diff --git a/app/furniture/tobias.rb b/app/furniture/tobias.rb
new file mode 100644
index 000000000..0dd845ca6
--- /dev/null
+++ b/app/furniture/tobias.rb
@@ -0,0 +1,2 @@
+class Tobias
+end
diff --git a/app/furniture/tobias/beneficiary.rb b/app/furniture/tobias/beneficiary.rb
new file mode 100644
index 000000000..422e4a7fd
--- /dev/null
+++ b/app/furniture/tobias/beneficiary.rb
@@ -0,0 +1,10 @@
+class Tobias
+  class Beneficiary < ApplicationRecord
+    self.table_name = "tobias_beneficiaries"
+
+    belongs_to :trust, inverse_of: :beneficiaries
+
+    has_many :payments, inverse_of: :beneficiary
+    has_many :payouts, through: :payments
+  end
+end
diff --git a/app/furniture/tobias/payment.rb b/app/furniture/tobias/payment.rb
new file mode 100644
index 000000000..394c759c0
--- /dev/null
+++ b/app/furniture/tobias/payment.rb
@@ -0,0 +1,10 @@
+class Tobias
+  class Payment < ApplicationRecord
+    self.table_name = "tobias_payments"
+
+    belongs_to :payout, inverse_of: :payments
+    belongs_to :beneficiary, inverse_of: :payments
+
+    monetize :amount_cents
+  end
+end
diff --git a/app/furniture/tobias/payout.rb b/app/furniture/tobias/payout.rb
new file mode 100644
index 000000000..e2b3fbb43
--- /dev/null
+++ b/app/furniture/tobias/payout.rb
@@ -0,0 +1,20 @@
+class Tobias
+  class Payout < ApplicationRecord
+    self.table_name = "tobias_payouts"
+
+    belongs_to :trust
+    has_many :beneficiaries, through: :trust
+    has_many :payments, inverse_of: :payout, dependent: :destroy
+
+    monetize :amount_cents
+
+    def issue
+      return if payments.present?
+
+      per_beneficiary_amount = (amount / beneficiaries.count)
+      beneficiaries.each do |beneficiary|
+        payments.create_with(amount: per_beneficiary_amount).find_or_create_by(beneficiary: beneficiary)
+      end
+    end
+  end
+end
diff --git a/app/furniture/tobias/trust.rb b/app/furniture/tobias/trust.rb
new file mode 100644
index 000000000..357c690fd
--- /dev/null
+++ b/app/furniture/tobias/trust.rb
@@ -0,0 +1,8 @@
+class Tobias
+  class Trust < ApplicationRecord
+    self.table_name = "tobias_trusts"
+
+    has_many :beneficiaries, inverse_of: :trust, dependent: :destroy
+    has_many :payouts, inverse_of: :trust, dependent: :destroy
+  end
+end
diff --git a/db/migrate/20240127063826_create_tobias_payouts.rb b/db/migrate/20240127063826_create_tobias_payouts.rb
new file mode 100644
index 000000000..ad6eadffb
--- /dev/null
+++ b/db/migrate/20240127063826_create_tobias_payouts.rb
@@ -0,0 +1,27 @@
+class CreateTobiasPayouts < ActiveRecord::Migration[7.1]
+  def change
+    create_table :tobias_trusts, id: :uuid do |t|
+      t.timestamps
+    end
+
+    create_table :tobias_beneficiaries, id: :uuid do |t|
+      t.references :trust, type: :uuid, foreign_key: {to_table: :tobias_trusts}
+
+      t.timestamps
+    end
+
+    create_table :tobias_payouts, id: :uuid do |t|
+      t.monetize :amount
+      t.references :trust, type: :uuid, foreign_key: {to_table: :tobias_trusts}
+      t.timestamps
+    end
+
+    create_table :tobias_payments, id: :uuid do |t|
+      t.references :payout, type: :uuid, foreign_key: {to_table: :tobias_payouts}
+      t.references :beneficiary, type: :uuid, foreign_key: {to_table: :tobias_beneficiaries}
+      t.monetize :amount
+
+      t.timestamps
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index c1fdcaeb2..c52f70b69 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -333,6 +333,38 @@
     t.index ["slug", "client_id"], name: "index_spaces_on_slug_and_client_id", unique: true
   end
 
+  create_table "tobias_beneficiaries", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.uuid "trust_id"
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["trust_id"], name: "index_tobias_beneficiaries_on_trust_id"
+  end
+
+  create_table "tobias_payments", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.uuid "payout_id"
+    t.uuid "beneficiary_id"
+    t.integer "amount_cents", default: 0, null: false
+    t.string "amount_currency", default: "USD", null: false
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["beneficiary_id"], name: "index_tobias_payments_on_beneficiary_id"
+    t.index ["payout_id"], name: "index_tobias_payments_on_payout_id"
+  end
+
+  create_table "tobias_payouts", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.integer "amount_cents", default: 0, null: false
+    t.string "amount_currency", default: "USD", null: false
+    t.uuid "trust_id"
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["trust_id"], name: "index_tobias_payouts_on_trust_id"
+  end
+
+  create_table "tobias_trusts", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+  end
+
   create_table "utility_hookups", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.uuid "space_id"
     t.string "name", null: false
@@ -368,4 +400,8 @@
   add_foreign_key "rooms", "media", column: "hero_image_id"
   add_foreign_key "space_agreements", "spaces"
   add_foreign_key "spaces", "rooms", column: "entrance_id"
+  add_foreign_key "tobias_beneficiaries", "tobias_trusts", column: "trust_id"
+  add_foreign_key "tobias_payments", "tobias_beneficiaries", column: "beneficiary_id"
+  add_foreign_key "tobias_payments", "tobias_payouts", column: "payout_id"
+  add_foreign_key "tobias_payouts", "tobias_trusts", column: "trust_id"
 end
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 24c3d8ae7..23a18427c 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -1,6 +1,7 @@
 require "faker"
 require "pundit/rspec"
 require "simplecov"
+require "money-rails/test_helpers"
 
 SimpleCov.start do
   enable_coverage :branch
diff --git a/spec/tobias/beneficiary_spec.rb b/spec/tobias/beneficiary_spec.rb
new file mode 100644
index 000000000..1bb9a325a
--- /dev/null
+++ b/spec/tobias/beneficiary_spec.rb
@@ -0,0 +1,15 @@
+require "rails_helper"
+
+RSpec.describe Tobias::Beneficiary, type: :model do
+  describe "#trust" do
+    it { is_expected.to belong_to(:trust).inverse_of(:beneficiaries) }
+  end
+
+  describe "#payments" do
+    it { is_expected.to have_many(:payments).inverse_of(:beneficiary) }
+  end
+
+  describe "#payouts" do
+    it { is_expected.to have_many(:payouts).through(:payments) }
+  end
+end
diff --git a/spec/tobias/factories/beneficiary_factory.rb b/spec/tobias/factories/beneficiary_factory.rb
new file mode 100644
index 000000000..b330f1abb
--- /dev/null
+++ b/spec/tobias/factories/beneficiary_factory.rb
@@ -0,0 +1,4 @@
+FactoryBot.define do
+  factory :tobias_beneficiary, class: "Tobias::Beneficiary" do
+  end
+end
diff --git a/spec/tobias/factories/payout_factory.rb b/spec/tobias/factories/payout_factory.rb
new file mode 100644
index 000000000..f027e7300
--- /dev/null
+++ b/spec/tobias/factories/payout_factory.rb
@@ -0,0 +1,7 @@
+require_relative "trust_factory"
+
+FactoryBot.define do
+  factory :tobias_payout, class: "Tobias::Payout" do
+    association(:trust, factory: :tobias_trust)
+  end
+end
diff --git a/spec/tobias/factories/trust_factory.rb b/spec/tobias/factories/trust_factory.rb
new file mode 100644
index 000000000..7fd94abab
--- /dev/null
+++ b/spec/tobias/factories/trust_factory.rb
@@ -0,0 +1,4 @@
+FactoryBot.define do
+  factory :tobias_trust, class: "Tobias::Trust" do
+  end
+end
diff --git a/spec/tobias/issuing_payouts_system_spec.rb b/spec/tobias/issuing_payouts_system_spec.rb
new file mode 100644
index 000000000..d5f7dd05e
--- /dev/null
+++ b/spec/tobias/issuing_payouts_system_spec.rb
@@ -0,0 +1,23 @@
+require "rails_helper"
+require_relative "factories/trust_factory"
+require_relative "factories/beneficiary_factory"
+
+# @see https://github.com/zinc-collective/tobias/issues/11
+RSpec.describe "Tobias: Issuing a Payout", type: :system do
+  scenario "Issuing a `Payout` to multiple `Beneficiaries`" do # rubocop:disable RSpec/Capybara/FeatureMethods,RSpec/ExampleLength
+    trust = create(:tobias_trust)
+    beneficiaries = create_list(:tobias_beneficiary, 10, trust:)
+    visit(polymorphic_path(trust.location))
+    click_link("New Payout")
+    fill_in("Amount", with: 250_00)
+
+    click_button("Create Payout")
+
+    click_button("Issue Payout")
+
+    expect(page).to have_content("$25.00 Payments Issued to 10 Beneficiaries")
+    beneficiaries.each do |beneficiary|
+      expect(page).to have_content("#{beneficiary.name} $25.00 Pending")
+    end
+  end
+end
diff --git a/spec/tobias/payment_spec.rb b/spec/tobias/payment_spec.rb
new file mode 100644
index 000000000..19607f969
--- /dev/null
+++ b/spec/tobias/payment_spec.rb
@@ -0,0 +1,11 @@
+require "rails_helper"
+
+RSpec.describe Tobias::Payment, type: :model do
+  describe "#payout" do
+    it { is_expected.to belong_to(:payout).inverse_of(:payments) }
+  end
+
+  describe "#amount" do
+    it { is_expected.to monetize(:amount) }
+  end
+end
diff --git a/spec/tobias/payout_spec.rb b/spec/tobias/payout_spec.rb
new file mode 100644
index 000000000..cbb4af317
--- /dev/null
+++ b/spec/tobias/payout_spec.rb
@@ -0,0 +1,63 @@
+require "rails_helper"
+require_relative "factories/payout_factory"
+require_relative "factories/beneficiary_factory"
+
+RSpec.describe Tobias::Payout, type: :model do
+  describe "#payments" do
+    it { is_expected.to have_many(:payments).inverse_of(:payout).dependent(:destroy) }
+  end
+
+  describe "#beneficiaries" do
+    it { is_expected.to have_many(:beneficiaries).through(:trust) }
+  end
+
+  describe "#amount" do
+    it { is_expected.to monetize(:amount) }
+  end
+
+  describe "#issue" do
+    it "issues a Payment to each Beneficiary for their share of the #amount" do
+      payout = create(:tobias_payout, amount_cents: 150_00)
+
+      beneficiaries = create_list(:tobias_beneficiary, 10, trust: payout.trust)
+
+      payout.issue
+
+      beneficiaries.each do |beneficiary|
+        expect(beneficiary.payments).to exist(amount_cents: 15_00)
+      end
+    end
+
+    context "when the Payout#amount does not divide evenly" do
+      it "rounds down so that it can" do
+        payout = create(:tobias_payout, amount_cents: 3_33)
+
+        beneficiaries = create_list(:tobias_beneficiary, 2, trust: payout.trust)
+
+        payout.issue
+
+        beneficiaries.each do |beneficiary|
+          expect(beneficiary.payments).to exist(amount_cents: 1_66)
+        end
+      end
+    end
+
+    context "when running twice" do
+      it "does not issue multiple payouts, even when beneficiaries are added" do
+        payout = create(:tobias_payout, amount_cents: 100_00)
+
+        create_list(:tobias_beneficiary, 2, trust: payout.trust)
+
+        payout.issue
+
+        create(:tobias_beneficiary, trust: payout.trust)
+
+        # ActiveRecord appears to be caching the `payout.beneficiaries` results
+        # Reload busts that cache.
+        payout.reload
+
+        expect { payout.issue }.not_to(change(payout.payments, :count))
+      end
+    end
+  end
+end
diff --git a/spec/tobias/trust_spec.rb b/spec/tobias/trust_spec.rb
new file mode 100644
index 000000000..1ae161b9b
--- /dev/null
+++ b/spec/tobias/trust_spec.rb
@@ -0,0 +1,11 @@
+require "rails_helper"
+
+RSpec.describe Tobias::Trust, type: :model do
+  describe "#benificiaries" do
+    it { is_expected.to have_many(:beneficiaries).inverse_of(:trust).dependent(:destroy) }
+  end
+
+  describe "#payouts" do
+    it { is_expected.to have_many(:payouts).inverse_of(:trust).dependent(:destroy) }
+  end
+end