0. Milewski's "Category Theory for Programmers"[0]
1. Goldblatt's "Topoi"[1]
2. McLarty's "The Uses and Abuses of the History of Topos Theory"[2] (this does not require [1], it just undoes some historical assumptions made in [1] and, like everything else by McLarty, is extraordinarily well-written)
3. Goldblatt's "Lectures on the Hyperreals"[3]
4. Nelson's "Radically Elementary Probability Theory"[4]
5. Tao's "Ultraproducts as a Bridge Between Discrete and Continuous Analysis"[5]
6. Some canonical machine learning text, like Murphy[6] or Bishop[7]
7. Koller/Friedman's "Probabilistic Graphical Models"[8]
8. Lawvere's "Taking Categories Seriously"[9]
From there you should see a variety of paths for mapping (things:Uncertainty) <-> (things:Structure). The Giry monad is just one of them, and would probably be understandable after reading Barr/Wells' "Toposes, Triples and Theories"[10].
The above list also assumes some comfort with integration. Particularly good books in line with this pedagogical path might be:
9. Any and all canonical intros to real analysis
10. Malliavin's "Integration and Probability"[11]
11. Segal/Kunze's "Integrals and Operators"[12]
Similarly, some normative focus on probability would be useful:
12. Jaynes' "Probability Theory"[13]
13. Pearl's "Causality"[14]
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[0] https://bartoszmilewski.com/2014/10/28/category-theory-for-p...
[1] https://www.amazon.com/Topoi-Categorial-Analysis-Logic-Mathe...
[2] http://www.cwru.edu/artsci/phil/UsesandAbuses%20HistoryTopos...
[3] https://www.amazon.com/Lectures-Hyperreals-Introduction-Nons...
[4] https://web.math.princeton.edu/%7Enelson/books/rept.pdf
[5] https://www.youtube.com/watch?v=IS9fsr3yGLE
[6] https://www.amazon.com/Machine-Learning-Probabilistic-Perspe...
[7] https://www.amazon.com/Pattern-Recognition-Learning-Informat...
[8] https://www.amazon.com/Probabilistic-Graphical-Models-Princi...
[9] http://www.emis.de/journals/TAC/reprints/articles/8/tr8.pdf
[10] http://www.tac.mta.ca/tac/reprints/articles/12/tr12.pdf
[11] https://www.springer.com/us/book/9780387944098
[12] https://www.amazon.com/Integrals-Operators-Grundlehren-mathe...
[13] http://www.med.mcgill.ca/epidemiology/hanley/bios601/Gaussia...
[14] https://www.amazon.com/Causality-Reasoning-Inference-Judea-P...
Machine Learning: The Art and Science of Algorithms that Make Sense of Data (Flach): http://www.amazon.com/Machine-Learning-Science-Algorithms-Se...
Machine Learning: A Probabilistic Perspective (Murphy): http://www.amazon.com/Machine-Learning-Probabilistic-Perspec...
Pattern Recognition and Machine Learning (Bishop): http://www.amazon.com/Pattern-Recognition-Learning-Informati...
There are some great resources/books for Bayesian statistics and graphical models. I've listed them in (approximate) order of increasing difficulty/mathematical complexity:
Think Bayes (Downey): http://www.amazon.com/Think-Bayes-Allen-B-Downey/dp/14493707...
Bayesian Methods for Hackers (Davidson-Pilon et al): https://github.com/CamDavidsonPilon/Probabilistic-Programmin...
Doing Bayesian Data Analysis (Kruschke), aka "the puppy book": http://www.amazon.com/Doing-Bayesian-Data-Analysis-Second/dp...
Bayesian Data Analysis (Gellman): http://www.amazon.com/Bayesian-Analysis-Chapman-Statistical-...
Bayesian Reasoning and Machine Learning (Barber): http://www.amazon.com/Bayesian-Reasoning-Machine-Learning-Ba...
Probabilistic Graphical Models (Koller et al): https://www.coursera.org/course/pgm http://www.amazon.com/Probabilistic-Graphical-Models-Princip...
If you want a more mathematical/statistical take on Machine Learning, then the two books by Hastie/Tibshirani et al are definitely worth a read (plus, they're free to download from the authors' websites!):
Introduction to Statistical Learning: http://www-bcf.usc.edu/~gareth/ISL/
The Elements of Statistical Learning: http://statweb.stanford.edu/~tibs/ElemStatLearn/
Obviously there is the whole field of "deep learning" as well! A good place to start is with: http://deeplearning.net/
http://www.amazon.com/Machine-Learning-Probabilistic-Perspec...
http://metaoptimize.com/qa/questions/186/good-freely-availab...