Diane Stokes, "Iron Woman"


In college, Diane Stokes juggled caring for a sick mother, working full-time, doing ROTC and even had time to be on U Mass Lowell’s cheerleading squad. This energy and focus served her well as she progressed in her career of helping build startup after startup. Eventually, Diane founded a startup of her own. It succeeded beyond her greatest expectations. She invested as an angel for a while but is now back at another startup, helping them grow. My conversation with her revealed a personality of impressive determination and stamina leavened by good humor and genuine caring. I really enjoyed this interview, I think you will too.

Click here for the full episode transcript

Topics covered include:

  • Diane Stokes Bio
  • While in College, Diane Stokes Cared for Her Sick Mother, Worked Full-time, Did ROTC and Still Found Time to Be on the Cheerleading Squad
  • How Diane Stokes Found Her Path in Work Life
  • How Diane Stokes Juggled Her Transition from Engineering to Sales While Being a Mom and Getting Her MBA
  • Diane Stokes Left a Poorly Managed Startup and Went to a Second One that Got Acquired by Chipcom, a Particularly Well-run Company at Chipcom Diane Learned a Lot
  • Diane Stokes Realizes She Wants the Startup Life
  • Diane Stokes, Tri-Athlete
  • Sal Daher Reads an iTunes Review by TDN7 – Insightful Review
  • How Diane Stokes Founded her First Startup – Spoiler Alert: Moonlighting Involved
  • In Many Ways, ORP Was the Perfect Startup for Diane Stokes to Co-Found
  • What Diane Stokes Thought She Knew About Startups but Didn’t
  • The Most Useful Things Diane Stokes Learned from Co-Founding ORP – Number of Founders Is Critical
  • The Most Important Thing Sal Daher Learned at The Venture Café 😉
  • Why Diane Stokes Is Going Back to the Startup Life
  • Important Disclosure About Diane Stokes
  • Diane Stokes Has Joined Wireless Startup Wyebot Heading Up Marketing
  • Diane Stokes Gets Sal to Reveal the Exact Reason He Started the Podcast
  • Parting Thoughts from Diane Stokes

Transcript of "Iron Woman"

Guest: Diane Stokes, Startup Builder, Founder & Angel


SAL DAHER: Hi, this is Sal Daher of the Angel Invest Boston Podcast. If you've been listening, you might have noticed that I love being an angel investor in Boston. The reason for this is that there's so much going on in the startup space here in Boston. Practical founders working with leading inventors, venture capitalists, angel investors, patent attorneys, it's a really exciting scene. Now you can join us in syndicates, which allow people who are not part of the angel investment community to invest alongside Boston's leading angels. I invite you to leave your email address at angelinvestboston.com in the syndicate section, and we'll be back in touch with you to help walk you through the qualification process as an accredited investor. Remember, there is no obligation to invest when you put your email address there. I hope you really enjoy today's podcast.

SAL DAHER: Welcome to Angel Invest Boston, conversations with Boston's most interesting angel investors and founders. I'm Sal Daher, and my goal for this podcast is to learn more about building successful new companies. The best way I can think of doing this is by talking to people who have done it. People such as startup builder, founder, and angel Diane Stokes. Diane, I'm so glad we finally got a chance to schedule this interview. Thanks for coming in.

DIANE STOKES: Thanks, Sal.

Diane Stokes Bio

SAL DAHER: Awesome, awesome. Diane Stokes was the daughter of a single mom with frail health. Diane studied at the State University in Lowell, Massachusetts, a gritty former mill town. The choice of school was dictated by her limited ability to pay and the need to care for her mother in adjacent town. Which town was that?

DIANE STOKES: Chelmsford.

SAL DAHER: Chelmsford.

DIANE STOKES: Chelmsford.

While in College, Diane Stokes Cared for Her Sick Mother, Worked Full-time, Did ROTC and Still Found Time to Be on the Cheerleading Squad

SAL DAHER: Chelmsford, okay. Diane did what was needed to succeed. She lived at home in Chelmsford. She had a full-time job, and she also did ROTC. The latter by the way for those who don't know, entails early morning drills and extra classes in military science, etc., etc. It must have been a busy life. However, lest we peg Diane as an overly-severe workaholic, it's important to mention that she still found time to be a cheerleader. Her facility with numbers drew her to engineering, and she graduated with a degree in industrial engineering, a discipline that prepared her well for the opportunities that would come her way. Her career developed in unexpected and at times comical directions, which we will discuss later.

SAL DAHER: After helping build several startups to exit and three years teaching middle school math, Diane saw the opportunity to co-found her own company, Oncology Rehab Partners, ORP. Diane and her co-founder did such a good job at creating product market fit that she got an exit in year five to McKesson Specialty Health. After the exit, Diane began angel investing and joined Walnut Venture Associates, the angel group to which I belong. Now, she is going in an interesting direction that we will explore later.

SAL DAHER: My curiosity is piqued. So, Diane, it's a tradition in this podcast to dedicate the first question to how our hugely successful guests found their path in life. As I described in the introduction, you took a very interesting path. Tell us a story of you as a young mom, recently graduated in industrial engineering, not really trying to find a job, and you ended up getting your first job.

How Diane Stokes Found Her Path in Work Life

DIANE STOKES: Well, it was quite funny actually. I was looking for a job. It was 1989, and it was a hard time to get a job.

SAL DAHER: Oh, I remember that. Yeah.

DIANE STOKES: At U Lowell, I actually did the five-year Co-op Program in 4-1/2 years. So, I had some experience and work experience-

SAL DAHER: On top of ROTC?


SAL DAHER: Of all the full-time work.

DIANE STOKES: I was busy.

SAL DAHER: Yeah, I could imagine.

DIANE STOKES: So, we moved away for a year and then we came back to the Boston area, and I needed to find a job. So, I said, "You know what? I haven't interviewed anywhere. I need to get some interviewing experience." So, wherever I could get an interview, that's where I went.

SAL DAHER: So, you didn't want to find a job quite yet? You were preparing by training for interviewing?

DIANE STOKES: That's what I thought I was doing. Yeah.

SAL DAHER: Okay, right.

DIANE STOKES: So, there was a job for recruiter. I definitely did not want to be a recruiter, but I said, "Alright. Well, I'll go for that interview," and I got the interview. I had a great conversation with the guy, and he hired me on the spot. I was like, "Ah, sorry. I really don't want the job." He said, "Well, what do you looking for?" I said, "Well, I'd really like to use my degree, and I believe something in manufacturing or along those lines." He said, "Oh, I think I just got one of those." He opens his file drawer and he pulls out a file and he said, "Oh yeah. Here's one entry-level manufacturing engineer." I'm like, "That's perfect." So he made the call, sent over my resume, and I got the interview and got that job.

DIANE STOKES: So, moral of the story is just go for whatever opportunities come up. Yeah, so that's how I ended up. This was a fault-tolerant computing company. I was there for almost five years, but I only spent one year in manufacturing where I ended up managing the connection between sales and manufacturing for this OEM that we were working with. Then, the VP of sales for OEM he said, "Come work for me in sales," which honestly was a better fit for me.

SAL DAHER: OEM, meaning original equipment manufacturer. Somebody who manufactures stuff that other people used for a brand.

DIANE STOKES: Correct. We put their label on our system.

SAL DAHER: Your product?


How Diane Stokes Juggled Her Transition from Engineering to Sales While Being a Mom and Getting Her MBA

SAL DAHER: Okay. So, how did you juggle being a mom and making that transition from production to sales?

DIANE STOKES: I have an awesome husband. He too is great career guy but what we ended up doing was we were always there for our kids. That was number one, but we kind of took turns. We were really good at doing that. So, it was busy and I ended up going from my MBA at the same time in the mid-'90s. So, I had two little kids, full career, and going for that MBA. It was busy, but he was there and my in-laws came and lived with us to help with the kids during the week.

SAL DAHER: So that, you had a support system which is really great. What is it that led you to do that MBA? What is it you felt you needed from the MBA?

DIANE STOKES: So, at the time and I don't know if it's the same now, but when you went for engineering degree, we had very little English or business classes. My minor, I did in computer science actually. So, I didn't have any business experience at all, and I felt since I moved into sales that, that was the direction I was going to go and I wanted some experience and just to get some knowledge in the business field.

SAL DAHER: Oh, excellent.

DIANE STOKES: I went to Clark because frankly, just like my undergrad, it was the closest to me. It was a good school, and it ended up being great.

SAL DAHER: It was a very practical solution.

DIANE STOKES: My whole life has been very practical.

SAL DAHER: It had a part-time program that you could do.

DIANE STOKES: Yup, I did it at night.

SAL DAHER: By which time, you probably given up cheerleading.



DIANE STOKES: I was not a triathlete yet.

SAL DAHER: Yes. How did your work lead to discovering your true calling as a builder of startups, startups to exit, which is very interesting?

DIANE STOKES: The first company I learned so much about what to do and frankly what not to do. That company ended up going out of business. They had some severe management issues and whatnot.

Diane Stokes Left a Poorly Managed Startup and Went to a Second One that Got Acquired by Chipcom, a Particularly Well-run Company at Chipcom Diane Learned a Lot

DIANE STOKES: I left a few years before that happen, but I got an opportunity to build an OEM sales [at the second company], not department because it was just me, but group where I was building the sales funnel for this other switch company. It was a startup. It was smaller than the one I went to before. I really liked how I could do different things where, yes, I was responsible for OEM sales, but if something else had be done, I got to do it. So, I got exposure to a lot, both at my first job and my second. I never said no to anything anyone asked me to do. That [second] company was bought by another switch company, so I went to that one, which was probably the best managed company I've ever been at, and that was Chipcom. We still have reunions and whatnot.

SAL DAHER: Oh, excellent.

DIANE STOKES: Yeah. It was just a phenomenal group of people. Again, learned a great deal from that company and was then bought by another company, which is a larger one. I only spent maybe a year at that much larger company, and I just realized then that I'm a startup person. I don't like being pigeonholed into a job, and I don't like all the politics and whatnot that go on with larger company.

Diane Stokes Realizes She Wants the Startup Life

SAL DAHER: Excellent, excellent. That is really important. That realization came relatively early in your career that this is what you're cut out to do. You are a startup operator and that's what you're going to do the rest of your life.

DIANE STOKES: Yup, I did. I consciously, that was the first time that I made that conscious decision. I really didn't think about it. I was just doing a job, but then I would think back about what I liked about jobs that I was doing.

Diane Stokes, Tri-Athlete

SAL DAHER: Diane, what part does being a triathlete play in your maintaining your grueling piece of work. For those not familiar, a triathlete competes in contest where swimming, bicycling, and running events follow each other and they're measured in their overall time including transitions. So, I'm thinking, "Yeah, geez! She's a process person and understands all this stuff. So, she's probably really good at the transitions."

DIANE STOKES: I'm best at the transition.

SAL DAHER: You're the transitions pro.

DIANE STOKES: I am the transition queen.


DIANE STOKES: I actually did not get into triathlon until I was 37.


DIANE STOKES: So, I worked out at a gym or whatever, but I didn't find it until later, but now, having done ... I'm actually doing my fourth Ironman in a weekend. Having done multiple long, long races, it's kind of like being at a startup.


DIANE STOKES: The stamina you need and the mental fortitude to keep going is all startups are. Yes, you have to have a great idea. Yes, the team is critical, but being able to mentally keep going day in, day out, a week, month, year, it's critical to being successful in a startup. Things happen and same with triathlon. Things happen especially in a race like an Ironman. It takes anywhere from 11 to 16 hours. Something's going to happen and you have to be able to deal with that, and the same is true for startups. Every week, something weird or something that you just did not think about is going to happen, and how you deal with that will determine your success in completing whatever it is you're trying to complete.

SAL DAHER: I guess you're saying that running a startup is not a sprint?

DIANE STOKES: It is not a sprint. It feels like a sprint because your adrenalin is running all the time. I must be an adrenalin junkie or something that.

SAL DAHER: Yeah. You must drink a lot of coffee?

DIANE STOKES: No, I don't actually.

SAL DAHER: Oh, you're pre-caffeinated already.

DIANE STOKES: I only drink caffeine on race morning, so that I get that extra jolt.

SAL DAHER: Oh, awesome.

DIANE STOKES: I drink a lot of water though.

SAL DAHER: I understand. Now Diane, you worked for two decades in one startup after another. As soon as one got acquired, you went looking for another startup to work in and to revive. Why? What did you get out of working at these struggling enterprises? I mean, why shop for headaches. I mean, you could have gone into a cushy job in one of the acquiring companies. Why stay with the startups?

DIANE STOKES: I tried that. I tried doing the cushy job thing and it's not for me. I like change. You mentioned I taught math for three years, which I loved. I love the middle school math like those kids. You can really make a difference in their lives and I really, really liked it. I thought I was going to stay there. I took 18 education credits at a local school just to get better at it. I thought that's what I would do, but I got restless. I need that change and that ... I don't know. I guess it's adrenalin. I don't know. I like change. I really, really enjoy being in the startup environment, and the excitement and the pulse of it. I'm not afraid of hard work. I've done it my entire life, and I get bored when I'm not working hard.

Sal Daher Reads an iTunes Review by TDN7 – Insightful Review

SAL DAHER: Great. Amazing, amazing. Coming up next, I will ask startup Ironwoman Diane Stokes about what led her to found her first startup. First, I wish to thank listener TDN7 for this great and very perceptive review in iTunes. "I have listened to several of Sal's discussions and look forward to hearing the rest. We get to sit in on private discussions between people who have collaborated already, and are now getting to know each other on a deeper level. Many familiar topics are covered like pivots and the comparison of Silicon Valley, and the Boston angel investing approaches, plus there are many surprises like Sal's diversification of rewards approach to his portfolio and the fact that it can sometimes be best to broaden interests instead of focus. Thanks, Sal."

SAL DAHER: TDN7, it is I who owe you a debt of gratitude for leaving a review of such perspicacity. You uncovered my secret method for choosing guests. Choose people with whom I have enjoyed working, and I just want to get to know better such as Diane. Listeners, take the example of TDN7, and give back by leaving a review on iTunes. The Angel Invest Boston Podcast has great guests like Diane Stokes. It is professionally produced and is totally free of commercials except for this one. The only thing we ask in return is that you help get the word out. Please tell an angel or founder about us. Sign up at angelinvestboston.com to be notified of free upcoming events where you can meet people of the caliber of Diane Stokes and my other guests.

How Diane Stokes Founded her First Startup – Spoiler Alert: Moonlighting Involved

SAL DAHER: So, Diane, you were giving back a little by teaching math to middle schoolers for three years, and then you got the itch to work at a startup, and then what happened?

DIANE STOKES: So, a previous boss called me in my third year of teaching and he said, "Diane, I really need your help. Can you come help me build the marketing department of the company I'm at?" I'm like, "Oh, I don't know. I really want to do something on my own that kind of gave back." He's like, "Oh, come on. You can do it." I ended up going there. I said, "Look. I'm going to stay one year. I'll help you start it, and then we'll hire a team and then I move on." Four years later, I was still there.

DIANE STOKES: What ended up happening is my neighbor came down with cancer, went through all their treatment. She's actually a physiatrist. So, she basically rehabbed herself, and she looked at the care she was given, before, during, and after her treatment. She said, "This cannot be the standard of care. I know what to do because I'm a physiatrist. How can I help other cancer survivors?" We were bringing meals to her, then things neighbors do. We start talking, and I said, "Well, this is what I do. I productize things. I'm a startup person and let's talk about this." So, we spent about three months really thinking about what we could do. How do we productize it? What is it?

SAL DAHER: While you were working at-

DIANE STOKES: While I was working at my last company.

SAL DAHER: At the last company, okay.

DIANE STOKES: Yup. So, that was January. We start talking to some customers, potential customers. She had connections into hospitals and other physicians. We decided, "You know what? We can do this." So in June, we incorporated. At that time, I went to the management of the company I was at and I said, "Look, I'm going to found this company that is going to help cancer survivors, and I'd like to go to three days a week," and they let me do it. I had a great team that I had built in marketing, and I knew that I could do that and they could still be successful.

DIANE STOKES: So, that was in June. Then by October, November, we were so busy at the startup. It was nights, weekends, anytime I was not at my other job. I said to them, "Can I go to one day a week just to check in, make sure everyone's all right?" They agreed to that. Then, that lasted a month and I just said, "You know what?" December came and I said, "I need to build this other company." So, we parted ways but I really thanked them for how flexible they were, and they really wanted me to be successful because it was such a great company to help people.

In Many Ways, ORP Was the Perfect Startup for Diane Stokes to Co-Found

SAL DAHER: What I'm thinking here is that it makes a lot of sense given your background. You're caring for your mom when you're in college, and you're doing all these things. So, you're good at juggling a lot of things, but at the same time a compassionate mission, it's just exactly your wheelhouse.

DIANE STOKES: It really was, and we really meshed well because she knew the product and the market, and I could build the business side and day-to-day operations, get everything lined up, and help productize what was in our head; nothing was on paper yet. That's frankly how we started with PowerPoint. Then, we got two hospitals that first year that were really on the leading edge, and we're able to help them create service lines, and the service line is helping to navigate patient care. So, we were able to do that in one of those hospitals, was one of the leading hospitals in cancer care. So, it really helped catapult it.

SAL DAHER: How did you get paid for that?

DIANE STOKES: We get paid?

SAL DAHER: ORP {Diane's startup]

DIANE STOKES: That was part of the process, finding out what they were willing to pay. So, our firsts couple of clients, we either did at no charge or did at a reduced price. Then as more came on, we were able to more refine what the pricing model would be, and it was a recurring-

SAL DAHER: The hospitals are paying for that?


SAL DAHER: Interesting.

DIANE STOKES: Yeah, not an easy sale, the hospital.

SAL DAHER: I can imagine. I can imagine.

DIANE STOKES: Well, I mean with my co-founder's experience in the field, she was known in this area, which helped a lot. She did a lot of speaking in cancer rehab.

SAL DAHER: Okay. So how do those two decades of being in the startup milieu made you, help you with your Oncology Rehab Partners Company, ORP?

DIANE STOKES: Yes. So, as you say, I was immersed for 20 years in startups and you learn a lot if you just need to keep your eyes and ears open in all departments actually. So, I knew what I didn't know. So legal, accounting, I was not going to fool around with that, hired outside help for that, made sure that the systems were in place, so that we did everything above board and what not. I worked at a lot of companies, and as I said I'd leave one place and get acquired by another, and so it was a lot of experience and different people and mentors. People can be mentors without officially being your mentor, right?

SAL DAHER: Mm-hmm (affirmative).

DIANE STOKES: So, you just need to listen and ask questions, and I learned a ton at these different startups.

What Diane Stokes Thought She Knew About Startups but Didn’t

SAL DAHER: You mentioned that you were not prepared for stuff in legal, and so forth. That stuff you knew you had to subcontract out so to speak. What was it that you thought you knew but you'd really didn't know? Was there anything like that?

DIANE STOKES: One of the advice I would give is not to start a 50-50 partnership.

SAL DAHER: Mm-hmm (affirmative).

DIANE STOKES: We were very complimentary. However, as things go on, there are problems that come up or problems that you need solutions for, and if there's a kind of a difference of opinion, there's no one to break the opinion. So, I would definitely suggest that ... I personally would never do another 50-50. Odd numbers are good.

SAL DAHER: Yeah, 51-49 so that-

DIANE STOKES: Even that I think it would create animosity. I would go with odd number of founders versus even number of founders.

SAL DAHER: Okay. Odd number of founders. Did you have a board in those days?

DIANE STOKES: We did not, which was another ...

SAL DAHER: That's where it might have helped, to have a board.

DIANE STOKES: Yeah. We were self-funded. We were building something for the good of society, and it grew much larger than I think even my co-founder thought it would grow.


DIANE STOKES: So, it became a real company, and yes we needed a board of directors.

SAL DAHER: Am I right in assuming that you have product market fit early on, but the challenge was how to scale economically?

DIANE STOKES: Yes, product market fit was obvious. The interesting thing too is that there were no requirements for rehabilitation after cancer care, and that was one of the things we were able to do at our company is change the requirement of hospitals that they had to provide cancer care.

SAL DAHER: So, you changed your market, interesting.

DIANE STOKES: Doing so, working with the agencies like Commission on Cancer, etc., they put in requirements for rehabilitation and nobody was providing it. So, the hospitals either had to do it themselves or they hired us to do it.

SAL DAHER: You said that you didn't have any venture funding, or anything like that, or angel funding but you did get some funding later on. How did you get it actually?

DIANE STOKES: Right. There was a gentleman who has a fund, and he invests in many different things, and cancer was one of the things that was near and dear to his heart. So, he actually gave us a loan at favorable terms, and we had to pay it back in two years, but the interest rate was low for the times and he didn't ask for any equity or anything.


DIANE STOKES: I'm trying to remember how he came to us. I think it was through somebody that my co-founder knew.

The Most Useful Things Diane Stokes Learned from Co-Founding ORP – Number of Founders Is Critical

SAL DAHER: What did you learn that you think is useful to other founders from these remarkable experiences?

DIANE STOKES: First thing is to keep moving forward, making decisions quickly and accepting that some may be wrong is really important, because if you stop and think about things for too long, opportunities going to pass you or you can't move forward and grow the way that you need to.

SAL DAHER: Yeah. I didn't figure you'd be a big one for analysis paralysis.

DIANE STOKES: I was not, no. Also, not letting those wrong decisions fester.


DIANE STOKES: Accept them, admit them, admit that it was wrong, and again correct it, move forward, not festering. The other thing as I alluded to before is not skimping on critical things like accounting and legal.


DIANE STOKES: You can really get into big trouble if you don't do those correctly.


DIANE STOKES: Unless you're an accountant, I would not do that on my own, and unless you're a lawyer, I wouldn't do the contracts and whatnot on my own as well. Yeah. Setting up contracts with your co-founders, we did that from the get-go, and it was critical. So, you really, really need to take time upfront to do that.

SAL DAHER: Working out the relationship between the founders and so forth?

DIANE STOKES: What happens if, yes.

SAL DAHER: That's excellent.

DIANE STOKES: Another critical thing I would say is that 50-50 ownership, and even 49-51 as you had said with two founders I think would create more animosity.

SAL DAHER: You're only a 51% owner, and you're rolling over my ideas.

DIANE STOKES: Exactly. I just ... I would not recommend that.

SAL DAHER: Yeah, interesting. I'm thinking back Ed Roberts talking about the number of founders. One is very tough, two is much better, three is even better.



DIANE STOKES: I like his five rule.

SAL DAHER: Even five, if you ... Up there, he says it's not statistically significant, but there is a trend there that makes you suspect that it still helps. Also, commonality of value so to speak, both of you were interested in doing something about this big lack in rehabilitation after cancer treatment.

DIANE STOKES: Right. The funny thing about the values, until you get into business with somebody, it's not really values that may come out but differences in how you approach things, and you don't know that until your full in on a company. So, having more than two even three-


DIANE STOKES: ... is why that's so important as well.

SAL DAHER: That is tremendous. So, let's talk about your angel investing. Sold your share of the company and you were living in a place where you can't swing a dead microcircuit without hitting a startup.

DIANE STOKES: Yeah. So, my husband and I had never lived in the city. We decided to buy a condo and we lived there for three years and just immersed in the startup ecosystem in Boston, which was a blast. I joined Walnut. I was able to judge and mentor at MassChallenge, go to the Thursday night. One of those events that-

The Most Important Thing Sal Daher Learned at The Venture Café 😉

SAL DAHER: The Venture Café, that's at CIC, yes.

DIANE STOKES: The Venture Café where tons of startups ... So, I really got to immerse in that environment and it was great, and so we found a couple of companies to invest in. We talked to, I'd say-

SAL DAHER: You mentioned, if you just to say ... One of my interruptions and my daughter will probably chastise me for. When I think of Venture Café, one of the things that I learned from Venture Café is never drink fast any beer product that has imperial in it because it means it has a lot of alcohol.


SAL DAHER: I didn't know that.

DIANE STOKES: What did you do?

SAL DAHER: I downed it. Yeah, an imperial stout and I was almost had to be taken home.

DIANE STOKES: Oh, that's hilarious.

SAL DAHER: After that, I'm very ... Anything has imperial or drubbel, or triple, or quadruple whatever.

DIANE STOKES: Don't drink it.

SAL DAHER: Yeah, just drink as if it were wine, strong wine.

DIANE STOKES: My [crosstalk 00:27:42].

SAL DAHER: I've learned other things at Venture Café.

DIANE STOKES: Yeah, that's important. Mine is not to drink at all because I have two sips and I'm like that.

SAL DAHER: So, you were in this environment steering clear of the imperial stout at the Venture Café and meeting people there, and you were advising at MassChallenge and so forth, and you found that initially exciting?

Why Diane Stokes Is Going Back to the Startup Life

DIANE STOKES: Yeah, it was great, talking to really excited founders and people that want to start companies, and all the different companies that people were starting it. I felt like I was in my bubble when I was at my own company. I only knew what I needed to know because there was just ... We were working 24/7. I had to learn the healthcare industry, and you only know what you need to know, right?

SAL DAHER: Mm-hmm (affirmative).

DIANE STOKES: So, I felt like I was in a bubble and I didn't really know what was going on in the ecosystem, and so that was a lot of fun to understand all the different companies that were being started, and the different technologies, and what was going on in the real world.


DIANE STOKES: So, yeah that was great, but then my personality kicks in, and I don't like being on the sidelines. You can-

SAL DAHER: Why should those startup artists have all the fun? I want to get in there.

DIANE STOKES: I know, but the thing is I didn't have an idea that was good enough to launch my own company.

Important Disclosure About Diane Stokes

SAL DAHER: Let me just fill in something for the audience. Audience, a little disclosure is in order. Normally, we conduct this interview sitting down. Diane, pleading that she had been sitting in a car for two hours is conducting this interview standing up. I think it's a little bit indicative of her attitude. She doesn't want to be on the sidelines. She wants to be active and engaged.

DIANE STOKES: Well, not pacing like I normally do.

SAL DAHER: Right. As a concession to me, I think she probably would have rather had this interview while we're strolling or jogging somewhere.

DIANE STOKES: That's true, biking probably.

SAL DAHER: Biking, but she made a concession. So, she's just standing, but anyway I thought that disclosure was important; in her bare feet. So, please continue. You were saying, "Geez, this is great. I see all these things but these people are doing all the stuff, and I don't have an idea." Then, what happened next?

Diane Stokes Has Joined Wireless Startup Wyebot Heading Up Marketing

DIANE STOKES: I was networking like I normally do just talking to people that I used to talk to, and I was having coffee with a guy I used to work with at one of the 90s companies. He had started a company, and he was two years in but that was from product development and this is a wireless company. So, you know it took some time to get the product right. So, it's a bunch of engineers. There, we have a real office and real product now, and some lots of demos going on, and he need to take it to the next step on the marketing.

SAL DAHER: What company is that?

DIANE STOKES: It's called Wyebot

SAL DAHER: Wyebot, yes, yes, I saw that.


SAL DAHER: What is Wyebot doing?

DIANE STOKES: So, right now wirelesses is just not reliable. It's hard to figure out where the problems are, and so they can automatically detect where the problems are and provide solutions to that. They can also help performance by looking at all the internet of things in VOD [Video on Demand] devices that are on the wireless networks for different places like education institutions, so colleges, higher education, enterprises, smaller enterprises that are doing their business on wireless basically.


DIANE STOKES: Customer service and connection is critical to them.


DIANE STOKES: So, they're making great headways, products ready.

SAL DAHER: Awesome. Yeah, I saw that they had a raise in 2016, 600k.

DIANE STOKES: Yeah. So, they've raised a total of I want to say two million and they're going for their seed series now.

SAL DAHER: Having raised two million, they're going for the seed series.

DIANE STOKES: Yes, the markets changed a little bit-

SAL DAHER: I know.

DIANE STOKES: ... where VCs are not coming in until the three to five million range.


DIANE STOKES: Yeah. So, and they have a lot of interested investors, and so they're just going to go with that for the next few months and-


DIANE STOKES: ... move forward, but lot of traction. So, I'm helping them on their marketing right now, which I love being around this great group of people. They're so smart. Actually, quite a few of them I worked with at the previous company 20 years ago. So, they have a ton of experience. I really enjoy it, and I'm enjoying being in the thick of it again.

SAL DAHER: So, it leaves no time for angel investing. This is not an unusual thing.

DIANE STOKES: It's not. I thought it was just me because-

SAL DAHER: No, no, no. I mean, look what happened with Steven Ladd.

DIANE STOKES: Yeah. True, yeah.



SAL DAHER: Look what happened with Lucinda. While she was sidelined because she had kids, so she was out of Walnut at the time but she got pulled into Squadle.


SAL DAHER: The marketing side of things.


SAL DAHER: It's not an unusual thing and you're a young woman, and you have a lot of energy and so forth, and you've learned a lot, but you still have all this energy to actually get a startup off the ground, which is ...

DIANE STOKES: Yeah. I love it, and hopefully I'll come up with my own idea or co-found again with-

SAL DAHER: I have no doubt that you will.

DIANE STOKES: ... several people, not two.

SAL DAHER: When you do, I hope that you come back on the podcast and tell us about that.

Diane Stokes on Why and How She Listens to Angel Invest Boston

DIANE STOKES: Definitely. Absolutely. The podcasts are great by the way. I've listened to every single one of them-

SAL DAHER: Oh, I'm so [crosstalk 00:33:06].

DIANE STOKES: ... while I'm running. Actually, I do that.

SAL DAHER: Isn't it? Yeah, I timed it so that they're one work out or one commute roughly.

DIANE STOKES: Yeah, they're great.

Diane Stokes Gets Sal to Reveal the Exact Reason He Started the Podcast

SAL DAHER: That's the most frequent use case people mention is that commute or a workout. It is just such a great medium to be able to have a conversation with someone. After the podcast is recorded, the sound engineer Raul, edits it and takes out all the [lip smack], and the coughs, and all the stuff, so it sounds really good. Then, I send it to the guest to make that sure the guest is okay. There are no bloopers in there that they want to take out, and then I send it to a transcriber, Rev.com. They transcribe it.

SAL DAHER: Then, I sit and I read the transcript with a headset on, and I listen to the podcast. I stop it, and then I listen to it again and then I make notes, which are the subject headings. So that in every podcast episode, we'll have the transcript with my notes, with my headers, pull quotes, or whatever and this is where I learn.

DIANE STOKES: Well, you're doing a great job. They're fantastic.

SAL DAHER: For me, it's a learning exercise.

DIANE STOKES: Why did you start them?

SAL DAHER: I was going to due diligence meetings with people like you and I would think, "They know so much that I don't know." I haven't had the experience you had of getting the startup running and so forth. I spent 25 years in a trading room looking for bonds that were mispriced, okay?


SAL DAHER: Then, figuring out ways to buy those bonds and then to sell those bonds and so forth, to trade them. It's a startup in a way. It was a new product every few weeks. So, I mean we were doing very rapid prototyping, so to speak and figuring out markets very quickly and so forth, but it's not the real world. It's a very abstract thing. You don't have the problems that you had with the production line, and like a ship getting stuck in a port in LA or something, when you're dealing with bonds. I mean, there are assassinations. There are coup d’états. There are things like that. This is in the country space.

SAL DAHER: So, I said, "These people know so much more than I do about how hard it is to build a software product? How hard it is to build a physical product? How never to invest in a device company?" I didn't know that. I was dumb. Four years ago, I was at device companies, "Oh, that's very interesting." Now, somebody has-

DIANE STOKES: Every startup sounds great, doesn't it?

SAL DAHER: It does and now, I wasn't stupid enough to do it on my own. I would always sort of bring people in who knew a lot more than I did, but then I started to see, this is the way to learn. I sit down with them. They're always interesting people. They're always enthusiastic, and very well-spoken, and very incisive minds. I get smarter with every episode. I love this.

DIANE STOKES: That was great. That's awesome. I'm glad you're doing it. There is so much knowledge out there and the transfer of knowledge is critical, and this is such a great medium for it because you can listen to it at any point.

Parting Thoughts from Diane Stokes

SAL DAHER: To sum up the interview, please take a moment and think of anything that you'd like to add that we didn't touch on, and that you think is worthwhile pursuing?

DIANE STOKES: I believe knowing what you don't know is super critical.


DIANE STOKES: That it will always be harder than you think it is.

SAL DAHER: Okay. So, explain what you mean by knowing what you don't know.

DIANE STOKES: Yeah. So you said, well, I always surrounded myself with people that knew more than I did in certain areas. So knowing what areas you need help in is critical.


DIANE STOKES: So, bring in those people that can help you whether it's consultants, or co-founders, or employees or whatever, and startup is not for the faint of heart. You need stamina.


DIANE STOKES: So, it will be harder than you think it is. It's all fun and games the first year, two, but when you start really making traction or not, right? So if you're not, get out immediately, but if you are, it is only going to get more difficult.


DIANE STOKES: So, having that stamina and knowing that it's not a sprint.

SAL DAHER: You know, I've heard similar things from another young founder Matt Singer that I have interviewed, and who's going to be ... By the time this episode is launched, his episode would have launched and he was saying exactly the same thing. He says that there's no heaven that you reach. There's no situation of perfect peace and tranquility. You got your seed round, and you get your first money, and it's just insane. You're going like crazy, and then you manage to figure out one vertical, and you go and you get your Series A venture money. Then, you're even under the gun even more because the venture capitalists, they'll breathe down your neck.

DIANE STOKES: You have to answer to them.

SAL DAHER: You have to have this unbelievably fast growth and live up to that. So, it's like the ante gets upped at every turn and thus we advise really, really good cardiovascular health for founders.

DIANE STOKES: Yes. It helps to ... I do my best thinking while working out. The problem is when I'm swimming, I have nowhere to write it. Then, so I get out and I forgot what I ... my great idea I had but yeah, definitely helps to work out.

SAL DAHER: That is tremendous, Diane Stokes, Ironwoman. I'm so grateful to you for fitting in this interview before you launch in your new phase in life.

DIANE STOKES: Thanks, Sal. No, it was great. I'm so glad I did it.

SAL DAHER: I'm sure our listeners are as inspired as I am by your amazing life. Listeners, if you enjoyed this podcast, please review it on iTunes. Write to me at sal@angelinvestboston.com with critiques or suggestions. You will find transcripts of this podcast at angelinvestboston.com. Do sign up for future in-person events. This is Angel Invest Boston, conversations with Boston's most interesting angels and founders. I'm Sal Daher.

SAL DAHER: I'm glad you were able to join us. Our engineer is Raul Rosa. Our theme was composed by John McKusick. Our graphic design is by Katharine Woodman-Maynard. Our host is coached by Grace Daher.