortgage to pay for a home at 12505 Shasta Lane. The initial interest rate was 8.125 percent, roughly the average mortgage rate at the time.
Loan documents listed an Austin street address, though maps today show the home to be in an unincorporated part of Williamson County and just a block outside the boundaries of what is now his council District 6.
“Wilco was where I could afford in 2000,” Flannigan told the Bulldog in an email. “My parents co-signed the loan.”
He graduated from the University of Texas at Austin in May 2001 with a Bachelor of Business Administration, with a major in management information systems. He dedicated himself to his business, Site Street, which offered a variety of web services. Secretary of State records show that he incorporated Site Street Inc. December 23, 2002, naming himself as the sole director.
Flannigan had picked a promising but competitive industry. Web technologies would evolve rapidly in coming years, making it a field in which skills constantly had to be updated. And Flannigan’s business suffered from several disadvantages early on.
In the first place, he initially split his time between working and studying, enrolling for a Master’s in e-Business from the University of Phoenix, a for-profit school. He completed the online-only degree in 2003, according to his LinkedIn profile.
That commitment saddled Flannigan with student loans while also cutting into the hours that he was able to devote to growing his business and honing his on-the-job skills.
Secondly, though Flannigan had technical training, he was weaker on the aesthetic side of website design, leaving him unable to exploit growing demand for website design. He admitted in the 2012 interview, “Sadly, I’m hopelessly color-blind so my first few attempts (at web design) were painful, even by 1997 standards.”
During later political campaigns, he would pay others for website design, not perform the work himself, according to campaign finance disclosures.
Site Street focused instead on web development (the back end of a site), and web hosting. But in the mid-2000s, Silicon Valley firms were investing billions of dollars to build sophisticated data centers and capture market share.
Small hosting firms like Flannigan’s increasingly were up against affordable, reliable providers like Bluehost (founded in 2003), WordPress (2003), Squarespace (2004), and Amazon Web Services (2006).
Flannigan also made the mistake of hiring more personnel than he could afford, admitting, “I hired people too quickly and kept them longer than was necessary.”
With the rise of social media and the growing importance of Google, Flannigan branched into social media consulting and search engine optimization.
But he was swimming against the tide. He had financed his business with debt from its inception. According to a Statement of Financial Information that he later filed during his 2014 campaign for office, he first borrowed from Wells Fargo in October 2002—a personal debt—then opened a business account with American Express in December 2002, the same month he incorporated Site Street.
The disclosure form doesn’t say exactly how much Flannigan borrowed or when, but more than a decade later, in 2013, he still owed between $20,000 and $60,000 in total on these two accounts, with an interest rate of 14 percent (financial disclosure forms lists debts within a range, and don’t require disclosure of specific amounts).
“I took some financial risks. All small business owners–especially very young ones–have ups and downs,” he said via email.
In May 2004, Flannigan borrowed again from Wells Fargo. His 2014 Statement of Financial Information doesn’t say whether this was a credit card, term loan, or some other type of financing, but by 2013, the year covered by the statement, he still owed $20,000 to $50,000, with an interest rate of 10.75 percent.
In 2006, he refinanced his Shasta Lane home, according to a 2006 real estate filing. The new note of $109,900 was larger than the original mortgage of $102,900.
Under the weight of student loan debts, mortgage debt, and business liabilities, Flannigan’s finances grew increasingly unsustainable. By 2009 at the latest, Site Street was under water and Flannigan needed cash.
“Jimmy never complained about the quality or timeliness of my work—he just quit paying me,” said a contract developer who worked for Site Street from 2006 to 2009, according to a Yelp post written by the developer.
The developer, identified on Yelp as “Gary M.,” said that he was owed $1,300. The Bulldog identified him through a LinkedIn profile as Gary Matthews, but was unsuccessful in reaching him. That this is the same person that left the review on Yelp is evidenced by the fact that Matthews wrote a recommendation for Flannigan published on both his and Flannigan’s LinkedIn pages.
Flannigan didn’t respond directly to a question about whether he had ever settled the contractor’s claim, instead saying generally, “I never shied away from my responsibilities and obligations.”
Around this time some of Flannigan’s other professional relationships began to suffer too. He had served as president of the Austin Gay and Lesbian Chamber since 2007. But in June 2009 The Austin Chronicle reported the board ousted him abruptly, citing mismanagement of the annual Pride festival.
Chad Peevy, the vice president who replaced Flannigan as president, didn’t respond to a request for comment about the chamber’s finances during Flannigan’s tenure. But in remarks to The Austin Chronicle in 2010, he suggested that there had been a lack of planning for Pride, and disputes with vendors.
The Bulldog asked Flannigan, “Were there any specific allegations of misappropriation of funds, inappropriate contracts, or other financial irregularities?” He responded, “There were never specific allegations sent to me.” He also pointed out that he was later restored to leadership of the chamber, and he cited various achievements in the role.
‘In a pinch at the moment’
Later in 2009 Flannigan borrowed thousands from his domestic partner at the time, Samuel Sone. They had a joint bank account, according to personal financial records obtained by the Bulldog. Sone admitted these records as evidence in a 2011 lawsuit (Case No. J-4-SC-11-000288). The first loan was for $2,500 for “business expenses” in October 2009, followed by another $2,000 loan for “business expenses” in December 2009.
For the first loan, Sone got a written commitment by email October 14, 2019 that Flannigan would repay over ten months in amounts of $250 per month. But by April 2010, Flannigan had made only one $250 repayment on his initial debt.
And the debts kept racking up. Samuel Sone paid a $2,058 cable bill for Flannigan in January 2010, bought office equipment for him, paid for a $410 UT football ticket, and covered his share of rent for $1,000 in February, according to lawsuit records.
Things went south between Flannigan and Sone soon thereafter. When Sone sought to recover the money, Flannigan stalled. He wrote in a July 2010 email, “Sorry…yeah, in a pinch at the moment. Pretty behind on things…almost as bad as it was in February.”
“Hopefully business should start to stabilize now that I’m not floating from house to house. Made it difficult to maintain productivity.”
But Sone was a generous lender, charging no interest and repeatedly giving Flannigan grace periods. (Sone didn’t respond to a request to comment for this story.) He replied to Flannigan’s email, “We can talk about it after things stabilize. Wish you the best!”
These emails, preserved in court records, were obtained by The Austin Bulldog through a public information request.
It was nine months before Sone approached Flannigan again. In an April 2011 email, he asked Flannigan to “come up with a payment schedule you believe is feasible,” and to sign a promissory note.
‘There are creditors in front of you’
Flannigan rejected the suggestion, replying a week later, “The whole thing makes me very uncomfortable. As much as it may delight you, my business continued to be very rough in 2010…to the point where I almost lost my house.”
“There are creditors in front of you that have to get paid first if I’m going to keep making any revenues at all. Thankfully it’s recovered in 2011 but it’s not a sudden turnaround…I don’t want to re-litigate our relationship or the breakup…but I also don’t have any cash to make you go away.”
Sone lost patience at that, and after several more attempts to get Flannigan to pay, on June 21, 2011, he filed suit with the Travis County Precinct 4 Justice of the Peace.
Flannigan filed a reply to the court on July 8, 2011, in which he denied that he had “agreed to pay back each and every item, nor that payment was to occur on a specific schedule.” He noted also that he never signed or agreed to any formal promissory note.
At the time, Flannigan was living at 902 Gardner Road, Unit 20, an East Austin property offering live-work studio spaces in a former warehouse, according to the court filing.
Flannigan and Sone appeared in court for a trial without jury on August 24, 2011. Precinct 4 Justice of the Peace Raul Gonzalez rendered judgment the same day, ordering Flannigan to pay $6,174 (the entire amount Sone had sued to recover), with a 5 percent rate of interest annually, plus $121 in court costs.
‘Defendant defaulted on the obligation’
Despite the court win, Samuel Sone wouldn’t get his money back for years to come. Flannigan was still underwater with other debtors—and he wasn’t paying them either.
“I feel like I need a banking consultant,” Flannigan wrote in an October 2011 comment on Facebook. He asked his followers for suggestions for how to choose a local credit union, saying, “I want to switch all my banking to a local credit union.”
In Facebook posts on October 5 and 21, 2011, he railed at Wells Fargo, saying he had been unfairly charged an overdraft fee, and complaining that the bank had “sold (my student loan) to some faceless company without my permission.”
As Flannigan soured on the banks, the banks soured on Flannigan. He disclosed in a candidate filing (Statement of Financial Information) covering the year 2013, that a portion of his debt—between $10,000 and $20,000—was transferred to CACH LLC. This is a company that buys bad debts and doesn’t originate its own loans.
Court documents obtained separately by The Austin Bulldog show that that debt stemmed from loans he had taken from FIA Card Services, a subsidiary of Bank of America, which then were transferred to CACH LLC.
In a court filing, the debt collector showed that it acquired the loan from Bank of America on April 26, 2012, the month after the bank canceled Flannigan’s credit card.
In a petition in the Williamson County Court at Law 4, attorneys for CACH LLC stated, “On or about 30 days after 12/27/2011 Defendant defaulted on the obligation to make monthly payments on the credit card account, and the card was subsequently canceled. The entire balance on the credit card account is presently due and payable in full.”
When Bank of America canceled Flannigan’s card, in March 2012, he owed $16,026 on the account, according to a credit card statement submitted to the court as evidence.
The outcome of this litigation, initially filed in 2014 (Case No. 14-0676-CC4), wouldn’t be clear until 2017. Initially, a judge dismissed the suit for want of prosecution. But the plaintiff refiled the suit under a different case number (Case No. 15-1077-CC4), and won.
Mortgages, credit card bills, student loans
In the meantime, the future city council member persisted with his business.
He claimed on his 2014 Statement of Financial Information, filed when he first ran for the District 6 City Council seat, that Site Street generated $50,000 to $75,000 in income in 2013. He listed only one major client—and also took on new debt. The Texas Medical Association paid him at least $25,000 that year, according to a 2014 Personal Financial Statement.
That was Flannigan’s only contract that year worth $5,000 or more.
On September 28, 2013, Flannigan incurred a personal debt of between $20,000 and $25,000 from Velocity Credit Union. That loan coincided with the purchase of a new Fiat. Two days after securing the loan, on September 30, 2013, he posted a photo of himself on Facebook at Austin’s Nyle Maxwell Fiat dealership, writing, “Never thought I would, but finally bought a new car.”
He still owed $75,000 to $100,000 on his Shasta Lane home mortgage, which by then was owned by Bank of America.
On top of that he owed a personal debt to Wells Fargo carrying a hefty interest rate of 14 percent. His 2014 SFI listed this debt in the range of $1 to $10,000, though his 2014 PFS put it at $10,000 to $24,999. (Statements of Financial Information are required by City Code and Personal Financial Statements are required by state law.)
Flannigan also still hadn’t repaid Samuel Sone. And a decade after getting his master’s degree, he still owed $20,000 to $25,000 in student loans to Wells Fargo.
And those were just the personal debts.
Flannigan’s business liabilities were somewhere between $25,000 and $60,000 split between three firms: Wells Fargo, American Express, and Marlin Leasing, according to the September 2014 PFS, which covered the prior year. His SFI filed in August 2014 put the amount at more $40,000 but less than $110,000.
His business debt to Wells Fargo was costing him 10.75 percent in annual interest, according to the SFI, and American Express was charging 14 percent.
Loses election and court case
In the meantime, Flannigan decided to take time away from his struggling web business to campaign for office, launching a bid for city council in the spring of 2014 for the November 2014 election that would implement geographic representation for council members.
In a five-way general election November 4, 2014, Flannigan made the runoff with 24 percent of the District 6 votes, just 27 fewer than Don Zimmerman. But he lost to Zimmerman by 191 votes in the December 16, 2014 runoff.
The new year saw Zimmerman installed in the city council seat that Flannigan had coveted—and he took a hard fall back to reality.
Though Flannigan had raised more than $88,000 in campaign contributions, he apparently was having less success running his business and keeping creditors at bay.
According to a credit card bill dating to January 2015, Flannigan’s minimum payment due on just a single credit card—an American Express business card—topped $2,800. Flannigan paid nothing, according to bank records submitted as court evidence.
Another bill of $3,886 fell due by March 12. By the spring, his interest charge topped $700 per month, and he wasn’t servicing the debt at all.
In July 2015, American Express Bank sued Flannigan in Williamson County Court at Law 4, seeking a judgment for the full credit card balance of $33,029. (Cause No. 15-1077-CC4.)
On his 2014 Personal Financial Disclosure, Flannigan had listed his American Express card as a business liability of Site Street. But in fact the account was jointly in his name.
That put his personal assets on the hook in case of default, even if his business declared bankruptcy.
Site Street never sought bankruptcy protection, according to PACER, the filing system for federal court records. Flannigan neither replied to the court citation issued against him nor filed any kind of reply. When asked about it, Flannigan said, “I have met my financial obligations without ever declaring bankruptcy.”
County Court at Law Four Judge John McMaster rendered a default judgment in April 2016 for the sum of $33,029, plus all costs of the court proceeding. After that, American Express placed a judgment lien on Flannigan’s house.
Next in line was CACH LLC, which filed suit in December 2015 (Case No. 15-1820-CC4), seeking a judgment for the same debt claim that it had originally pursued in 2014. It won a default judgment in May 2017—five months into Flannigan’s term as city council member.
The same judge presided, and rendered a default judgment ordering Flannigan to pay $16,712. Staking a claim to a piece of the Shasta Lane property, CACH LLC filed an abstract of the judgment in Williamson County’s property records.
‘We cut the debt down by at least half’
By now Flannigan was no longer living at the Shasta Lane property, which is in unincorporated Williamson County. He had moved into an apartment in northwest Austin on Anderson Mill Road—a necessary step to qualify for city council.
Flannigan collected rent from the Shasta Lane property, which helped cover the cost of the mortgage, but he had turned to an ex-neighbor for help in managing it.
In a phone interview, Shane Dayton told the Bulldog that he runs a residential contracting business and he has housed some of his employees in the Shasta Lane home. “I pay his mortgage—Jimmy Flannigan’s mortgage—I pay every month. And I collect a check for the rent,” he said.
Dayton has known Flannigan for a long time and is listed on both Flannigan’s oldest and newest PFS disclosures as a source of rental income. But in fact Dayton is more than just a tenant—he not only manages Flannigan’s property but also says that he paid off some of Flannigan’s creditors.
Dayton has wanted to buy the Shasta Lane property for some time, he said, and he agreed to pay Flannigan’s creditors in order to lift liens on the home and expedite the closing of a deal.
That would make Dayton a creditor to Flannigan in his own right. But in his 2020 PFS, covering his financial activity for 2019, Flannigan did not disclose Dayton as a creditor. Dayton explained in an interview, “I was heavily invested in this property, I had made improvements, I’ve got people who are living there…so what happened was, Jimmy still had two more liens.
“I hired a lawyer and we negotiated these judgments, which had sat over there forever, and I negotiated down to like half of their cost,” he said. “And I paid them. And I paid them so that I could have these things removed from the title so that I could close the deal. So Jimmy took that out as a debt, and now he’s paying me every month for that, starting back about six months ago.”
One of the debts that Dayton paid was to American Express Bank, which had won a judgment against Flannigan. “That $33,000 was substantially reduced, but yes, that is satisfied. But we settled for less than that. There was another one for like $24,000 that was brought down considerably as well.”
“So we cut the debt down by at least half and then paid them, and then Jimmy and I have a promissory note to pay me back for that money.”
The promissory note was for $25,000, to be paid in $595 installments monthly, Dayton said. The loan is interest-free unless Flannigan misses payments.
“The promissory note equaled the amount of the two payoffs that I made, in addition to my lawyers fees,” Dayton said.
Asked whether he had had any doubts about lending to Flannigan, given that Flannigan had dishonored other debts, Dayton replied, “Of course I did. But I was over a barrel already. This was something I had been working on for five or six years.”
Moreover, Dayton felt invested in the property, and hoped that Flannigan would give it to him at a good price. Given that he is a contractor, he could fix it up.
“The reason I lent him the money was not because he was a worthy (borrower),” Dayton said. “He’s not—he’s a terrible (borrower), and he doesn’t pay his debts, and there are liens and judgments against him. It’s awful.”
“The house has served my employees very well. They’re very, very blessed and happy there, so I don’t want to disturb that,” Dayton said. “I’m just hoping eventually it pans out… if not, I’m not going to lose any sleep over it.”
Dayton disclosed that he collects about $100 more per month from rents from the tenants than he pays for the mortgage, but also noted, “Jimmy doesn’t give me any money for the upkeep or anything else.”
Dayton’s account is confirmed in part by public records, which show that American Express Bank released its judgment lien in November 2019. Flannigan himself also confirmed his relationship with Dayton, telling the Bulldog, “Shane Dayton was my neighbor and is a friend. He has been making payments as part of an agreement to sell the house to him.”
He didn’t mention his debt to Dayton. Flannigan’s promissory note is dated December 31, and per PFS instructions, he should have disclosed “each person or financial institution” he owed more than $1,000 “at any time during the calendar year.”
Flannigan’s finances stabilize
Though Flannigan remains indebted, his financial situation appears to have improved in recent years, according to a variety of public records.
In 2016, he mounted his second—ultimately successful—bid to win the council seat for District 6. As his political prospects brightened, so too did his financial situation.
Sometime prior to his election win, Flannigan was hired by the Texas law firm McGinnis Lochridge, where he worked as a web developer, according to two public records: a 2016 Statement of Financial Information and a Federal Election Commission donation receipt.
The law firm lobbies at various levels of government and its employees historically have been large donors in state and local races. Thus far in the 2020 council elections, however, only one McGinnis Lochridge employee has made a donation, a $250 contribution to Council Member Greg Casar’s reelection campaign.
Flannigan didn’t respond to a question about how long he worked at McGinnis Lochridge. But confirmed, “To make ends meet, I worked for McGinnis Lochridge in the IT department.”
Samuel Sone got his money back in 2016, with interest, for a total payment of $7,868. He filed a Release of Judgment Lien, lifting a nearly five-year old encumbrance on the sale of the Shasta Lane property.
After assuming office in January 2017, Flannigan collected a salary from the city, helping to stabilize his finances. His current council salary is $79,934 and it will rise to $81,536 when the new fiscal year starts October 1, 2020.
With a stable income, he began investing in securing his own political future, loaning his campaign $1,515 in 2018 and $3,180 in 2019, according to campaign finance reports. His July 15, 2020, campaign finance report shows $4,695 in outstanding loans.
He is also repaying Shane Dayton, who noted, “He’s paying me monthly…I have money deposited monthly.” A list of payment activity in the Zelle banking app, shown to the Bulldog, confirms this.
Now running for reelection, Flannigan still describes himself in campaign materials as a “small business owner.” But Site Street no longer has a website, a Facebook page, or even a legal existence. The Texas Secretary of State in August 2017 involuntarily terminated the corporation for failure to continuously maintain a registered agent or registered office address as required by law.
Practically the only thing about Site Street still in existence is the debt: the firm still owes $10,000 to $25,000 to Wells Fargo and $10,000 to $25,000 to American Express, according to the council member’s 2020 Personal Financial Statement.
Asked whether Site Street ceased operations several years ago, Flannigan told the Bulldog, “I maintained a few clients but haven’t taken on a new client since the first campaign in 2014.”
He called the 2017 termination of Site Street by the Secretary of State a “paperwork error that was later corrected. I did terminate the S corp structure this year.”
But that’s not what public records show.
It was the state government—not Flannigan—that terminated the corporation, according to SOSDirect, an online database of business records maintained by the Texas Secretary of State.
The last document filed for Site Street is an August 29, 2017 “Certificate of Involuntary Termination.” The certificate states that Site Street Inc. “has failed to maintain a registered agent or registered office address in this state as required by law (and) that the entity has been given not less than 90 days notice of its neglect delinquency or omission by certified mail. It is therefore ordered that the…entity be involuntarily terminated without judicial ascertainment.”
Links to related documents:
American Express Bank FSB v. James Flannigan, Cause No. 15-1077-CC4, filed July 25, 2015 (93 pages)
CACH LLC vs. James T. Flannigan, Cause No. 14-0676-CC4, filed May 14, 2014 (26 pages)
CACH LLC vs. James T. Flannigan A/K/A Jimmy, Cause No. 15-1820-CC4, filed December 11, 2015 (34 pages)
Certificate of Involuntary Termination of Site Street Inc., August 29, 2017 (1 page)
Deed of Trust for James T. Flannigan for $102,900 at 12505 Shasta Lane, Austin, July 25, 2000 (17 pages)
Deed of Trust for James T. Flannigan for $109,900 at 12505 Shasta Lane, Austin, April 28, 2006 (14 pages)
Default Judgment, Cause No. 15-1077-CC4, April 6, 2016 for $33,028.72 (2 pages)
Default Judgment, Cause No. 15-1820-CC4, May 4, 2017 (2 pages)
American Express Bank Plaintiff’s Satisfaction of Judgment, Cause No. 15-1077-CC4 November 8, 2019 (2 pages)
Promissory Note executed by James T. Flannigan for $25,000 payable to Shane Dayton, December 31, 2019 (2 pages)
Release of Judgment Lien by Samuel Sone, August 18, 2016 (1 page)
Samuel Sone v. James Flannigan, Cause No. J-4-SC-11-000288, filed June 27, 2011 (69 pages)
Site Street Inc. Articles of Incorporation, December 23, 2002 (4 pages)
Site Street Inc. Certificate of Involuntary Termination, August 29, 2017 (1 page)
Statement of Financial Information of James Flannigan, August 25, 2014 (6 pages)
Williamson Central Appraisal District 2020 record for 12505 Shasta Lane, Austin (2 pages)
Links to related Bulldog coverage:
Council candidates have voting records too, September 18, 2020
Developer dollars flow to favored candidates, August 27, 2020