The race director told us at the beginning of Stage 5, “so like the Pioneers, the last obstacle you face on the trail are getting around the Cascades. Here you see Mt. Bachelor on the left and the 3 Sisters to the right. So let’s get this over with, the scenery was amazing and the riding weather perfect for my (shared with 400 other riders) Oregon Trail Gravel Grinder adventure. I’d be lying a bit if I actually didn’t call both spectacular. Over the course of 320 miles, the picture there was about as much clouds as we saw. Yet the temps were consistently in the high 60s to mid 70s, perfect riding weather. So from that perspective it was awesome. And we saw rivers, resevoirs and forests to go with the almost ever present mountains, traversing over 22,000 feet of vertical over the 5 days.
So before I get to some stories, suffering and lessons learned, here’s a taste of some more of the amazing scenery along the way.
Pretty cool. The five days were definitely the most challenging week I have ever had on a bike, at least in a long time (Maybe 1988 touring Illinois for 5 days in 90 degree heat and 90% humidity matched it, but that was a LONG time ago and I was a heck of a lot younger!)
So before I get to the lessons, three more pics… First me fresh at the starting line on day 1…
and putting a good but dirty face on it after day 4:
and then pretty much how I felt for a week after the race here back at home:
When I got home, Dr Scott Frey, who I have had the privilege to strike up an online connection with, and who I look forward to meeting soon in person at the Bovine Classic in October and I had a quick linked in chat that looked like this:
So now, with a week of reflection, here are my top learnings from a week of Sand and Suffering…
Lessond 1: Doing Hard Things SO WORTH IT. I won’t go so far as to say the week was life changing, but it probably was. It was HARD! I was challenged but physically and mentally, and even though I did the non-competitive “Settler” version of the ride, as I decided early on day two that my shoulder was hurt just enough that I should “settle” on 320 miles and 23K ft, vs. the Pioneer version 360 and 30K, days 4 and 5 were by far the two hardest single days I have ever done on a bike. It wasn’t the distance or the vertical, which were hard, but the technical nature of the terrain was beyond my experience, and the days were long, hard and demanding. But in the end, I finished with just a few scrapes and a sore shoulder, and with a huge sense of accomplishment and satisfaction of taking on a very hard challenge and succeeding at it, or in Oregon trail terms, I did not “Die of Dysentery”. Plus as a bonus, maybe next time it is the Pioneer length. SO WORTH IT!
Learning 2: Performance Has Many Dimensions, or at Least 3! First off, I want to recognize my other 400 riders as amazing and talented humans. From stage 1 winner and eventual 4th place pro Cam Jones and his racing partner Seamus, pictured with me here in camp after day 1, the level of overall level of fitness, skill and grit was off the charts.
And it wasn’t just the pros, but the almost 200 50+ riders, who woke up each day and battled the sand, the rocks and themselves. I was consistently around the middle of the pack of the “Settlers” and am in awe of the entire group of riders.
OK, so, here’s my lesson. I came into the event as fit as I think I possibly could have been. I also gutted out several hours on days 2 and 4 when my shoulder felt like it was on fire at time and was “popping” when I moved it, and the that my pure fear on some of the technical descents, and I think I managed my mental attitude well, so on the grit side, I give myself a job well done. Now, I mentioned the technical skills, yeah, mine need a lot of work. If performance = Fitness * Grit * Skills, and each were on a 1-10, I’d give myself a 10 on fitness, a 9 or so on grit, and honestly like a 3 on skill on day 1, improving to maybe a 5 on day 5, for an average of 4. So using my formula, I’d rate my performance as a 360/1000. Lots of room for improvement. I do realize with no mountain biking experience, and just 2 full years on my gravel bike, 4 aint so bad. And honestly, I think if I had tried this ride a year ago, I either have been on the Dysentery van to Bend by the end of day 2. So, I guess I need that skills coaching and work for sure before I take this on again.
Lesson 3 – To Make Your Enemy Your Friend, Just Change Directions! – We had quite a bit of sand on Day 2, or so I thought. I joked that they should have named the ride the Oregon Train Beach Grinder, not the Gravel Grinder. But on that day, the terrain where the sand was was mostly flat, and the sand, as learned on day 5, was pretty chill. At mile 5 of day 5 however, we hit a BRUTAL soul sucking 2 mile rolling uphill of at least 6 inch deep black cinder sand. Pretty much everyone, regardless of skill level was eventually bogging down and doing some hike-a-bike. The sand ended, and was quickly replaced by a rock garden bone jarring descent, followed by more of both. Eventually, at mile 38 we reached a 11.7 mile 2900 ft climb, and while the first 2/3 was mercifully paved, it was steep at 8% or so, and directly into the sun. It was the first time it felt very hot on the ride. At mile 8, we turned left onto a shallower climb. We crested at mile 12 at about 6700 feet, which only meant 1 thing, a 3000 ft gravel descent into our finish line at Bend. And the descent was quite sandy. And soon, I actually got the hang of it and realized the sand was my friend on this descent, and I did my best technical descending of the week ( I also took my only real fall, but that was on double track switching lanes and sliding out. So sand, my enemy, finished as my friend, at least when going downhill.
Overall the Oregon Trail Gravel Grinder was an amazing experience. It was well run, great people, many other stories, and definitely the hard thing I had hoped for. Next up for me is the Steamboat Gravel blue course, my unfinished business from last season when I “DNF’d” due to heat and cramps. I will say, I am feeling more confident and more ready than ever to take SBT Grvl on successfully in 6 weeks and finally don the finisher’s hat that I have refused to put on (my friend “grabbed me one”) for the last year. Oh, and check it out, I did earn this t-shirt –
Happy trails, may all your hard things be as awesome as this one was for me!
I’ve never really liked the old ‘Painkiller vs. Vitamin’ selling metaphor. And I’ve been repeatly drawn to this topic, maybe because I hear this old meme so often. It’s too simplistic and often becomes an excuse for sales teams when they miss their numbers, with the claim that ‘Customers only buy painkillers, not vitamins.’
Well, this morning, I had an aha moment—that this metaphor is all about Pain and neglects the aspect of Benefit. We need a second dimension. We need to diagnose the market’s pain points more precisely and prescribe a course of action that delivers more substantial, varied benefits.
So I grabbed the nearest napkin, sketched this out, like what I saw, and jammed it into a readable sketch in Google Slide. Here’s what I came with, call it the Pain-Benefit Matrix.
This matrix is a more nuanced approach, recognizing the varying intensities of pain but, crucially, also considering the types of benefits that solutions can provide. It’s not just about whether a solution acts as a painkiller or a vitamin; it’s about understanding the tactical to strategic benefits these solutions bring to the table. After all, painkillers and vitamins/preventative cures are huge industries, so in some ways, the metaphor is broke from the start.
Each quadrant of this matrix offers a distinct value proposition, reflecting both the nature of the customer’s pain and the strategic benefit of the solution. Let’s debunk the myth that customers are only interested in painkillers and explore how each type of solution can be compelling, and the implications of each type on B2B Sales and Marketing approaches.
The Tactical “Painkiller” for Acute/Isolated Pain: Immediate Relief Sure, painkillers are vital for addressing immediate, acute pains, akin to a headache. They are tactical, offering quick and direct relief. But the benefit here isn’t just relief; it’s the ability to quickly overcome an obstacle and maintain operational flow. It’s like taking Tylenol to get rid of that headache.
Sales Implications:
Emphasize rapid problem resolution.
Utilize a consultative sales approach to understand and address the specific pain point.
Marketing Implications:
Craft targeted campaigns that highlight the immediate benefits and quick action.
Use case studies and testimonials to demonstrate quick wins.
The “Vitamin” for Chronic/Systemic Pain: Preventative or Systemic Care The value of “vitamins” or other treatments for chronic, systemic issues, is often overlooked or negated when thinking about B2B sales. Like statins to treat high cholesterol or Vitamin C to prevent scurvy, these solutions offer strategic, long-term benefits, contributing to the sustained health and resilience of a business. Far from being unnecessary, they are crucial in preventing larger problems down the line.
Sales Implications:
Engage in longer sales cycles with a focus on strategic change and gains
Educate customers on the long-term benefits and ROI of a proactive solution.
Marketing Implications:
Develop content that speaks to long-term benefits and overall business health.
Use educational materials to raise awareness of the systemic issues and the curative power of the product.
The Strategic “Cure” for Acute/Isolated Pain: Comprehensive Solution Cures go beyond the immediate relief provided by painkillers by offering a strategic, long-term solution to acute problems, addressing the root cause and preventing recurrence. This quadrant highlights the need for solutions that not only solve the problem but also integrate into the client’s broader strategic goals.
Sales Implications:
Position the solution as a strategic investment that addresses the root cause.
Tailor presentations to show the comprehensive and lasting benefits of the solution.
Marketing Implications:
Develop more content that simplifies and explains the strategic advantages of the product in customer terms.
Highlight long-term success stories and post-solution transformation.
The Transformative “Superpower” for Chronic/Systemic Pain Superpowers are transformative solutions for chronic, systemic issues. They offer a strategic advantage that transcends mere problem-solving, enabling new capabilities or significant improvements in performance. They are strategic, not just in resolving current issues but in setting a new direction for the company’s future. Think of this like the transformative power of a new diet, exercise and sleep routine!
Sales Implications:
Employ a challenger sales strategy driven by a leading story of change and strategic advantage
Focus on the transformative impact of the solution on the customer’s business operations and results
Marketing Implications:
Craft a visionary narrative that aligns with the customer’s aspirations.
Leverage thought leadership and industry influencers to drive the message of transformation.
This expanded view challenges the notion that customers are only interested in immediate solutions to acute problems. It emphasizes the importance of understanding the customer’s pain in its entirety and aligning solutions with both their immediate needs and their long-term strategic goals.
The Pain-Benefit Matrix not only broadens our perspective beyond the limited view of ‘painkillers’ but also highlights the diverse range of benefits that we can offer to customers. It’s time to move past the outdated metaphor and embrace a more nuanced and comprehensive approach.
My son Owen is a high school club volleyball player. While he isn’t near the tallest, at almost 5 ft 10in and still growing, he definitely is the giant of our house. And his height DEFINITELY comes from Mom’s size. Owen plays setter. Setter is, as I have learned, the quarterback of the team. The setter gets more “touches” than any other player, and while the hitters get most of the glory, without a good set, there is no ball to kill.
What in the heck does this have to do with Category strategy? Well, let me explain a bit more about Volleyball teams. The typical squad has about 12 or so players. Of those, two are typically setters, maybe three. This depends on whether the team is playing a 5-1 or a 6-2 rotation. Without getting into the gory details, the first number is the number of hitters that rotate around, the second number, the number of setters. So if the coach plays a 5-1, only one setter plays, and usually they will roster just 2. In a 6-2, two setters play and you might have 3 on the roster. You see, in competitive volleyball, you play a position, players are categorized and put into a roster slot based on the position they play.
This brings me to a conversation I recently had with Owen after this seasons tryout process, where Owen ended in a great spot on a good team, but not quite on his first choice roster.
Owen: “Why would Coach X pick Player Y over me, I’m better than him”
Dad: “Well are you like a ton better”
Owen: “Well Y is good, I’m just better”
Dad: “Here’s what I think Owen, Y has been playing on Coach X’s team for like 3 seasons. His parent is team parent, and he knows the other players, and there’s trust and a two way commitment. He’s part of the system! Coach X would have to think you are like 100X better than Y to give you that spot…”
So, here you go. You are a startup. You say – “I am such a better Category X than established player(s) Y. Those buyers would be crazy not to pick me over them…”
But I say, “the buyer has a relationship with Y. Y is part of their “team” already. Y is embedded in their business or life. Are you really 100x better?”
Now the good news is you have another choice. Don’t be a better X than Y. Be a “NewCat”. Unlike the volleyball roster, we can buy other new things that don’t fit into a “position” we already have filled. This happens ALL THE TIME! That’s why Category creation is SUCH A COMPELLING STRATEGY for a start-up. In fact, I’d go as far as saying it’s really the best one- full stop – drop the proverbial mic!
As I write this, I am sitting watching Owen’s practice with his new team. In sports, the best generational talents are often said to “Redefine their position” or “change the way that the game is played”. Wilt changed the center position, and paved the way for Akeem, Shaq and others, as did Michael and Lebron as well as Pele and Messi. They still are in the same category, the same position, but actually are 100x better. In business, the winners don’t change the way the position is played, they create a new position and change the game, not the way it’s played. In sport, that would be unfair, but in business it is actually #CategoryMagic.
TLDR: So here’s the not so long of it – I “dnf’d” at my “A” race. Finishing only 58/100 miles. Beautiful scenery, bitter disappoint and friendships old and new…
My post from that day kinda sums it up:
It’s now 96 hours later and I am so ready to NOT rehash the whole story of woe. Instead, I thought I’d do my top 5 highlights, the top 3 things I am proud of, and the things I learned. There are no top five lowlights, there is just one, and you saw it above! So let’s get to it
Top 5 Weekend Highlights –
Highlight 5: The whole event;
It is awesome. The expo, the vibe, the staff and the course. (Only small complaint was late start time for the 100 miler, 9 am, really???) Here I am at the start of the race, that’s as good as that got for me 🙂
Highlight 4: The people you know, meet and see:.
Top Row From Left to right: Dave M, my b-school classmate. Dave, me and Dave’s old buddies Joe and Gary at camp before the race, great hanging and riding with you guys!. Me and Menlo Park Neighbor Sam, owner and founder of Speedhound, great to meet you, let’s ride sometime!
Bottom Row: Me with Willie the Weiner Dog with owner and 3rd place men’s finisher Alexey Vermeulen and my coach and friend Ruben Bacon in center. Fanboy pic of Winner Keegan Swenson, superstar and 3rd place women’s finisher Flavia Parks, a neighbor kinda from Pleasanton. Reggie Miller out of picture but there.
Highlight 3 – Hanging with Dave
So awesome to have a weekend to chat and reconnect with my good friend Dave. He was an amazing host in Denver, along with his wife Dana who is equally awesome, and he wired the camping process and supply from end to end. THANKS SO MUCH!!! Here’s a shot on the road the next day (see highlight 1)
Highlight 2 – Dave and Joe’s Race Day Finishes
As I lagged on the course, the texts from Dave showed me he was having a great day. Essentially riding at my race pace goal, while I was lagging behind struggling. Dave did amazing, here’s his results from the site:
And Joe did pretty well himself, finishing his first ever 100 miler (and he says last :)) in under 8 hours.
So happy for both of these guys. You killed it! And all of you were very chill with me after when I was feeling pretty low. (Gary was not riding the race btw, and did the Rabbit Ears pass ride solo, or as Dave insists did a Rabbit Ear, I don’t get it though) Goals for next year to finish and to beat Dave’s time?
Highlight 1 – Vail Pass Ride on Monday
I felt mentally and physically like shit Monday AM. Horrible night sleep reliving my DNF and even cramping a bit, but the guys insisted we break camp, drive to Frisco and ride Vail pass. I was nervous about trying to climb on my cramping quads, and just mentally beat. But the peer pressure was motivating and I could not say no. Thanks guys! Up to the summit of Vail pass is actually fully paved wide path from Frisco, an “easy” climb at like 3% average and 14 miles. While Gary looked for his bike rack lock key (Story for another time, but a good one), Joe and Dave patiently rode slowly up the climb as I was tender on the quads and worried I’d cramp on the way up. I didn’t I made it:
and we enjoyed the scenery as Gary hauled ass to join us at the summit despite missing a few lower gears due to a mechanical issue in the rear.
After a ripping descent back to Frisco, I was all smiles and realized that riding a bike is fun, after a day of suffering on Sunday. Thanks for not letting me bail guys.
Top 3 Things I am Proud
#3 – I was ready to go, at least aerobically. Even at the lowest points, and when I stopped at 58 miles I wasn’t physically tired. That was one of the things that made it hard. My aerobic shape was ready, but the cramps (due to heat, altitude, dehydration most likely, position???) did me in. My engine was running great, but the pistons were literally freezing
#2 I made it to mile 58!, 30 + miles cramping. I did the best I had in me that day. Despite literally leg locking cramps which started at mile 25!, I gutted it up 3500 feet of climbing and made it more than halfway. Woulda been easy to quit sooner. And I felt ready too several times.
#1 I did quit when I did – At mile 58 I was at almost 5.5 hours with over 42 miles to go. It’s slower than I had ever been. But even more importantly, every time I made any effort I started cramping again. I was really emotionally spent. Several times before making it to the hydration stop at 58, I found myself losing concentration. In hindsight, the best case was to suffer for another 4.5 – 5,5 hours and finish in almost 11 hours and be absolutely dead, that is If I did not crash or go into full body cramping. It was just not safe. Despite the tears, I think it was the right call. That doesn’t lessen the disappointment, but I am trying to use it to strengthen my resolve to come back next year (if I get a spot) to finish what I started. Net net – Hard but right call
Things I learned or are still figuring out:
Gotta figure out the cramping. My hypothesis now is I was dehydrated at the start line, and even though I was drank over 6 liters of water in 5 hrs, exasperated by the extreme heat (90+ degrees all day) and altitude, I just never caught up. You CAN’T DRINK ENOUGH, AND OVER DRINK THE DAY BEFORE
It doesn’t go as planned, yeah i knew that, but a hard reminder.
Biking is fun (thanks Vail pass) and I need to keep it fun, even if I strive to improve. Maybe I put too much on this, I dunno still…
Well thanks for indulging me and reading about my fail! I still had a great weekend, and it still stings. They say biking is the hardest sport out there, and takes you high and low. I definitely felt that both mentally and physically. Next up is some easy riding and the local “Tour De Menlo” 100K fun ride and then a 2+ week 25th annivesry trip with my amazing wife Joel’ and without my bikes.
As for Steamboat, it’s still unfinished business for me. Hope to see your next year to finish what I started!
It started with a nice Thursday midday drive from the Bay area up to my AirBnB on the Truckee River, that is, until I noticed that my driving directions were telling me 1hr and 40 minutes for the last 45 miles. Hmmm, must be a crash ahead. Sure enough, just 9 miles from my destination, I hit this-
Not to be deterred, I ditched my car and mounted my bike, I wish. Despite the crawl to the AirBnb, I was so pleasantly surprised at the beautiful view and accommodations in my little home for the weekend –
From there, I walked the short distance to Downtown Truckee, and had an awesome pasta dinner at Jax by the Tracks, including a little extra carb loading, not sure Coach Ruben would approve of that, but he did sign off on the fueling plan for Saturday, composed of much less palatable but even higher carb options…as my friend Rich says, endurance events are really just eating contests!
After dinner, I met up with my friends Sally and Jon, for more carb loading at a local pub. No photo evidence for that little sidetrack. However, Sally and Jon did meet me Friday AM at the pre-ride with pro Anna Yamauchi . As you can see, Sally and Jon, who have a home in Truckee, fit right in with the Truckee crowd, where I look like a cycling tourist!!!
The pre-ride was anything but easy! Unfortunately, Sally felt a bit off, and Jon and she turned back not long after the start. I on the other hand was pleasantly surprised by the not so easy climb, and not so pleasantly surprised by the single track descent! I come to gravel from the road, and have next to no mountain biking experience, so I descended the “flowy” single track pretty cautiously. Anna pulled behind me and I got some nice tips on handling the terrain before we stopped for an uphill rider, and then I let the 7 or 8 folks who were piled up behind me pull on through. Here’s my Stava from that ride: (link here to see it live and follow me)
Pre-ride done, I went back to my AirBnb and out for a quick pasta meal before coming back and walking down to the river with my book and last carb-laden beverage. The river was running very fast, and the train roaring by and except for a few bugs, it was a nice way to end the evening before turning in early for the main event Saturday AM.
Race Day :
5:30 – Rise and shine
6a Breakfast of oatmeal and berries and coffee
6:30 – Fill bottles and USWE hydration pack, pack food
7a Dressed and ready to go
7:15a Out the door for the 1.8 mi spin to the start line
The race was epic!!!! I was doing the 54 mile route which was 45 time with a 9 mile roll-in. Here’s what it looks like, and here is the Strava route if anyone wants to do it themselves (which, with a few caveats, I highly recommend, on a mtn bike for reasons to come…)
As the graphic shows, the race was really 3 distinct sections, as demarcated by the rest stops, but in reality, for me, it felt like 4 (or kinda 5):
Section 1 the first 17 mile mixed terain “rollout” ending at rest stop 1.
Section 2: the roughly 10 mi climb leading to and up Babbit Road
Section 3: the 6+ mile descent climb descent ending at rest stop 2
Section 4: The paved then dirt 12 mile fast ride to the finish line
(section 5: the last 9+ miles of paved untimed “roll-in”)
Section 1 for me was uneventful save about 2 minutes spent on a dropped chain. After a hand from a course “Marshall” (BTW, the entire EventMonkey team and volunteers were AWESOME) I rolled into the stop averaging over 15mph, a good speed for me.
I was feeling awesome on the climb up Babbit, passing many riders and never felt too strained. Topping off at over 7K feet, I was quite pleased to see that neither the heat nor the altitude were causing me any distress or fatigue. Score one for fitness there!!!
Section 3 was BY FAR the hardest thing I have ever done terrain wise on my bike. Not being a mountain biker, the double track rock garden was so scary. I had to “pucker up”, take my time, and trust the bike. I managed not to death grip too much, and made it down with the toll of one stop to shake the hands, one waterbottle cage rattled off (remember to tighten those next time Ken!) and one cool picture, where I look a lot more controlled and calm than I was on the inside. Check it out:
The end of the long 6 mile descent, yes it was rocky
Rolling into the last rest stop, several of the pro men, who were on the long course, roared by me grabbing bottles on the way through. Having the descent behind me, I was feeling fresh and reading to ride hard on the last section. Ruben and I had targeted a “negative split” for this section of the course, and I managed to roll through to the finish line averaging 15.8 mph for the last 12 miles. It felt great.
Another highlight of the last section was catching up to my old friends Chris and Martina. We all worked together at Netscape decades ago, and I had ran into them at the start line. We rolled out together, but I lost them when I dropped my chain. With about 3 miles to go, I caught them and we had the fun of both rolling out and finishing together. SO FUN AND MEMORABLE. Here we are at the finish line and later stopping to ham it up in front of Boca Reservoir during the non-timed roll-in.
Friends, old and new, definitely was a theme of the weekend. It was really a pleasure to meet Haley Smith, the woman’s winner, at the finish line. Haley rolled in right around when we did after completing the long course, yes, that was 20 miles longer than mine, wow she’s fast!!! Haley, Chris, Martina and I had a great chat and she was friendly, funny, kind and gracious enough to pose for a picture with Martina and I. You are now my fave rider on the Gravel Pro Circuit, cheering for you Haley!!! (and Anna too, heal up from the crash and get out there so we can cheer for you!!!)
Sally and Jon who I really got to know better had done the short course, but waited at the festival to greet me, and then treated me to a super yummy meal at their home that evening. Here’s Sally and I at the festival, I am a bit dusty for sure!!!
Overall, I had a goal to complete the timed portion in 3.5 hours, including stops. Here’s my TrainingPeaks data for that portion of the ride. I “missed my goal” by almost 27 minutes. However, if I had known how technical the climbing and descending would be, I think I would have aimed more for like 4hrs. So overall, I was pleased with this finish. From a race perspective, I finished 22/34 in the Men’s 60+ and 132/198 in the overall Men’s finishers. Since this was my first race ever, and so technical, I am super pleased. I am on a journey to be a top 10 age group finisher, and this was a great first step in that journey.
Wrapping the ride up, here’s my Strava screen and link
After that amazing BBQ dinner at Jon and Sally’s I headed back to the AirBnb and my head hit the pillow hard. I was up bright and early and decided to skip the organized post ride ride and drive back home. The ride home was quick and uneventful, and I was left with nothing but awesome memories of the weekend.
Next up is my big event in Steamboat Colorado, 100 miles of “Champagne” Gravel on August 20th. I won’t miss the Tahoe rocks, and am excited for the longer and higher challenge of SBTGrvl. Until then, this OldManRolling will be training in the Menlo Park and the surrounding roads, trails and bridges. You can get more regular updates by following on Instagram @oldman.rolling Until then, keep the tires rolling – Ken
