(chose this username in a moment of sourness 3 years ago and have regretted it ever since!)
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Most sub 2 hr oly people have ironman times well under 10. No one can do the work for you. Train your ass off, try not to neglect your family and job, and maybe if you are lucky it will come together for you.
Can I point out that many women go well under 10 for an Ironman and few go sub-2 for Olympic.
Wow - way too much to digest. We are actually pretty similar (but I’m now 37, doc, 2 kids in school now, etc.) and similar times (he is slightly faster as posted, especially in the water). First IM sub 10? Maybe at Florida if everything goes well, but he seems WAY to time oriented. He is only 34 - relax (I know the type - I am the type). Do the first IM and enjoy it and not stress about the time. Yes, sub 10 would be possible - but so is a DNF which could be devastating to his psyche. I’d do Lake Placid or a nice course first, then hammer out at Florida a “time” if that is what he wants.
I just helped a friend go 9:45 at IMFL this year (his 2nd IM - LP was his first) at age 40 (his goal was Kona) and he did NOT get in with a rolldown (damn Germans) 
His other times are almost exactly the same as your friend.
John should pick one of those goals but not both considering their proximity … training properly for a 10:00 IM in August may not be conducive to 2:00 OD race 1 month earlier. Not to say it couldn’t be done but a 2:00 race in July isn’t going to tell John anything about his ability to produce a sub 10:00 IM one month later.
Why not focus on one event this year and the other next year?
Best of luck!
The question is not whether he is going to be fit enough, but rather can he pace. I’ve known a handful of fast Oly athletes who walked the run on their first IM because they did not know how to reign in the watts on the bike. Assuming he can learn to pace correctly it is certainly achievable, but harder to do than pencil out.
That being said, I think he will have a hard time if he focuses on both goals. His Oly race would be right in the middle of his six week Ironman build. That could be a rather painful experiment.
I think it is possible it. I would recommend Going Long (haven’t read Fink’s book). As long as he realizes that nutrition may be his limiting discipline and practices it as part of his training he can be successful. As with any lofty goal, expert advice is a key, even if it is just a couple of hours of telephone consult to make sure the plan is good.
I thought I could nail my first IM, despite only being a 4:45 HIM in prior years. I did okay (didn’t nail it), but just a few small mistakes (that I think could have been preventable if I had gone with a little more coaching oversight) prevented me from probably being in the low 10:00 range. For the knowledgeable athlete I don’t think a lot of coaching is needed, but if you want to do something difficult right the first time, find someone who has been there already (which I did, just needed to get a little bit more guidance than I chose to pay for), or it may take two tries (as it will for me).
“Has read Don Fink’s book cover to cover 10 times”
This statement makes me think it is possible for him to break 10 hr. To be a good ironmaner (I think I made that word up) requires a slight amount of OCD, or a tolerance for the incredibly mundane…obviously he fits the bill.
I don’t know if there is a lesson to learn here but in my first year of triathlon I did a half ironman (tupper lake -hilly) and my time was 4:24. I thought I could break 10 and at Kona that year because everyone said 2xhalf+1hour=ironman… anyway I went 11:59. My dream blew up into a millioin pieces during the marathon and I am supposed to be a runner. The Ironman is a funny thing. Dave Scott says that he never focused on X-time during his races and I think there is a lot of wisdom to that.
Pace and getting nutrition right.
I posted this same question early this year. I went 10:57 in my first and wondered what it would take to get that to 9:57. In short, I over-trained my ass off for four months and got myself injured. I hobbled to the finish line and posted an 11:26 this year. Now I am off to get back surgery and will be laid up for awhile. I guess the only advice a newbie like me can give is to throw the goal time out the window because it takes the fun out of it and to make sure he can handle the amount of training it takes for a sub-10.
Pacing for sure. It is a bit of a mental game too. I was on target to break 10.00 in my first ironman (and second year of triathlon) but walked most of the last 10-11kms. I was feeling really good, and then my legs just went, began to walk the aid stations, and that was my ‘running’ over.
It’s doable based on the very brief details here:
Positives:
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He has 15 years of training behind him. This in my mind is HUGE. If he has been steady and consistant with this even if as you say it’s been a moderate amount, then this is a great base to operate from.
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The Olympic time is solid. There is a bigger connection between this and a great IM time than people thik. Many here and elsewhere seem to think that there is not much of a connection, but both races are nearly 100% aerobic. In fact it’s all aerobic!!
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Never run a marathon - that’s a good thing and I hope that he does not get it in his head that he has to run one beore his IM.
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Decent run fitness.
Negatives:
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There are a huge number of variables in training and racing an IM. Trick is to control as many of them as you can.
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The 1/2 IM time is a bit slow, but this maybe to the lack of longer training to date.
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As Rod said, don’t get too worked up about time. It’s OK to have a time goal, but keep it in the back ground, particularly on race day. Best to race the first IM from a conservitive stand-point and let the race come to you.
Just prescribed yourself some “medication” and you’ll be well on your way…
Thankyou everybody for the advice
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(chose this username in a moment of sourness 3 years ago and have regretted it ever since!)
You know you can change it in your profile… how about ‘eatmyshorts’