United States Court of Appeals
                             For the Eighth Circuit
                         ___________________________

                                 No. 19-3051
                         ___________________________

                              United States of America

                         lllllllllllllllllllllPlaintiff - Appellee

                                            v.

                                   Jovan J. Denson

                       lllllllllllllllllllllDefendant - Appellant
                                       ____________

                     Appeal from United States District Court
                 for the Western District of Missouri - Springfield
                                  ____________

                             Submitted: April 17, 2020
                               Filed: July 22, 2020
                                  ____________

Before SMITH, Chief Judge, BENTON and KOBES, Circuit Judges.
                              ____________

SMITH, Chief Judge.

       Jovan J. Denson pleaded guilty to conspiracy to distribute 1,000 grams or more
of heroin, see 21 U.S.C. §§ 841(a)(1), (b)(1)(A), 851; distribution of heroin, see 21
U.S.C. §§ 841(a)(1), (b)(1)(C), 851; possession of heroin, see 21 U.S.C. §§ 841(a)(1),
(b)(1)(B), 851; and money laundering, see 18 U.S.C. § 1956(a)(1)(B)(i). The district
court1 sentenced Denson to 292 months’ imprisonment. Denson argues that the
district court procedurally erred in calculating his sentence and that his sentence is
substantively unreasonable. We affirm.

                                      I. Background
       In early 2016, officers in Springfield, Missouri, began investigating an increase
in heroin trafficking. Eventually, officers confronted a seller, Amy Mitchell, who
identified Denson as one of her sources. After a few controlled buys, officers
requested and obtained multiple wiretap warrants for Denson’s phones. The wiretaps
intercepted calls and texts of Denson selling heroin to or with several individuals,
including Mitchell, Brian Brown, Edward Smith, Earl Jones, Deanna Miller, and
Claude Davis.2 Police stopped and searched a car driven by Denson’s suspected drug
courier. They also searched Denson’s home. These searches led to the seizure of
1,485 grams of heroin.

       After his arrest, Denson pleaded guilty to several counts arising out of his drug
activity. The presentence investigation report (PSR) described the conspiracy as
involving either 25,153 or 28,000 grams of heroin and recommended a base offense
level of 34. See U.S.S.G. § 2D1.1(c)(3). It also recommended a two-level
criminal-livelihood enhancement and a four-level organizer-or-leader enhancement.
See

Denson objected to the base offense level
and the enhancements.




      1
      The Honorable Stephen R. Bough, United States District Judge for the
Western District of Missouri.
      2
       While out of jail on bond, Davis died of a heroin overdose. Davis also sold
heroin to Benjamin Goodman, who sold to Shawn Smith. Smith died from opioid
abuse and had heroin in his system when he died.

                                          -2-
      At the sentencing hearing, the government called four witnesses to support the
PSR’s recommendations. These included three of Denson’s customers and an officer
who investigated the conspiracy.

      Mitchell testified that she purchased drugs from Denson and another individual
working for Denson called “Cuz.” Mitchell did not recall exact dates but stated she
began buying from Denson before November 2016 and stopped in May 2017. As for
quantities, she began purchasing one to three grams from Denson at a time. This
increased to 10 to 20 grams at a time.

       The government also called Brown, who was Mitchell’s boyfriend. The two
often made drug purchases together. Brown first purchased from Denson in late 2014
or early 2015. He began purchasing from him again around March 2016. Initially,
Brown purchased “grams here and there.” Sent. Tr. at 25, United States v. Denson,
No. 6:17-cr-03077-SRB-1 (W.D. Mo. Oct. 15, 2019), ECF No. 515. Brown stated that
he bought two to five grams per day for the first four to six months. A little before
Christmas in 2016, he began purchasing much larger quantities—“approximately 20”
(but “more like 30 to 40”) grams a day.

This continued until May 2017.

       Smith testified that he purchased from Denson for 10 to 12 months. For the first
five months, he only bought one or two grams a day. There were periods of a week
or two at a time, however, when Smith could not contact Denson. Over the next
four-or-five-month span, Smith increased his buys to two and then five grams a day.
By the final month or month and a half, Smith purchased 20 grams every day or every
other day. Smith also testified that, on one occasion, Denson had a woman in a blue
van deliver drugs for him.

       Lastly, the government called Officer Nick Mittag. Mittag testified that officers
intercepted calls and texts from Denson’s cell phones from April 4, 2017, to April 28,
2017, and from May 10, 2017, to May 16, 2017. Mittag reviewed the calls and texts

                                          -3-
and compiled a document (“Exhibit 3”) that chronicled the date, buyer, and amount
of drugs involved for each referenced transaction. If he was uncertain as to the
quantity, Mittag either placed a lower amount or left the quantity blank.

      Mittag also conducted surveillance of Denson. Based on that intelligence, he
believed Denson was not employed and spent his time at home or selling drugs.
Mittag admitted, however, that he did not observe Denson every day and that Denson
went to school to get his HVAC certification.

        Mittag testified that officers seized 780 grams from Denson’s suspected courier
and roughly half that amount from bushes outside of Denson’s home. They found the
latter after Denson directed his girlfriend to remove the drugs. Mittag claimed another
individual provided Denson’s stash house. Officers also found $11,000 on Denson
during a stop and search when Denson was traveling back from Chicago.

       In light of this evidence, the district court reduced Denson’s base offense level
to 32. Specifically, the court believed the customers’ testimonies indicated that the
final month-and-a-half was the peak of Denson’s activity, and Exhibit 3 supported a
finding that 1,000 grams of heroin were sold over that period. Based on the total
evidence, the district court found that the whole 15-month conspiracy involved 3,000
to 10,000 grams. See U.S.S.G. § 2D1.1(c)(4).

       Next, the court overruled Denson’s objection to the recommended
criminal-livelihood enhancement. That enhancement required proof that (1) Denson
made more than $14,500 from his criminal activity, and (2) the criminal activity
constituted Denson’s primary source of income. The court found those requirements
were satisfied because Denson lacked a job; Denson used $9,500 in cash to purchase
an Audi; and officers seized $11,000 from Denson when they arrested him.




                                          -4-
       Third, the court applied a three-level manager-or-supervisor enhancement
instead of the PSR’s recommended four-level organizer-or-leader enhancement. See

The court found the conspiracy involved five or more participants and
that Denson directed at least one. See

court’s rulings on drug quantity and enhancements reduced the
Guidelines range from 292 to 365 months’ imprisonment to 210 to 262 months’
imprisonment. However, the district court varied upward to 292 months’
imprisonment. The court based the variance on the deleterious effects of heroin use,
including local deaths during the criminal activity.

                                   II. Discussion
      Denson claims that the district court erred in calculating his base offense level;
applying a two-level criminal-livelihood enhancement and a three-level
manager-or-supervisor enhancement; and imposing a substantively unreasonable
sentence.

                              A. Base-Level Calculation
       Denson contends that his base offense level was set too high because of
erroneous drug quantity figures. The PSR recommended a base offense level of 34,
stating that the conspiracy involved at least 10,000 grams but less than 30,000 grams
of heroin. Denson argued a base level of 30 should apply; he admitted that the
government seized 1,485 grams but objected to higher suggested amounts. At
sentencing, the district court sustained, in part, Denson’s objection. It found that the
offense involved between 3,000 grams and 10,000 grams and reduced the base
offense level to 32. On appeal, Denson argues that there was insufficient evidence to
support a finding that the conspiracy involved even 3,000 grams.




                                          -5-
       “Drug quantity determinations are factual findings, which we review for clear
error, applying the preponderance-of-the-evidence standard.” United States v. King,

, 809 (8th Cir. 2018) (internal quotation omitted). The sentencing court’s
“factual determinations will stand unless the decision is unsupported by substantial
evidence, is based on an erroneous view of the applicable law, or in light of the entire
record, we are left with a firm and definite conviction that a mistake has been made.”
United States v. Colton, 

, 348 (8th Cir. 2014) (per curiam) (internal
quotation omitted).

       When appropriate, the district court may estimate drug quantity. “When the
amount of narcotics seized by the government does not reflect the scale of the drug
trafficking offense, . . . the court shall approximate the quantity of the controlled
substance and may consider, for example, similar transactions in controlled
substances by the defendant.” United States v. Sterling, 

, 442 (8th Cir.
2019) (internal quotations omitted). “The court may make a specific numeric
determination of quantity based on imprecise evidence . . . .” United States v. Roach,

, 413 (8th Cir. 1998).

       Given these precedents, few defendants appealing estimated drug quantity
findings “have cleared the high bar of clear error review.” 

.
“That is because, almost invariably, the district court finding was based upon
testimony at trial or at an evidentiary sentencing hearing—usually by suppliers or
customers of the defendant—that provided the court with a reasonable basis to make
a specific numeric determination of quantity based on imprecise evidence.”

omitted).3


      3
        The government argues that if there was error, Denson invited it at the
sentencing hearing. In his sentencing memorandum, Denson objected to the PSR and
said that the base level should be 30 rather than 34. At the hearing, Denson initially


                                          -6-
       Denson admits that law enforcement seized 1,485 grams. But he contends that
the evidence does not show that the conspiracy involved the additional 1,515 grams
required to support a base level of 32. We disagree. The district court may make a
“numeric determination of quantity based on imprecise evidence.” 

. For instance, in Colton, we upheld a quantity determination that was derived
“from records introduced at trial showing that individuals wired a total of $334,494
as part of the drug 

. “The Government divided the
$334,494 amount by $20, which represents the highest amount paid for a pill based
on testimony at trial, to arrive at a total of 16,725 pills.”

“classified 7,172
of those pills as Oxycontin pills and 9,553 as Opana pills based on the trend in sales
of each drug that police observed during the dates of the conspiracy.”

the district court to adopt those findings.

United States v. Moore, we allowed estimates that were based on drug
customers’ testimonies. 798 F. App’x 952, 958 (8th Cir. 2020) (per curiam). There,
“[o]ne witness testified that she purchased between one-half to one gram of heroin
from [the defendant] every day for two years.”

second witness testified
that he purchased one to two grams of heroin every day for two years. Using the
conservative numbers, the court found that the first witness had purchased 365 grams
from Johnson and that the second had purchased 730 grams.”

court’s
finding was determined not to be clearly erroneous.

the court could find a middle ground, which appears to refer to a base
level of 32. But Denson’s counsel later decided to “stick with my objections and
argue that we believe it’s a base offense level of 30.” Sent. Tr. at 61. Given that
retraction, we cannot say that Denson approved the district court’s base-level finding
and invited the error. See United States v. Mahler, 

, 815 (8th Cir. 1998)
(“The doctrine of invited error applies when the trial court announces its intention to
embark on a specific course of action and defense counsel specifically approves of
that course of action.” (internal quotation omitted)).


                                           -7-
       Here, the government offered similar estimations. The district court did not
clearly err in relying on them. The conspiracy ran from March 2016 to May 2017. At
sentencing, an officer testified that he intercepted some of Denson’s calls and texts
from April 4, 2017, to April 28, 2017, and May 10, 2017, to May 16, 2017. He then
created Exhibit 3, which indicated the date, buyer, and amount of drugs involved. All
told, Exhibit 3 attributed to Denson sales of 1,003 grams of heroin during those
periods.

       In addition, officers seized $11,000 during Denson’s arrest. Based on
testimony, that amount of cash was equivalent to 122.222 or 226.796 grams of heroin
at the time of arrest.4

      Three of Denson’s customers also testified at sentencing. Even giving Denson
a number of favorable inferences, these testimonies indicate that he sold the requisite
amount of heroin. These inferences included assuming that (1) Brown and Mitchell
always purchased together, (2) the buyers purchased every other day rather than every
day, and (3) the April and May sales were limited to those indicated in Exhibit 3. The
testimonies of these witnesses attributed to Denson over 1,300 grams during the
conspiracy’s first 13 months.5 When combined, these sources indicated that Denson


      4
      The officer testified that Denson sold heroin for $90/gram; at that rate,
$11,000 would buy 122.222 grams. Elsewhere, he testified that $11,000 could
purchase half a pound, which is approximately 226.796 grams.
      5
        Taken together, Brown and Mitchell testified that they purchased two grams
a day almost every day between March 2016 and December 2016. Assuming they
never exceeded that amount and really purchased every other day, they purchased 306
grams during that period. That calculation discounts increases that occurred in
December. Then, from January 1 to March 31, they purchased roughly 20 (but “more
like 30 or 40”) grams a day. Sent. Tr. at 27. Again, assuming that they only purchased
on half of the days during that time period, that would be an additional 900 grams.


                                         -8-
sold more than 3,000 grams of heroin during the conspiracy. And, it should be noted
that his total does not include amounts sold during the first 13 months to other
individuals mentioned in the PSR.

       In sum, the district court did not clearly err in finding that the conspiracy
involved between 3,000 and 10,000 grams of heroin and imposing a base offense
level of 32.

                        B. Criminal-Livelihood Enhancement
       Denson next claims that there was insufficient evidence to establish that he
derived a livelihood from his criminal activity. We review the district court’s factual
finding to the contrary for clear error. United States v. Berry, 

, 999 (8th
Cir. 2019).

       Sentencing courts may increase an offense level by two levels if “[t]he
defendant committed the offense as part of a pattern of criminal conduct engaged in
as a livelihood.” U.S.S.G. § 2D1.1(b)(16)(E). For the enhancement to apply, the
evidence must establish that (1) during any 12-month period, the defendant received
an income from the criminal activity that was 2,000 times the federal minimum wage,
and (2) during that 12-month period, the criminal activity was the defendant’s
primary occupation.

cmt. n.2.


Thus, those two purchased at least 1,206 grams from March 2016 to March 2017.
Smith testified that he purchased one-to-two grams a day for five months, and
two-to-five grams a day for another five months, with additional increases during the
final month and a half. Assuming that (1) the last month and a half of that time period
is covered by Exhibit 3, (2) he always purchased the lesser amount, and (3) he only
bought every other day, Smith purchased about 77 grams during the first 5 months
and 105 grams during the last 3.5 months, a total of 182 grams. When combined,
those amounts equal 1,388 grams.


                                          -9-
       Denson argues that the government failed to establish either requirement.
Given the current minimum wage, the government had to prove that Denson “derived
more than $14,500 in income from his drug activity.” 

. Income
“refers to gross income, not net.”

Further, “a substantial cash
flow from criminal activity is sufficient evidence to satisfy the ‘income’
requirement.”

previously addressed similar arguments. In Berry, we upheld a
criminal-livelihood enhancement where “[t]he district court found that Berry wired
$22,000 for drugs in a single year, that he had no significant legitimate employment,
and that evidence suggested he had other large amounts of cash on hand.”

Given those findings, the district court’s enhancement “could not be clearly
erroneous.”

States v. Morris, there was testimony that the defendant had no
income. 

, 914 (8th Cir. 2015). But there was evidence “that he was
selling large quantities of methamphetamine every week, always paid his rent on
time, purchased a car for $13,300 in cash, paid cash for $14,000 worth of repairs and
improvements on his home, and purchased several businesses.”

Given
that record, we found that the district court did not clearly err in applying the
criminal-livelihood enhancement.

      Other circuits have reached similar conclusions. For example, the Second
Circuit has found that the “primary occupation” requirement satisfied based largely
on the market value of drugs sold. See United States v. Pristell, 

, 54–55
(2d Cir. 2019). And, the First Circuit found that there was insufficient evidence of
gainful employment where the defendant offered ambiguous letters indicating that he
had worked as a barber. United States v. Gordon, 

, 134–35 (1st Cir.
2017). The ambiguous letters could not overcome the inference that his “lucrative



                                         -10-
drug-trafficking activities during the twelve months at issue” provided his support.

      We affirm the district court’s application of the enhancement. The proof of
Denson’s non-employment income suffices. The government’s evidence shows that
Denson met the $14,500 threshold counting only his income for April and May 2017.
In April, Denson paid $9,500 in cash as a down payment for an Audi. See 

–15 (considering amount used for car purchase and home repairs). And
when he was arrested, Denson carried $11,000 in cash. Taken together, those sums
alone exceed the $14,500 threshold.6

       Additionally, at the time of his arrest, officers discovered 528 grams of heroin
on Denson’s property. Given that the value of heroin was $90 per gram, that heroin
had a street value of $47,520. See 

(considering the fair market
value of drugs). Also, the government tracker indicated that Denson entered
transactions involving 1,003 grams of heroin during April and May. That heroin’s
street value was $90,270. In short, the government offered sufficient evidence to
indicate that Denson’s criminal activity yielded significantly more than $14,500 gross
income.

     In determining his primary occupation, we may compare evidence of gainful
employment against the financial evidence discussed above. See 

        Denson says that we cannot consider those sums because the government
failed to show (1) that the money put down on the Audi was his and (2) that the
money on his person was tied to drug use. However, in his plea agreement, he
stipulated that those sums were tied to drug sales. We have discretion to rely on such
stipulations. See United States v. Dailey, 

, 748 (8th Cir. 1990) (“[T]he
court may, in its discretion, rely upon stipulations between the government and the
defendant in determining the facts relevant to sentencing.”).


                                         -11-
1000; 

–35. Denson alleges that he made $4,500 a month
working at a carpeting company and as a carpenter. But Mittag testified that he
regularly observed Denson during the investigation, and Denson was either at his
house or selling drugs. In other words, Denson was not observed engaging in gainful
employment. The investigator admitted that he did not constantly observe Denson and
that Denson was in school to obtain a HVAC certificate. Nonetheless, beyond
unsupported claims, there is no evidence in the record that Denson had
income-yielding employment during the conspiracy. Weighing his claims against his
criminal activity’s income, the district court did not clearly err. See 

(disregarding claims that the defendant was a barber as unsupported, especially
when weighed against his drug income). The district court did not clearly err by
enhancing Denson’s sentence under U.S.S.G. § 2D1.1(b)(16)(E).

                    C. Manager-or-Supervisor Enhancement
        The PSR recommended a four-level enhancement for Denson’s role in the
conspiracy. Denson objected. The district court sustained the objection in part, but
still found that Denson was a manager or supervisor, and applied a three-level
enhancement. Denson argues that the evidence did not even support that
enhancement.

        The Guidelines recommend a three-level enhancement if (1) “the defendant
was a manager or supervisor (but not an organizer or leader),” and (2) “the criminal
activity involved five or more participants.” U.S.S.G. § 3B1.1(b). “The government
bears the burden of proving by a preponderance of the evidence that the aggravating
role enhancement is warranted.” United States v. Gaines, 

, 427 (8th Cir.
2011). The district court’s application of this Guideline is reviewed de novo, while
its factual findings are reviewed for clear error.

“We construe the terms
‘manager’ or ‘supervisor’ broadly under U.S.S.G. § 3B1.1 . . . .” United States v.
Bolden, 

, 990 (8th Cir. 2010) (per curiam) (internal quotation omitted).



                                         -12-
“The enhancement may apply even if a defendant managed or supervised only one
person in a single transaction.” United States v. Reyes-Ramirez, 

, 1148
(8th Cir. 2019).

       In Bolden, we found that the district court did not clearly err in applying the
enhancement where the defendant “directed the activities of a co-conspirator during
an attempted traffic stop in an effort to evade police detection of some 

. And in Moore, we upheld the enhancement’s application where the
defendant’s sister delivered drugs to buyers who placed orders with the defendant.
798 F. App’x at 959.

       Denson managed or supervised more than one other person. Testimony showed
that Denson directed his girlfriend to conceal drugs, much like the defendant who
directed a co-conspirator to conceal drugs in Bolden. Denson’s direction satisfies the
“managed” requirement. But Denson did more. Evidence showed that Denson used
another person’s residence as his stash house. Also buyers testified that, on a few
occasions, after placing orders with Denson, a man known as “Cuz” and “a woman
in a blue van” made deliveries to them. Like Moore, that conduct supports an
inference that the individuals making the deliveries worked for Denson. In addition,
officers stopped one of Denson’s suspected couriers. During that stop, the officers
discovered 780 grams of heroin in her vehicle.

      In summary, the district court heard testimony (1) that Denson directed
individuals to hide, store, sell, and transport heroin, and (2) that the criminal activity
involved more than five people. Therefore, it did not err in finding that Denson
managed or supervised the criminal activity and applying a three-level enhancement.

                        D. Substantive Reasonableness
      Denson’s final argument is that the district court imposed a substantively
unreasonable sentence. We review the reasonableness of a sentence under an



                                          -13-
abuse-of-discretion standard. United States v. Johnson, 

, 920 (8th Cir.
2010). “A district court abuses its discretion when it (1) fails to consider a relevant
factor that should have received significant weight; (2) gives significant weight to an
improper or irrelevant factor; or (3) considers only the appropriate factors but in
weighing those factors commits a clear error of judgment.” United States v. Feemster,

, 461 (8th Cir. 2009) (en banc) (internal quotations omitted). “We do not
require a district court to provide a mechanical recitation of the § 3553(a) factors
when determining a sentence. Rather, it simply must be clear from the record that the
district court actually considered the § 3553(a) factors in determining the sentence.”
United States v. Walking Eagle, 

, 659 (8th Cir. 2009) (internal quotation
omitted).

      Denson claims that the district court abused its discretion by (1) failing to
consider mitigating factors and (2) varying upward from the Guidelines range by 30
months.

       As for mitigating factors, Denson claims that the district court did not consider
his history of substance abuse, lack of parental guidance, upbringing in racially
concentrated poverty, and desire for treatment and change. We disagree. The relevant
sentencing factors were discussed in the court’s sentencing memorandum and at the
sentencing hearing. Based on that discussion and the court’s comments, we conclude
that the district court considered Denson’s mitigation evidence but found it an
inadequate counterweight to other considerations in § 3553(a). See 

. Therefore, the district court did not abuse its discretion in its review of
Denson’s proffered mitigating factors. See

the upward variance, the district court stated that it varied upward
because of the seriousness of the offense, highlighting heroin’s dangerousness and
the actual deaths of individuals connected to this case. That was not an abuse of
discretion. In United States v. Reif, a boyfriend distributed heroin to his 19-year-old



                                         -14-
girlfriend, and she died. 

, 1198 (8th Cir. 2019). Because of that death
and the defendant’s heroin use, the district court varied upward 75 months and
sentenced the defendant to 96 months’ imprisonment.

that variance was
reasonable.

Here, two individuals connected to the conspiracy died.
Aware of those deaths, the district court varied upward 30 months and sentenced
Denson to 292 months. Given the record, that variance makes sense.

       In sum, the district court adequately considered the mitigating factors and its
resulting sentence was reasonable. It did not abuse its discretion.

                                 III. Conclusion
      For the foregoing reasons, we affirm the judgment of the district court.
                      ______________________________




                                        -15-