Roundtree v. Reynolds et al

Filing 56

ORDER signed by Judge J P Stadtmueller on 3/12/2025. 48 , 49 , and 52 Motions by non-party Donald Reynolds are DENIED as moot. 50 Defendants' Motion to Clarify Plaintiff's Settlement Proposal is DENIED as moot. CASE DISMISSED without prejudice for lack of subject matter jurisdiction. See Order. (cc: all counsel, via mail to Joshua Roundtree at Yazoo City FCI and to Defendants)(jm)

UNITED STATES DISTRICT COURT
EASTERN DISTRICT OF WISCONSIN
JOSHUA ROUNDTREE,
Plaintiff,
Case No. 23-CV-552-JPS

v.
MICHELLE REYNOLDS and
UNCAGED MINDS PUBLISHING,

ORDER

Defendants.

1.

INTRODUCTION
This matter, pending since May 2023, ECF No. 1, and in which both

sides proceed pro se, more appropriately belongs in state small-claims
court, but it has so far managed to remain in federal court, ostensibly on
diversity jurisdiction. ECF No. 22 at 3; ECF No. 44 at 8. Plaintiff Joshua
Roundtree (“Roundtree”) accuses Michelle Reynolds (“Reynolds”) and her
sole proprietorship Uncaged Minds Publishing (“UMP”) (together,
“Defendants”) of violating their contract to publish two of Roundtree’s
books, and he seeks to recover what he paid Defendants for this publication
deal plus his lost profits. See generally ECF No. 18.
Because both sides are unrepresented, the Court directed the parties
to submit all the evidence related to their claims so that the Court could
consider the entire record before it and “determine what further action is
warranted” in this case. ECF No. 44 at 15–16. The parties have done so.
Based on all the information before it, the Court concludes that it lacks

subject matter jurisdiction over the case and accordingly is constrained to
dismiss it without prejudice.1
2.

RELEVANT FACTS
The Court instructed the parties to exchange and submit copies of

the contract(s) that governed the alleged publication deal, “written
correspondence . . . relating to this transaction,” evidence of payments or
lack thereof, evidence of work Defendants completed for Roundtree, and
evidence supporting Roundtree’s contentions as to lost profits. Id. at 14–15.
The Court has reviewed the parties’ submissions pursuant to this directive,
together with the operative pleadings, and constructed the following
narrative of what happened between Roundtree and Defendants.
Roundtree is a federal prisoner. See ECF No. 18 at 1 (listing address
at federal correctional institution); see also Inmate Locator, FEDERAL BUREAU
OF PRISONS , available at https://www.bop.gov/inmateloc/ (last visited Mar.

12, 2025) (reflecting continued federal custodial status). UMP holds itself
out as a publisher and offers to distribute works authored by incarcerated
people like Roundtree. See ECF No. 47 at 4 (“[Defendants] took out an ad in
Kite Magazine, . . . advertis[ing] ‘self-publishing.’”). Reynolds is UMP’s sole
proprietor, meaning that Defendants are treated as one and the same for
legal purposes. ECF No. 44 at 5–6, 8.2

Non-party Donald Reynolds, see ECF No. 44 at 3–8 and 9–10, has filed
several motions. ECF Nos. 48, 49, and 52. Because Donald Reynolds is not a party,
has not been permitted to intervene in this case, and seeks relief that is not relevant
to the case at bar, those motions will be denied as moot. See ECF No. 44 at 3 (“The
Court has been drawn into what appears to be an interpersonal conflict between
Michelle Reynolds and Donald Reynolds . . . that has no immediate bearing on
[Roundtree’s] lawsuit.”); id. at 6–7 (detailing Michelle and Donald Reynolds’ state
divorce matter).
1

As the Court previously explained, “[w]hether Michelle Reynolds is
validly using the UMP moniker” notwithstanding the existence of a limited
2

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Roundtree claims that he signed a contract with Defendants to
publish two books he wrote while incarcerated. ECF No. 18 at 2, 4.
Defendants seem to agree that they had a two-book publishing contract
with Roundtree. ECF No. 36 at 1. The parties have submitted different
documents that they refer to as their contract, each of which contains
different terms.
Roundtree proffers as the parties’ contract a series of documents that
bear his and Reynolds’s signatures. ECF No. 45-1. That series of documents
shows the parties agreeing first to an “Exclusive Plat[in]um Publishing
Contract” by which Defendants would publish two of Roundtree’s books
for $900, with Roundtree to provide his own cover art and Defendants
offering no editing service on his novels. Id. at 2. Reynolds signed and dated
that document on July 13, 2020, and Roundtree signed and dated it on July
24, 2020. Id. The parties then renegotiated a “new contract,” id. at 4, by
which Defendants would still publish two of Roundtree’s books, again with
Roundtree providing his own cover art and Defendants not furnishing any
editing service, id. at 6. This version of the contract further specifies that
Defendants would offer Roundtree “the Plat[in]um package” for one book
and “the silver” package for his other book, resulting in a lower cost of
$800.00. Id. Roundtree signed and dated that document on July 27, 2020,
and Reynolds signed it on August 7, 2020. Id. Neither version of the contract
that Roundtree filed defines what a “Plat[in]um” or “Silver” publishing
package means or includes.

liability company with the same name, incorporated in Illinois and registered to
Donald Reynolds, “[is] not the subject[] of this lawsuit.” ECF No. 44 at 4, 6 n.2, and
7 & n.3.

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Defendants assert that they agreed to different terms with
Roundtree. They do not have any document signed by both parties, though;
they instead submit “a blank copy of [Defendants’] contract,” presumably
the standard contract it offers to all individuals interested in Defendants’
services. ECF No. 36 at 2. Defendants say that they agreed with Roundtree
that he would pay $699 for a two-book contract, id. at 1, and indeed the
unsigned, blank contract they submitted provides that Defendants’
“Platinum Package” costs $699. ECF No. 36-1 at 1.3 Platinum is apparently
one of four packages that Defendants offer, together with Silver, Gold, and
Diamond, which increase in price ($399, $499, and $999, respectively) and
which include increasingly more benefits such as cover design, promotional
materials, creation of social media accounts and websites on the author’s
behalf, editing, and typing. Id. The unsigned, blank contract further
provides that “[t]he price quoted is for books 285 pages or less” and that
“[n]o rewrites are allowed,” presumably after the point when the
manuscripts were submitted to Defendants. Id. at 3.
Defendants state that they sent Roundtree a blank copy of their
version of the contract (without saying when they allegedly sent it) but that
Roundtree never signed or returned it. ECF No. 36 at 1. Roundtree insists
that the blank contract that Defendants offer is not relevant because he
“NEVER agreed to [Defendants’] standard contract” and instead the parties
formed a “special contract.” ECF No. 45 at 2; see also ECF No. 47 at 1 (“The
agreement [Roundtree submitted] is signed by both parties, conflicting with

However, in a motion to dismiss which the Court denied without
prejudice, Defendants state that the parties agreed to a cost of $900. ECF No. 40 at
1; ECF No. 44 at 9. Though the Court disregards Defendants’ factual allegations in
that motion, the inconsistency is noteworthy—why don’t Defendants have their
story straight?
3

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. . . Reynolds misleading the courts into believing that we had any other
existing agreement.”). He acknowledges that Defendants emailed him the
above-referenced standard contract, but he contends they only did so “three
years after the real contract.” ECF No. 47 at 1 (citing ECF No. 47-1 at 13
(March 16, 2023 email from Reynolds to Roundtree enclosing same blank
contract as described above)). Defendants counter that Roundtree “picked
and chose” from the parties’ correspondence and “did not submit the
earlier messages where [they] sent out the standard contract.” ECF No. 50
at 2. But Defendants have not submitted documents substantiating when,
prior to March 2023, they sent such messages or their standard contract to
Roundtree.
Although it is not clear whether the parties were ever on the same
page about their respective obligations, they each accuse one another of
violating the terms of the contract in some way. See generally ECF Nos. 18
and 36.
Roundtree says Defendants breached the contract because, to date,
they have not published or finished editing his books and refuse to refund
his payments. ECF No. 18 at 5; ECF No. 45 at 1; id. at 2 (alleging that
Defendants “never even proofed book one” and “never finished the proof
of book two”). Defendants counter that Roundtree himself is the barrier to
publication. They say that Roundtree’s books are ready to be self-published
through Amazon Kindle Direct Publishing (“Amazon KDP”) but that
Roundtree has failed to get a trusted person outside of prison to activate the
Amazon account for him in order to permit Defendants to post the books
there. ECF No. 36 at 1–2; see also ECF No. 50 at 1.4 As to editing, Defendants

Neither version of the contract discusses the requirement that the author
designate a trusted person outside of prison to set up an Amazon KDP account for
4

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contend that they “did all the edits in book one” and completed the edits
they could in book two. ECF No. 47-1 at 38. They further argue that
Roundtree has caused or contributed to the delays in publication. See, e.g.,
ECF No. 36 at 1 (“[A]fter nearly five months of waiting we received
[communication from Roundtree].”); id. at 2 (noting that Roundtree
submitted rewrites even though standard contract does not permit them
and then “did not respond to [Defendants] again for nearly 8 months”).
Roundtree counters that draft manuscripts that he has received from
Defendants were riddled with errors, rendering them unfit for publication
as-is on Amazon KDP, and that Defendants are the source of the delay,
having at various times ceased communicating with him or updating him.
ECF No. 18 at 3; ECF No. 45 at 2; ECF No. 47 at 4–5.
For their part, Defendants say that Roundtree is in breach—or that
they at least had good reason not to publish his books or to delay doing
so—because he submitted manuscripts in excess of the purported
contractual 285-page limit. ECF No. 36 at 1. Roundtree denies agreeing to
any page limit, ECF No. 45 at 2, and says he informed Defendants of the
length of his manuscripts before he sent them in, ECF No. 47-1 at 37 (“YOU
them. Defendants state that they have this requirement because establishing such
an account “require[s] personal information that [Defendants] don’t need nor . . .
want to be responsible for.” ECF No. 36 at 1.
Roundtree told Defendants in April 2023 that he already “ha[s] a KDP
account ([in] [his] name),” with “all the necessary info . . . on there.” ECF No. 47-1
at 32. Defendants say essentially the same thing. ECF No. 36 at 2 (“I sent all his
files to the email [created for Roundtree] and sent [him] the login information for
the email account so he could have his family upload the books to Amazon [KDP]
when they completed the setup of the account.”). But Roundtree has indicated a
reluctance for Defendants to publish his work to Amazon KDP for him at this
point. ECF No. 51 at 1; see also ECF No. 47-1 at 32 (“My family/friends ARE NOT
publishers. YOU [were] paid to publish my books. NOT THEM! [T]hey have no
clue of how to up load [sic] a book.”).

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knew the page count because I told you.”); see also id. at 32 (“You could’ve
simply sent my money back when you [saw] the page count. YOU chose to
move forward with [the contract].”).5 Defendants deny that they knew or
that Roundtree informed them of the page count before they received his
manuscripts and state that they would not have contracted with Roundtree
at all if they knew the length of the manuscripts. ECF No. 36 at 1
(“Roundtree was asked on numerous occasions the page count of these
books. His response was, “not many.”); ECF No. 47-1 at 37.6
As for damages, Roundtree seeks the money he paid to Defendants,
which totals $900. ECF No. 47-1 at 19, 21, 23 (checks for $400, $400, and $100,
made out to one or both Defendants); id. at 30 (seeking refund from
Defendants of “the $900.00 I paid you to publish my book[s]”).7 He says that
he eventually “paid a new company to publish book one,” which “cost[]
[him] A LOT more money,” though he does not say how much, or seek this
amount in damages. ECF No. 47 at 5; ECF No. 46 at 2 (requesting as a
settlement option that Defendants publish book two only); see also ECF No.

Roundtree has not provided any documentation supporting the
contention that he informed Defendants of the length of his manuscripts at any
time before the above-cited March 2023 email.
5

It appears that, whatever the parties decided with respect to cover art and
design, this term of the parties’ agreement is no longer at issue. See ECF No. 36 at
1 (“Mr. Roundtree decided to pay additional fees to have [Defendants] complete
both cover designs for his books. . . . [W]e received two images that Mr. Roundtree
wanted to use . . . on his cover designs. We completed the designs and sent to Mr.
Roundtree for his approval.”); ECF No. 47 at 3 (“Copies of the original covers
submitted.” (citing ECF No. 47-1 at 25–26)).
6

Roundtree also still appears to seek $150 or $175 in damages because
Defendants promised to type a third manuscript for him but failed to do so. ECF
No. 22 at 3 (citing ECF No. 18 at 4, 6); ECF No. 47-1 at 41 (“You OWE me $150 just
from the manuscript you [were] paid to type and didn’t.”). Defendants appear to
admit this. ECF No. 47-1 at 30 (“[Y]ou are owed $150[] [f]or the typing job you
hired me to do, but we never received the manuscript.”).
7

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51 at 2 (rejecting Defendants’ settlement offer to publish both books because
“book one has changed” so “the works submitted to . . . Reynolds many
years ago CANNOT be used.”).
He further claims that he lost out on $100,000 in profits due to
Defendants not publishing his books. ECF No. 18 at 6. After accepting this
allegation as true at the complaint stage, ECF No. 22 at 3, the Court ordered
Roundtree to back it up with
[e]vidence . . . that supports his position that he lost $100,000
in profits when his books were not published—for example,
evidence that books Defendants have published make that
much money, or that similar books to those he has written
tend to garner that much profit[.]
ECF No. 44 at 14–15. Roundtree has not directly responded to this prompt,
but he speculates in his filings that his lost profits are high. ECF No. 45 at 1
(“Who knows, maybe I could have had an international best seller on my
hands.”); ECF No. 47 at 5 (“I personally value my manuscripts at
$100,000.00. . . . [W]ho’s to say that I cannot be the next Steinbeck, Patterson,
Grisham, Sheldon, Faulkner, King, Hemingway or at least Mosley. . . I could
have possibly earn[ed] MILLIONS!”).
3.

LAW & ANALYSIS
The Court ordered the parties to submit relevant evidence so that it

could determine whether it could “resolve this case on the written
submissions alone” as opposed to holding a hearing or taking testimony.
ECF No. 44 at 15. The Court noted the possibility that, based on the evidence
submitted, it may “dismiss[] this case for lack of subject matter jurisdiction
(if Plaintiff cannot satisfactorily prove his proposed damages) or grant[]
summary judgment to one party or another.” Id. at 15–16; id. at 9 (“The
Court will revisit th[e] [subject matter jurisdiction] determination after
discovery has been completed . . . .”).
Page 8 of 13

“When there are no issues of material fact in dispute, a district court
may grant summary judgment on its own motion—as long as the . . .
part[ies] [are] given notice and an opportunity to come forward with [their]
evidence. Osler Inst., Inc. v. Forde, 333 F.3d 832, 836 (7th Cir. 2003) (citing
Celotex Corp. v. Catrett, 477 U.S. 317, 326 (1986) and Goldstein v. Fidelity and
Guar. Ins. Underwriters, Inc., 86 F.3d 749, 750 (7th Cir. 1996) (“The party
against whom summary judgment is entered must have notice that the
court is considering dropping the ax on [it] before it actually falls.”)).
The Court gave notice to the parties of the possibility that summary
judgment could be entered, but after review of the record, the Court is not
able to grant summary judgment to either side. The parties do not agree,
and the Court cannot determine, (1) what the contract required them each
to do or (2) whether each party has actually done what it was required to
do. A prime example of this is the alleged page limit in the version of the
contract that Defendants proffer. If the parties never actually agreed to this
page limit, then it seems that Defendants have no leg to stand on in using
the length of the manuscripts to justify delays or failure to publish
Roundtree’s work. But resolving with finality the issue of whether the
parties actually agreed to such a page limit would require the Court to
“weigh credibility . . . or resolve swearing contests” between Roundtree and
Defendants, which it cannot do at summary judgment. Flowers v. Renfro, 46
F.4th 631, 636 (7th Cir. 2022) (citing Payne v. Pauley, 337 F.3d 767, 770 (7th
Cir. 2003)).
What is clear and undisputed on the record before the Court, though,
is that Roundtree has failed to establish with acceptable evidence that his
alleged damages meet the amount in controversy jurisdictional threshold.

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28 U.S.C. § 1332(a) (providing for federal diversity jurisdiction “where the
matter in controversy exceeds . . . $75,000”).
“Generally the amount in controversy claimed by a plaintiff in good
faith will be determinative on the issue of jurisdictional amount, unless it
appears to a legal certainty that the claim is for less than that required by
the rule.” NLFC, Inc. v. Devcom Mid-America, Inc., 45 F.3d 231, 237 (7th Cir.
1995) (citing St. Paul Mercury Indem. Co. v. Red Cab Co., 303 U.S. 283, 289
(1938) and Gibbs v. Buck, 307 U.S. 66, 72 (1939)). “[I]f the court’s jurisdiction
is challenged as a factual matter by . . . the court”—as it was in this case,
ECF No. 44 at 9—the plaintiff must establish that jurisdiction exists by
“competent proof,” which “has been interpreted to mean a preponderance
of the evidence or ‘proof to a reasonable probability that jurisdiction
exists.’” Id. (quoting McNutt v. Gen. Motors Acceptance Corp. of Ind., 298 U.S.
178, 189 (1936) and Gould v. Artisoft, Inc., 1 F.3d 544, 547 (7th Cir. 1993) and
citing Grafon Corp. v. Hausermann, 602 F.2d 781, 783 (7th Cir. 1979)); see also
14B CHARLES ALAN WRIGHT & ARTHUR R. MILLER, FEDERAL PRACTICE AND
PROCEDURE JURISDICTION AND RELATED MATTERS § 3702 (5th ed. 2024) (“The
legal-certainty concept appears equivalent to a conclusion that as a matter
of law the jurisdictional amount cannot be recovered or, stated differently,
no reasonable jury could award that amount.”).
“We may look to post-filing events, including production of
evidence during discovery, to the extent they ‘clarify what the plaintiff was
actually seeking’ at the beginning of the case.” Sykes v. Cook Inc., 72 F.4th
195, 209–10 (7th Cir. 2023) (quoting Carroll v. Stryker Corp., 658 F.3d 675,
680–81 (7th Cir. 2011) and citing Brand Servs., L.L.C. v. Irex Corp., 909 F.3d
151, 155 (5th Cir. 2018)); Brand Servs., 909 F. 3d at 155 (explaining that when
the complaint does not make it “facially apparent” that more than $75,000

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is in controversy, the court may look to “summary judgment-type
evidence” (quoting St. Paul Reinsurance Co. v. Greenberg, 134 F.3d 1250, 1253
(5th Cir. 1998))).
The Court earlier suggested to Roundtree specific examples of
evidence that might be acceptable to demonstrate his lost profits. ECF No.
44 at 15. Roundtree had many months to gather and submit such evidence
as to lost profits, but he has failed to do so. He insists that he has lost profits
of $100,000 or more, but nothing he has submitted would permit the Court
or any reasonable jury to infer this. This is not a judgment on the quality of
Roundtree’s books, which the Court has not read. Rather, it simply means
that Roundtree’s speculation that his books could be bestsellers and his
personal valuation of his work are not sufficient to establish, for purposes
of diversity jurisdiction, that he likely lost $100,000 in profits because his
books were not published.
The Court therefore can no longer consider Roundtree’s asserted lost
profits in determining whether the amount in controversy is met in this
case. The only damages Roundtree has shown with competent proof are the
$900 in publication fees that he paid to Defendants plus the $150 or $175 he
paid to Defendants to type a third manuscript for him, see supra note 7.
These amounts total no more than $1,075, which is far short of the $75,000
amount in controversy required to establish and maintain diversity
jurisdiction. 28 U.S.C. § 1332(a). Accordingly, the Court is constrained to
dismiss this case without prejudice for lack of jurisdiction. Fed. R. Civ. P.
12(h)(3) (“If the court determines at any time that it lacks subject-matter
jurisdiction, the court must dismiss the action.”). Dismissal without
prejudice means that Roundtree can refile the lawsuit, if he so chooses, but
for the reasons explained herein, he will not be able to do so in federal court.

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4.

CONCLUSION
For the reasons stated above, the Court must dismiss this case

without prejudice. Defendants’ motion to clarify Roundtree’s settlement
proposal, ECF No. 50, will be denied as moot, as will all motions filed by
non-party Donald Reynolds.
Accordingly,
IT IS ORDERED that non-party Donald Reynolds’s motions, ECF
Nos. 48, 49, and 52, be and the same are hereby DENIED as moot;
IT IS FURTHER ORDERED that Defendants Michelle Reynolds
and Uncaged Minds Publishing’s motion to clarify Plaintiff Joshua
Roundtree’s settlement proposal, ECF No. 50, be and the same is hereby
DENIED as moot; and
IT IS FURTHER ORDERED that this case be and the same is hereby
DISMISSED without prejudice for lack of subject matter jurisdiction.
The Clerk of Court is directed to enter judgment accordingly.
Dated at Milwaukee, Wisconsin, this 12th day of March, 2025.
BY THE COURT:

____________________________________
J. P. Stadtmueller
U.S. District Judge

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This Order and the judgment to follow are final. A dissatisfied party may
appeal this Court’s decision to the Court of Appeals for the Seventh
Circuit by filing in this Court a notice of appeal within thirty (30) days of
the entry of judgment. See Fed. R. App. P. 3, 4. This Court may extend
this deadline if a party timely requests an extension and shows good
cause or excusable neglect for not being able to meet the thirty-day
deadline. See Fed. R. App. P. 4(a)(5)(A). Moreover, under certain
circumstances, a party may ask this Court to alter or amend its judgment
under Federal Rule of Civil Procedure 59(e) or ask for relief from
judgment under Federal Rule of Civil Procedure 60(b). Any motion under
Federal Rule of Civil Procedure 59(e) must be filed within twenty-eight
(28) days of the entry of judgment. The Court cannot extend this deadline.
See Fed. R. Civ. P. 6(b)(2). Any motion under Federal Rule of Civil
Procedure 60(b) must be filed within a reasonable time, generally no more
than one year after the entry of the judgment. The Court cannot extend
this deadline. See id. A party is expected to closely review all applicable
rules and determine what, if any, further action is appropriate in a case.

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